Shipping back to Boston & a final cost tally (Nick’s 100K Vacay journal)

I am publishing this post from 36,000 feet to share a full tally of the final costs from my 100K Vacay. Read on for that last update and join us tonight for a live podcast recording recapping 100K Vacay and hearing the judges declare a winner!

Totals

This morning, I woke up in Sofia, Bulgaria, checked out of the Hilton Sofia, took public transit to the airport, and after visiting the Aspire lounge in Sofia, I boarded a Ryanair flight from Sofia to Madrid. That flight was inexpensive ($86.59). I’ll note that the Ryanair flight was the only of my flights that didn’t allow for a free carry-on bag in addition to a personal item. I didn’t intend to bring more than my backpack anyway for this trip.

Adding it all up, the following chart shows my total costs for my 100K Vacay:

Item	Points Spent	Cash Spent
Thursday
Iberia flight BOS-MAD	5000*	$91.38
Friday
Flight MAD-AGP (missed)	0	$60.80
Flight MAD-AGP (make-up)	5K	$26
Transit into Malaga	0	$2.13
Transit to/from El Chorro	0	$10.33
Transit (shuttle to Caminito del Rey)	0	$2.96
Water purchased after hike	0	$2.34
Dinner (Too Good to Go)	0	$3.91
Palacio Solexcio, SLH via Hilton	24K**	0.00
Saturday
Rental car	0	$24.59
Tolls	0	$12.92
Windsurfing class	0	$88.77
Dinner (Too Good to Go + grocery store wine/cheese)	0	$12.33
Hilton Garden Inn Malaga (Points & Money)	9K***	$70.37
Sunday
Gas for rental car	0	$18.62
Flight AGP-BEG (to SOF)	0	$110.79
Transit (shuttle BEG to city)	0	$4.04
Saint Ten Hotel (cash portion of points & money)	17K**	$41.87
My portion of dinner in Belgrade	0	$22.97
Monday
Transit (shuttle city to BEG)	0	$4.04
Transit (Sofia airport to hotel)	0	$0.95
Poker	0	$100.00
Hilton Sofia	16K	$0.00
Tuesday
Lunch	0	$15.46
Free walking tour tip	0	$5
Hilton Sofia	16K	$0.00
Wednesday
Transit (Hotel to Sofia airport)	0	$0.95
Hotel city tax & snacks from lobby shop	0	9.30
Flight SOF-MAD (Ryanair)	0	86.59
Flight MAD-BOS (Iberia award)	8K*	127.11
Total	100K	$979.63

*Note the Iberia flight to Madrid was booked with 6,400 Avios and the Iberia flight from Madrid to Boston was booked with 10,000 Avios. Thanks to a previously available 30% transfer bonus to Avios, these flights only cost 5K and 8K Avios, respectively.
**Note: because of the 25% transfer bonus from Amex to Hilton, each of the Membership Rewards totals should be multiplied by 2.5 to see the number of Hilton points redeemed. Further, the Hilton Garden Inn Malaga and Saint Ten Hotel Belgrade were booked with Points & Money, hence the cash portion. That cash portion was paid with separate cards with quarterly Hilton credits, but those rebates are not figured into the total spend here.

As a reminder, that got me:

• Flights to, from, and around Europe to visit 3 countries
• 5 nights in hotels (two of those nights in centrally-located luxury boutique properties, and 2 nights in a hotel that was perfectly-located for my purpose (a ten-minute walk from the casino in Sofia)
• Several cool activities
• Local transit & food

For those curious about the cash prices of the flights and hotels that I booked as awards at the times when I booked them:

• Iberia BOS-MAD round trip nonstop: $1,631*
• Palacio Solecio, SLH hotel: $511.06
• Hilton Garden Inn Malaga: $188.46
• Saint Ten Hotel Belgrade: $251.92
• Hilton Sofia: $711.56 (total for both nights)

That means I got the following point values:

• 10.87c per point for flights ($1631 – taxes & fees paid = $1412.51 / 13,000 Amex points redeemed)
• 1.78c per point for hotels ($1661.82 – cash portion of points & money = $1,549.58 / 87,000 points redeemed)

I should note that the cash price of the exact round-trip Iberia flights I booked from Boston to Madrid was very high at $1,631. Connecting itineraries were available for a bit less than $500. However, it would have been impossible for me to book a connecting itinerary because none of those would both depart Madrid late enough for me to get to Madrid from Sofia in time and get me to Boston before the 9pm live check-in. In other words, I 100% needed the nonstop Madrid to Boston flight in order to have enough time to get to Madrid (and the Ryanair flight was a perfect fit since it was scheduled to arrive 4 hours before my flight to Boston, which was a comfortable margin). I have accounted for the value here based on the nonstop flights since I definitely needed that on at least one end (and pricing out itineraries that connected en route to Madrid but included the nonstop on the way home were still similarly-priced to the nonstop round trip).

I am enjoying the spirited debate in the comments about what you liked and didn’t like! My aim here was to show just how much possibility lies in just 100K points by planning an epic vacation within the parameters we set out, using those points and an amount of cash that many people would find entirely reasonable for an “average” vacation to plan a vacation that seemed anything but average. Even as someone who writes about this stuff for a living, it amazes me that at least two of us (and presumably Tim also) were able to fly to Europe, eat and sleep for 5 nights, visit multiple countries, and do a number of activities that brought us joy (and in some cases probably surprised you and each other) with the budget we had set!

Overall, it has been a terrific week. As I type this, my flight is inching toward Boston. I look forward to discussing this further on the live stream tonight at 9pm Eastern!

October 7, 2025

I have been having a fantastic trip thus far, but I have to admit that burning the candle at both ends does eventually start to accumulate. For instance Comm when I arrived back at my hotel last night around 2:45 AM, rather than go to sleep, I was writing a journal entry In thinking about which clips to send to Carrie to tell the story on Instagram. By the time I got done with the tasks I needed to do, it was nearly time for the hotel restaurant to open for breakfast. I decided to just stay awake long enough to eat, then return to the room and catch just a couple of hours of sleep before getting up to tackle the day.

So I hit up the breakfast buffet early. I was pretty impressed with the Hiltons breakfast spread in the context of being a European hotel. Breakfast at major chain hotels in Europe almost never holds a candle to breakfasts in Asia or the Middle East. This one was better than most European buffets though. The Hostess highly recommended the omelet and seemed disappointed when I told her that I don’t care for omelets. However, they had some breakfast meats and cheeses and grilled vegetables, a number of types of pastries, Fresh yogurt, and a Bulgarian pastry dish called Banitsa. I certainly didn’t leave hungry.

Then I shot back upstairs to sleep for a couple of hours, setting my alarm just in time to get up and pull myself together for my scheduled Free Sofia walking tour at 11:00 AM.

Most European cities have free walking tours. That’s a fact that I think my wife and I learned around 2010. I have always wanted to do one, but despite having known about the free walking tours for so many years, we have somehow managed to never actually do one! The kids have been our excuse for the past 7 or 8 years, but I can’t really tell you why we never did one before that. When I realized that the poker tournament Day 1 would start at 4pm, the very first thing I did was seek out a free walking tour to finally be able to take advantage of one here in Europe!

The tour started at 11am, and my alarm got me up at 10:25am. It took me a couple of minutes more than 10 to pull myself together, so I looked at my options to arrive at the starting point by 11. Public transit would have taken 16 minutes, versus walking taking 25 minutes, according to Google. The time savings didn’t seem significant enough so I decided to just walk it to the tour starting point and pick up the pace. With a little hustle, I managed to still arrive right as the clock struck 11.

I am so glad that I did this free walking tour. The tour guide, Stefan, was born and raised here in Sofia and was an absolute wealth of knowledge. He challenged us to ask him any question, claiming that if he didn’t know the answer, it must be an irrelevant piece of information :-). Truth be told, he did confidently answer every question someone asked. And I learned so much! I quickly realized that I knew relatively little about Bulgaria’s history. He showed us Roman ruins, explained the religious makeup of the country while pointing out places of worship, and talked about the complicated political history of Bulgaria from World War II through the years as part of the Eastern Bloc. It was all fascinating!

I even learned that I’ve been saying the name of the city incorrectly. Stefan told us that in Bulgarian, they both have the name Sofia as you probably pronounce it (so-FEE-yuh), which is a female name, and the name of the city, which is pronounced SO-fee-yuh, with the emphasis on “so”.

The experience you get on a free walking tour probably highly depends on the tour guide you get, and I don’t think you usually get a choice. Still, this was a great one. Our tour group included people from Norway, Croatia, Italy, Greece, the Netherlands, Germany, Colombia, and the United States.

The tour lasted for about one hour and 45 minutes and left us further away from the hotel than the starting point of the tour. As a result, my walk back to the hotel was scheduled to take about 30 minutes. I decided that I wanted to try to get something for lunch that felt traditional and common. During my walk to the hotel, I stumbled on a sort of Bulgarian fast food chain with the initials BDS, standing for Balkan grilled delicacies. They serve many of the dishes that most lists tell you to try when in Bulgaria.

I should note that one potential problem is that many restaurant names and menus are printed in the Cyrillic alphabet, so if you don’t know how to read that alphabet (I don’t), it might be a bit of a challenge to figure out what everything is. Google Translate is helpful (I love that my phone now makes it easy to live translate what the camera is looking at).

The first BDS location I saw was absolutely packed full of local folks. I ended up going to a location closer to my hotel, and it didn’t disappoint. I had tartor, a Bulgarian chilled soup made with yogurt, cucumbers, dill, minced garlic, and walnuts. It was delicious and is probably very refreshing on a hot summer day. I also had two pork sausages, which had a different type of flavor and spice from what we typically have in the United States, and I loved it. The French fries had some paprika on them (which was fine, but not great).

I couldn’t quite finish everything, so the leftovers came back to my hotel with me. I arrived back at the hotel around 2:30 PM and I had to get to the poker tournament in time for the 4:00 PM start. Luckily, the casino is only about a 10 minute walk from the Hilton Sofia. Since I had enough time, I laid down for about a 40 minute nap. I got back up, showered, and hustled my way to the casino, sitting down just before the start at 4.

Within about the first 90 minutes, I had doubled up my stack from where I started today and felt pretty good about the direction things were going. The next hour was mostly pretty slow. Then, I got involved in a hand where I had to make a critical decision. Unfortunately, I made a mistake. It isn’t that I got unlucky or that someone else got lucky, I just literally made a mistake in how I thought through the situation and the probabilities (I won’t bore you with the details, but for those curious, the short story is that I had pocket queens and ran into pocket aces, but in hindsight I should have read the situation and known I should fold, though it’s not worth getting into the weeds here to explain why). I called when I should have folded and got knocked out of the tournament before we made it into the money. I was so bummed and frustrated with myself because it was an unforced error, but I’ll take away the memory of what I did wrong and probably make a better decision next time. In the end, I can’t complain too much: I got hours of enjoyment out of playing a big poker event like that in a foreign country. I looked at the list of entrants today, which included home countries, and I was the only American, which is an experience that I enjoy (and that always reminds me that we are our own ambassadors when we are abroad). The atmosphere and energy were well-captured in the reel I shared in last night’s update (and many of the characters in that reel were either at my table at some point yesterday or today).

After getting knocked out of the tournament, I returned to the Hilton in time to check out the evening executive lounge spread. This isn’t one to rush back to the hotel for. Yes, they had some food. And yes, they had some wine. But it was a pretty limited selection, and it was taken away around 7:30 PM. There were no desserts, which surprised me, as I feel like usually there’s an evening sweets time in a club lounge like that. Still, I wasn’t very hungry after the tournament and I had the rest of my tartor in the fridge, which I ate later on.

From there, it was back to the room to get some footage sent to Carrie so you could see what was going on these last two days on Instagram and get this journal update ready. I considered trying to go out somewhere, but it quickly got late, and the lack of sleep was catching up with me. That’s OK, I’ve had an incredible 5 nights in Europe with just 100,000 points and $1,000.

You already know that we all need to be back at our starting points by tomorrow night at 9:00 PM Eastern, so there’s no spoiler in admitting that I’m heading back to the US in the morning. Wish me luck for no delays, as I’m hoping to see you at 9:00 PM Eastern time tomorrow night.

October 6, 2025

I have dropped quite a number of clues leading up to the culmination of my trip.

From my first journal update on October 1st, I mentioned that I intended to raise the stakes, go all-in on a vacation designed around things I’ve always wanted to do, and I said that “in the end, I will be playing to win.” I was being less figurative than you may have assumed :-).

That’s because for my final stop on the 100K Vacay challenge, I am in Sofia, Bulgaria, to play in the Vamos Poker Tour event here this week! Check me out from their social feed:

 

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 I have been playing poker since I was a kid. I’ve had some success over the years with smaller tournaments, but I’ve always dreamed of playing a big multi-day tournament like the World Series of Poker or World Poker Tour. However, those events are expensive; entering one of them is a big gamble that is too rich for my blood at this point.

But then, as I was researching for this trip, I stumbled on the Vamos Poker Tour. The Vamos Poker Tour is a “mid-low stakes” poker tour that goes to numerous European cities (in 7 different countries) to host poker events with relatively high guaranteed prize pools and relatively low entry fees (at least compared to other circuits you may know — the Main Event this week, which is more expensive than the event I am playing, has a guaranteed prize pool of 200,000 Euros, but it only costs 350 Euros to enter. Compare that to WSOP or WPT events, which often feature buy-ins of $1,500 to $10,000).

Even more interesting, in my opinion, is that the Vamos Poker Tour visits quite a number of reasonably priced European cities in terms of the cost of visiting them. Sofia, Bulgaria, is a great example! The average restaurant meal here costs something like $12, public transit costs a maximum of $2.39 a day as long as you use the same tap to pay card every time (it won’t keep charging you once you reach the daily max — then it’s just free to ride!), and the Hilton Sofia, which had a nightly rate of $303.53 per night for the two nights I booked at the time I booked them (and which sold out entirely weeks ago!) only costs 40,000 Hilton Honors points per night (16,000 Amex points per night). Interestingly, Hilton Gold members and higher get free restaurant breakfast and Executive Lounge access here! While Executive Lounge access is ordinarily only guaranteed for Diamond members and is ordinarily only available to Gold members if they are upgraded to the Executive Floor, I confirmed at the desk that what I had heard was correct — Gold members get lounge access here!

But let me back up a few steps, because there is a lot more to the story.

You know how I told you yesterday that I watched the James Bond movie Casino Royale to prepare for my next destination? I made it sound like that was all about Belgrade and the Saint Ten Hotel. Indeed the spy upon which the Casino Royale story was based was known to stay there and attend social events at the Saint Ten Hotel, so the movie and hotel did align well, as you can read about in yesterday’s journal post below. However, I told you a half-truth….

You see, Belgrade was actually a layover on my airline ticket I had. The final destination of that ticket was Sofia.

That’s a part of the story that I want to explain. When I found this poker event that I wanted to attend, I started looking up flights from Malaga, Spain to Sofia. As is customary for me, I started at Google Flights, running a one-way flight search.

When I did that, the cheapest flight from Malaga to Sofia was on Air Serbia. However, it was not a pleasant-looking itinerary. I didn’t actually take a screenshot of it on Google Flights, but here’s a screenshot from the Air Serbia site of the only flight option that Google Flights showed for a one-way search.

That itinerary would have looked something like this:

• Depart Malaga at 12:50pm, arrive in Belgrade 4:10pm
• Depart Belgrade 12:55am, arrive in Sofia 2:55am

That sounded awful! I wouldn’t really have the time to do much in Belgrade, and I guess I’d have to book my hotel in Sofia for the night before in order to have a room when I arrived at 3am. And the hotel was about a 35-40min public transit route from the airport. No thanks.

But it dawned on me that Air Serbia must also have a daytime flight to Sofia. I went back to Google Flights and instead of choosing “one-way” for the search type, I chose multi-city. I selected Malaga to Belgrade on Sunday, October 5th, and then Belgrade to Sofia on Monday, October 6th.

That itinerary would give me a full night in Belgrade (about 21 hours on the ground!) and still get me to Sofia in time to play cards. Even better, it was exactly the same price as the awful itinerary.

This isn’t the first time I’ve ever noticed this, but I kind of forgot about it. I thought it was very much worth highlighting this because in many cases, you may have additional itinerary options beyond the initial Google Flight search results. When you run into an itinerary that has a layover you don’t like, trying the multi-city tool might be well worth a few extra seconds of searching. Note that this can also sometimes work with flight award searches.

In this case, at about $111, it was a much better deal to book this as a paid ticket than an award ticket. I often find that’s the case within Europe. Rather than hunt out an exception where flights were more expensive just to say that I got more value for my points, I thought it was worth highlighting how you might be able to get a better flight with cash by using the multi-city search function.

Now let’s get back to James Bond.

If you haven’t watched the movie Casino Royale, the gist of the plot is that James Bond gets involved in a high-stakes poker game with a villain. It’s a winner-take-all poker tournament with a $10 million buy-in and one $5 million rebuy if you lose your first $10 million. Things don’t quite go according to plan for Bond on that first buy-in, and he loses the $10 million. The British government won’t stake him for the additional $5 million, so it seems like hope is lost. Then, the CIA steps in and stakes him for the final five million, and he comes back to win it all.

Here, I found myself in a very Bond-like scenario.

You see, I had the budget for this trip laid out in its entirety, and it was going to fit in under budget, but the cash was a little tight. Then, my Iberia flight from Boston to Madrid on the very first day was delayed, and I missed the separate ticket I had purchased from Madrid to Malaga. I had to scramble for a solution and ended up with an Air Europa award, adjusting one of my Hilton stays to use cash in points to free up space in the points budget for the Air Europa flight. But that meant spending money that I hadn’t intended to spend. There were also a couple of other expenses along the way that added relatively minor amounts, but combined with that emergency save on the missed flight, I no longer had space in my budget for the poker tournament. Before arriving at the Palms Royale Casino for the poker tournament (it’s not Casino Royale, but how fitting is it that it still has those words in the name!), I only had about $160 left in the budget for both the tournament and food in Sofia, but the tournament entry was about $200. Buying in with that $200 would have busted the budget!

But just like James Bond in Casino Royale, I didn’t want to give up on my dream of poker glory.

So I decided to take $100 into the casino to play a cash game (of the $160 I had left). The tournament offered late registration all day today, so if I could double my money before registration ended, I would play the tournament, having only risked $100. If I lost the $100, I wouldn’t be able to play the tournament and would use my remaining $60 to have a great time in Sofia. I don’t really think of the $100 ventured there as being used to expand the budget but rather, just the same as I had originally budgeted for $200 out the door for the cost of entering the tournament (and I wouldn’t wipe away all the money I’ve previously spent even if I won $1,000 in the tournament), in this case I re-budgeted only $100 and decided to get as much entertainment out of that $100 as possible.

I am happy to report that I was able to get myself into the tournament pretty early in the game! The tournament started around 6pm local, and I was in it before 7pm.

This is a 2-day tournament, so play today ran from the start around 6pm until 2:30am local time. Those still standing at 2:30am would return for Day 2 tomorrow at 4pm local time to play out the rest of the tournament.

At 2:30am, I was still alive! Out of 175 entrants, 66 remained when we paused for the night, including yours truly. I am far from being the chip leader, but I am still very much in the hunt. The highlight of my night was probably flopping four of a kind with a pocket pair and the other two on the board — and managing to end up with all of my chips in the pot with a caller. The poker enthusiasts out there will get that!

While I know that many readers probably aren’t poker players, I can’t tell you how enjoyable this has been for me. First of all, I love to play poker. I find poker to be incredibly relaxing. When you’re playing well, you’re probably only getting involved in 2 or 3 big hands per hour, mostly otherwise folding like it’s laundry day. So, for me, there becomes a zen-like quality of sitting at the table for hours, just people-watching and zoning out. I compare it to distance running in that you can kind of empty your mind and truly relax. I love it, but I rarely get to do it. I have played a tournament once or twice during family trips to Vegas, but I always feel bad about ditching the family to sit at a poker table for hours. It doesn’t have the same relaxing quality as being able to just sit and play, with nobody waiting on you to be done, and without feeling like you’re missing something else. You may rather relax at a spa or with a good book; poker is like my spa or reading time.

At the same time, poker is highly social. The vast majority of players in this tournament are from Bulgaria or Spain. I didn’t notice any other Americans in the room. While the official casino languages are Bulgarian and English, almost all poker action was announced in English and I think everyone at the table spoke English well. The guy sitting across from me struck up conversation about his wife having an upcoming trip to New York and about life in the US and places to visit in Bulgaria and about some backpackers from the US that he met and invited to stay with him years ago. It was a lot of fun!

And I love how Texas Hold ’em has become such an international game. I chuckled to myself about the fact that we were in Eastern Europe playing the Texas variant of a card game. I have enjoyed the chance to play overseas in a number of places, including in Macao, China; Osaka, Japan; San Jose, Costa Rica; and I believe I also played in Quito, Ecuador. But, until this trip, I don’t believe that I’ve played in Europe, despite poker being really popular in Europe.

I should also mention that I saved money on food tonight: poker tournament players enjoyed a free buffet dinner in the casino during a 45-minute meal break (and I got a ticket for a free buffet dinner for tomorrow night as well). I’m not sure if that’s something common; I had somehow missed getting a ticket for that, and when I asked about it at the buffet, they insisted I just eat and worry about it later. I wasn’t sure if players had to buy tickets or were given them with registration. When I asked about it later in the poker room, they apologized that I hadn’t gotten a ticket and gave me a ticket for a free buffet tomorrow. The food was actually delicious!

Don’t worry, I’ll get some local food outside of the casino tomorrow. Speaking of that, I do have daytime plans since I don’t need to be back to the casino until 4pm. I am very excited to get not just one but two nights of poker on this trip, but I am just as excited to see Sofia tomorrow! The weather doesn’t look great, but I look forward to making the best of it nonetheless.

But, as I wrap this up, it is already past 5:30am local time, so I need to get a few hours of sleep and breakfast so I can tackle the rest of the day and then hope to end up in the money at the Vamos Poker Tour event! Wish me luck.

October 5, 2025

I dropped a few hints about my next destination, but I’m betting that nobody put it all together.

In my October 1st journal entry, I noted that I wanted to have some surprises and remain a man of mystery. Then, last night, I mentioned that I was watching a movie starring Daniel Craig to prepare for my next destination. What international man of mystery did Daniel Craig play? The name is Bond, James Bond.

To understand what that has to do with my destination, you need some back story about the James Bond character. Ian Fleming wrote the James Bond story, reportedly loosely based on himself and several other spies he worked with in his days as a British MI6 agent. One of those agents who is largely believed to be one of the main inspirations for the James Bond character was a man named Dusko Popov. Popov was a triple agent who worked for the Yugoslav intelligence service, Germany, and the British MI6. During World War II, he was tasked with feeding disinformation to the Germans that led them to believe that the Allied invasion would come at Calais, not Normandy. The Germans bought into that, which was caught in the code breaking that happened at Bletchley Park (and that code breaking team was the inspiration for the movie The Imitation Game, which is not the movie I watched last night).

Popov was said to have had very James Bond-like characteristics in that he was known to romance many women and hobnob with high society. He was also known to be quite a gambler. In fact, at one point, Popov and Ian Fleming were both stationed in Portugal and both ended up at a casino there together. Popov apparently got into a wild game and made a bluff of something like fifty thousand dollars (keep in mind that this was in the early 1940s!), which apparently was the direct inspiration for the first James Bond story, Casino Royale (which is the movie I watched!). In fact, some claims I’ve read indicate that the story very closely parallels what actually happened.

Popov came from a wealthy Serbian family. When he was in Belgrade, he was known to stay at the Saint Ten Hotel, which was designed by a famous Belgrade architect whose family was prominent in politics and business, and the hotel was a location known to host MI6 agents as well as many diplomats and wealthy and powerful folks. The Saint Ten Hotel, located in the famed Vračar district of Belgrade, was renovated and reopened as a Small Luxury Hotels of the World property in 2017. Tonight, I get to live the life of an international man of mystery thanks to Hilton Honors points!

At 50,000 Hilton Honors points per night, this property only presented slightly better than reasonable redemption value for Hilton points. In an interesting case, the cash rate was cheaper for one person than for two people. If we base the point value on the rate for 1 guest, it only presents around 1.25 cents per Amex point, but if we base it on the value with two guests in the room, it bumps it to more than 1.6 cents per point. I used 43,000 Hilton Honors points (17,000 Amex Membership Rewards points, thanks to the 25% transfer bonus, making the ratio 1:2.5) and about €35 (less than $42) as a cash and points stay to stretch my Points a little bit further while using another quarterly Hilton Credit to pay the cash portion of the bill.

But my motivation here to visit Belgrade went well beyond the ability to stay in a hotel once frequented by the real-life James Bond.

Before Frequent Miler, I worked remotely for a company based in Asia. Years ago, they flew a bunch of us who worked remotely to Shanghai for an important event. At that event, I met a guy named NiKola. At first, I thought Nikola was American because his accent sounded perfectly American. However, I soon came to learn that Nikola was from Serbia.

In talking with him over the course of the week that we spent together in a large group, I quickly realized that not only did I know very little about Serbia, but having grown up in the 90s and having learned most of what I knew about Serbia from television news, I had a mental image of Serbia that didn’t necessarily match modern life there. To me, that’s such a big part of what travel is about: recognizing and challenging the preconceived notions that you didn’t even realize you had until they were challenged. That type of cultural exchange really excites me.

Ever since meeting Nikola, I have wanted to visit Serbia one day. In fact, when I began planning my 3 cards 3 continents trip in 2022, I fully intended to fly Air Serbia for the first leg of that trip (rather than the Egyptair leg I ended up flying). I had even reached out to Nikola to make sure he would be available. In the end, I couldn’t make that work with the other flights I needed, so I had to abandon that plan. However, I have wanted to see Belgrade and hang out with Nikola here ever since meeting him, so when I saw the opportunity to get here on this trip, I immediately reached out and Nikola was gracious enough to show me around his city, tell me all about its history, and spend hours discussing everything from history to politics to parenthood to life in a big city versus a small town, all through the lens of life here versus in the States. It was a terrific evening; it reminded me very much of the dinner we enjoyed in Buenos Aires on our Party of Five challenge, only in this case I was already familiar with Nikola.

And the food! Nikola took me to a place called Velika Skadarlija restaurant, which he said was super authentic and traditional (and delicious!). He wasn’t lying! We shared the “Saber of a Hero” dinner, which actually serves 4 people and is literally served on a sword. The waiter removed the meat from the sword upon which it was skewered (you’ll have to keep your eye on Instagram for a video of that).

The dinner was terrific. Service was wonderful, there was live traditional music, and the meats were incredibly tasty.

We had a great time walking around Belgrade at night. I never would have had the same experience on my own as I had hanging out with Nikola. His kids are exactly the same ages as my own, so I’ll have to get the rest of the family here to hang out one of these days. In the meantime, this was a terrific stop. More on how I got here tomorrow, as I raise the stakes with a final twist.

October 4, 2025

Back in 2008-2009, in what feels like a previous lifetime, my wife and I spent about 9 months in Ecuador. At the end of our time there, we spent most of our last couple of weeks in what is (or at least at the time was) a sleepy little coastal town called Canoa. I think a private room in a hostel cost us something like $7 or $8 a night, and we spent our days sipping on fresh batidos (fruit smoothies) and hanging out around a bar and grill called the Surf Shack.

The Surf Shack got its name because Canoa was famed for its easygoing surf. Known as a great place to learn (or to have some low-intensity fun for those more experienced), there is no doubt that surfing was the primary activity in Canoa.

Having grown up nowhere near the beach, I had the Hollywood image of surfers/surfing being the coolest thing ever. It looked like so much fun gliding around on the waves on a surfboard. I couldn’t wait to try it for myself!

So my wife and I signed up for a beginner surfing lesson and got out in the waves with a longboard. We spent what felt like all day in the water. I was awful at surfing. It turns out that Hollywood surfers look like they are chiseled from rock because it requires way more upper body, lower body, and core strength than I’d have ever imagined to get your legs under you and stand on the board. Even when I got on the board, I would sometimes get my weight a little too close to the front of the board, sending the front end into the surf. As you might be able to imagine, that effectively turns the board into a giant catapult — I got slammed face-first into the water more times than I could count.

But then I got up on the board and surfed — and it was everything I imagined it to be. Those who snowboard surely understand the feeling of gliding along on the board. It hasn’t been in the cards to do it again in the many years since, but I have always said that I would gladly get slammed into the water again and again for that handful of times I got up on the board and rode a wave in. When we travel to places like Hawaii or the California coast, I love watching the surfers do their thing, thinking to myself, “in another life!“.

I don’t quite remember the first time that I saw someone windsurfing, but I was immediately even more enamored with the idea of it than I had been with surfing. After all, it looks like you get the best part of surfing — gliding around on the waves — but because it is wind-powered, you can (theoretically) stay on the board for far, far longer.

On a cruise this past winter, we saw hundreds of windsurfers in Bonaire, zipping back and forth across the water for what felt like forever. It looked like so much fun! I made my wife promise me that we’d go back someday, maybe when the kids are a little older, to learn how to do it.

So when I began turning the focus of my 100K Vacay trip to things I have always wanted to do, the literal first thing that came to mind was windsurfing. I mentioned in a post last week that I really wanted to make the Canary Islands work for this trip, but couldn’t. One of the reasons was for the windsurfing! But then I found Malaga and discovered that it is also a popular spot for surfing, windsurfing, kite surfing, and hydrofoil. I knew I had to figure out a way to make it happen!

Many of the area’s surfing schools run multi-day courses and camps to learn how to windurf/kite surf/etc. That sounded great, but I didn’t necessarily have the budget to do a multi-day course along with everything else I have planned. But I found a company called Dynamic Windsurfing offering a Beginner Day 1 course.

Dynamic Windsurfing is actually a company based in Scandinavia that makes unique and adjustable windsurfing equipment that is made to be able to adapt as your skill increases. It seemed like a great way to learn!

I initially found Dynamic Windsurfing through third-party booking sites like Viator, Klook, and GetYour Guide. I did check their website directly, but, surprisingly, the price to book directly through their site was exactly the same as the price through the third-party booking services. I still might have considered booking direct under ordinary circumstances, but one of the criteria of this trip is affordability. Booking through a third-party OTA would give me the chance to stack with some shopping portal cash back.

However, somewhat oddly, the class scheduled for today (Saturday, October 4th), was not available through sites like Viator and TripAdvisor (other days of the week were, but not Saturday). The good news is that Saturday was available through GetYourGuide.com. While portal rates weren’t quite as good for GetYourGuide, I figured that I might be able to get a targeted offer from Capital One Shopping by clicking around on the GetYourGuide site in the browser where I have the Capital One Shopping extension installed. Sure enough, less than a day after clicking around, I got a targeted offer for 9% back via GetYourGuide.

That wasn’t a huge win here since the Beginner Day1 windsurfing class was only about $88.63. Nonetheless, I was able to get about $8 back in Capital One Shopping Rewards. A win is a win, and I am playing to win!

However, while the windsurfing is in Malaga province, it isn’t in Malaga proper. Google Maps put the meetup point at around 1 hour by car from downtown Malaga. I had originally considered renting a car, but then I found a public transit path mixing a local train and local bus service, so I planned on taking the train and bus combination for the fun of figuring it all out, despite the fact that it would take twice as long.

However, I made the mistake of not writing down the details. Last night, before going to sleep, I went to look up those details so I could know what time I needed to be at the train station. Suddenly, I couldn’t find any public transit method to get to where I needed to end up. I spent well over an hour searching last night (from about 2-3 o’clock in the morning!) and couldn’t find whatever I had previously found.

That left me scrambling for other ways to get to the meetup point. I tried rental cars through Autoslash, but prices started around $47 for the day. I next tried Kayak, Rentalcars.com, and Klook car rentals. Klook had a company called Click2Rent listed at about $32 for the day. Reviews for Click2Rent were mixed (either saying the experience was great or that it was all high pressure to buy their insurance package or get hit up for damage charges later).

While evaluating, I decided to check Click2Rent’s website. I was surprised to find that they offered an “economy” booking option (which included no insurance and only 250km per day) for only 21 Euros!

That was only a couple Euros more than I had expected to spend on public transit, so I decided to go ahead and book it.

Picking up the car was a little slow. I did the online check-in, but perhaps there wasn’t enough time between when I did it and when I showed up for the later later the same day for it to get processed. I had to take a number and wait. Luckily, it only took 10 or 15 minutes for my number to be called. Unfortunately, the car wasn’t ready. Still, they got the check in process complete and told me they’d have the keys within 15 minutes. When I got back to the waiting room, but stomach sank a little bit as the place had suddenly been slammed with customers. I’m really glad I wasn’t at the back of that line. There must have been at least 30 or 40 people in the waiting room (versus 2 when I arrived). True to their word, I had the keys 15 minutes later.

I then drove to Atalaya Isdabe for the meetup point, parking for free on the street. I did have to pay tolls in both directions (5.50 Eur both ways), but having my own car meant that I could pick up a Too Good to Go order from a bakery and stop at the mall to chill out / rejuvenate after windsurfing (which I needed). More on that in a second.

Windsurfing was a lot of fun. This ended up being a private lesson, so it was just the instructor and me. He went through a brief explanation on land (only about 10 minutes) and then helped me get the board in the water and coached me from the land. I was a little nervous being in the water by myself (what happens if you catch a good wind and end up much farther out than you anticipated, and you can’t get back??). But that faded when I got on the board and started sailing.

I’ll note that the wind wasn’t very strong, and I think that was really helpful. And I still fell off the board plenty of times. Perhaps most surprising to me was the strength required. I anticipated that I wasn’t in good enough shape to do this well, so I started biking 5-8 miles almost every day about 5 or 6 weeks ago (I really wanted to do this!!). I’m glad I did that much, because after less than 2 hours on the board, my legs were toasted and I had increasing difficulty getting my balance. The guide told me that this is very normal for beginners. I can see now why most make this a multi-day course. If I had the time, I’d definitely try again, but I’d also start preparing sooner (I intend to keep up the cycling when I get home).

I wore an Insta360 camera on a chest harness to get footage of this activity (and my falls off the board). I didn’t have any other way to capture images of it in the moment, so you’ll have to check out the reel on Instagram to see it.

 

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Back to my DIY picnic: Too Good to Go is an app I’ve talked about before that saves food waste. While I originally wrote about it in the context of using it in the US, during Million Mile Madness, I noted that I’d discovered that it is a European app and is much more widely available in Europe. I love the adventure of only paying a few bucks and getting what you get! It’s kind of like the knock-off version of a tasting menu :-). I paid 5 Euros and got a huge loaf of some sort of multi-grain, four small sourdough rounds, and 3 chocolate-filled pastries. The bakery’s website notes (you’ll have to use a translator as I have to get the English below):

All our breads and pastries are naturally fermented using our sourdough starter, Juliette. It’s ten years old and has been tested in several of Europe’s finest restaurants. By naturally fermenting, our products are incredibly tasty, longer -lasting, and nourishing for the body and mind. These are breads that will change our lives and care for our planet.

In order to fully enjoy as much of the bread as possible, I stopped at a grocery store (inside the shopping mall!) and bought some Spanish cheese (Queso Iberico Tierno is what the label says) and a bottle of wine — Riva Rey Rioja, which spoke to me. The wine and cheese combined came to about 5.70 Eur (I also bought a 5L bottle of water — I was very thirsty — for about 0.92 Eur). The wine was 3 Euro for the bottle. No, I didn’t drink the whole bottle; I just couldn’t resist the opportunity to make my own little picnic dinner for a very reasonable price.

Along with my little picnic was a planned moment of relaxation. I love the sunshine and heat of Malaga as much as anyone, and I made a good effort to take advantage of that with outdoor activities. But after an overnight flight from the US and hustling to the activities I’ve done, I was ready to kick back and relax tonight. One thing I love to do to relax, but haven’t done much at all since having kids, is watch a movie (my kids haven’t been into movies, and I just don’t dedicate the time to it despite enjoying them!). So for this trip, I downloaded a movie starring Daniel Craig that I planned to watch tonight. I specifically planned to watch this specific movie at this point in my trip to prepare for what is yet to come.

October 3, 2025

Everybody who knows me knows that I love

1. Sand between my toes
2. Sunshine overhead

For my first stop on this 100K Vacay, I couldn’t wait to land on the Costa del Sol at Malaga, Spain.

This morning, I first landed in Madrid, Spain on an award I booked using Iberia Plus Avios. Just last month, I covered an incredible award sale using Iberia Avios. While I had initially planned to get to Europe using 6,000 Virgin Atlantic points and about $110, I couldn’t turn down the chance to fly from Boston to Madrid for just 6,400 Avios and about $90. I had to book it, particularly given the fact that our planning window had included a 30% transfer bonus to Avios. We had decided in the rules that any transfer bonus occurring during our planning window was fair game for the purposes of accounting for our points. That meant that this flight would only cost me about 5,000 Membership Rewards points.

I have long been an advocate of striking while the iron is hot. That is to say that my advice has long been that when you see a hot deal, you should take advantage of it without hesitation or delay. I knew that I would take a hit on “applicability” given the fact that this was an award sale rather than a regularly-priced award. I can live with that better than I could have lived with not taking my own advice to strike while the iron is hot. I slammed down the Avios for that flight with enthusiasm.

Yes, I flew economy class on Iberia. Yes, it was awful.

It wasn’t supposed to be quite so bad. I had been able to select a free “up front” seat (as in “at the front of economy class”, not “up front” as in business class) at the time of booking, so I had selected an aisle seat near the front of the plane. Unfortunately, I woke up early in the morning on the day of departure to an email indicating an equipment swap was incoming.

Not only had my seat been changed, but I had been given what is arguably the worst seat on the plane.

We had originally been scheduled to fly on a widebody A330 (a plane with two aisles). Two days before departure, the middle seat in my row was still empty (as were many other seats on the plane). Sadly, on the day of departure, they swapped in an A321XLR. That is a single-aisle plane.

I went from an aisle seat on the A330 to a window seat on the A321. And it wasn’t just any window seat — it was the window seat directly in front of the emergency exit row. If you’ve ever been unfortunate enough to get that row, you’ll know that the seats in front of the emergency exit row do not recline. Not only was I stuck flying economy on a narrow-body plane, but I was jammed into a window seat that didn’t recline for an “overnight” flight (originally scheduled to depart at 4:35pm, though that was delayed). While the vast majority of my international travel is ordinarily in business class thanks to miles and points, we flew plenty of economy class during last year’s Million Mile Madness. I haven’t been in a seat that felt more cramped than Iberia’s A321 XLR seats. Think approximately the legroom you get on Spirit Airlines, but for a much longer flight. I had very, very little room to move or maneuver when I wanted to get things from my bag or put them back in. The price was terrific and I’m glad to have gotten to Europe for less than the cost of an average domestic US flight, but I really wish it had been on the originally-scheduled equipment. That was some bad luck!

I will say that the in-flight entertainment screen was large and looked very nice. And, in a really fun twist, it had Where in the World is Carmen Sandiego? I loved this game as a kid and had a blast playing a round!

We landed in Madrid early this morning, but I didn’t really want to go to Madrid. Málaga, on the other hand, still enjoys daily highs in the 80s (in degrees Fahrenheit) at this time of year. In fact, today was a high of 81° and tomorrow is set to reach 86° — perfect beach weather! I caught a flight this morning from Madrid to Málaga (more details on that to come tomorrow).

But I’m not here just for the beach. I’m in Malaga because it is going to afford me the opportunity to do three things that I have always wanted to do.

By the time this post publishes, I’ll have done the first, but in order to fully appreciate it, let me add some context. My last name, Reyes, is Spanish. It is the plural form of “rey”. Do you know what “rey” means in Spanish? It means King. A family member who did some research into the family lineage and history once told us that the origin of the name came from theater performances in Spain long, long ago. The story goes that the folks who played the kings in these early theater productions all came from the same family, so the family that produced the kings became known as the Reyes family. I’ve always been a bit dubious as to the details of the story, but that is the story, and I am sticking to it.

How fitting it is then that this Reyes has gone back to my Spanish roots to play King of the 100K Vacay.

My father was born in Puerto Rico, but his family moved to New York City when he was just four years old. His parents, my grandparents, continued to live in New York City into my early teenage years, so I made numerous visits to my grandparents’ apartment in Washington Heights in the early 80s.

My dad always loved showing me and my sister the city, so we did the touristy things multiple times. As a kid, I climbed the steps to the crown of the Statue of Liberty and took the elevators to the top of both the Empire State Building and the World Trade Center. As far back as I can remember, I was terrified of heights.

In fact, without having seen a picture of it in a couple of decades, I distinctly remember the upper floors of the World Trade Center. There were floor-to-ceiling windows with sort of mesh metal benches in front of them. The benches were bolted to the floor even though this was the part of the building where you stood inside (as I recall, visitors also walked outside on the roof of the building, but the benches by the windows are the memory that stuck). This is a picture of my sister and me standing next to one of those benches.

The reason I remembered the benches so clearly is that I couldn’t take my hand off one. I very clearly remember feeling safe as long as I was holding something bolted to the floor, but I couldn’t stand and look out the window without holding on. I knew that my fear was completely irrational as we were inside the building, but I couldn’t control it. That photo is probably more than 30 years old, and I still remember the experience vividly.

Interestingly, both the fear of heights and the sense of safety when strapped in have stuck with me. Airplanes and roller coasters don’t bother me, I think because I am strapped in securely. But about 15 or 16 years ago, my wife and I hiked Huayna Picchu, the peak behind Machu Picchu. The path is a stone staircase, but I couldn’t descend that staircase on foot thanks to my paralyzing fear of heights. Instead, I sat on my butt and slid down the entire staircase, one step at a time. My wife took a photo to commemorate the occasion.

Again, I know that my fear of heights is totally irrational. And I hate that it has held me back from some things over the years. There’s a hike not terribly far from where we live with a steep cliff. My wife has to be the one to take the kids to the edge to look out — I can’t even watch.

But I’d like to change that. I don’t want to be afraid of heights. So today, here in Malaga, this king attempted to conquer my fear of heights — and what better place to do it than Caminito del Rey, a hike that was long considered one of the most dangerous in the world and which takes its name from a Spanish King who himself crossed this perilous path back in 1921? Today, I walk in the footsteps of Reyes past.

After donning my crown (the helmet!), conquering my fear of heights, and walking in the footsteps of an actual Spanish King, I was admittedly worn out. The hike is a little over 3 miles plus an additional mile hike to the entrance point. I was ready to get some sleep!

But I wouldn’t be very true to my Spanish roots if this King didn’t sleep in a Palace, so my first stop in Malaga was to get my key to the castle here at Palacio Solecio, a Small Luxury Hotels of the World property bookable with Hilton Honors points. Staying in this Palacio tonight would have cost more than $500 in cash, but I am using 60,000 Hilton Honors points, which I got by transferring 24,000 Amex Membership Rewards points with a transfer bonus, yielding a net value of more than 2 cents per Amex point! I think I’ll sleep soundly here tonight.

 

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Palacio Solecio markets itself as an 18th century Andalusian palace-turned-hotel. Service seemed terrific as an employee showed me around and explained some of the history of the hotel, including the fact that Pablo Picasso was baptised at the church directly across the street (this hotel is actually in the historic, pedestrian-only center). Pablo Picasso was born nearby here in Malaga and lived in this neighborhood as a kid.

Now, off to get a few hours of shut-eye before I move on to the next thing I’ve always wanted to do. See the last full paragraph of the October 1st entry below for the hints I’ve dropped if you’d like to figure out what could be coming next.

October 2, 2025

As this update publishes, I’m shipping up to Boston!

I intentionally chose Boston to kick off our 100K Vacay challenge. Despite living in upstate New York (which, for those unfamiliar, has a distinctly separate identity from New York City, I consider myself a New Yorker, through-and-through. My father grew up in New York City and we used to make the long drive several times a year to visit my grandparents’ apartment in Washington Heights (Manhattan) in the early 80s.

Why, then, did I choose to leave from Boston, arch-nemesis of New York?

The answer is JetBlue (and not JetBlue).

Despite the fact that we live about equally distant from Boston and New York’s JFK airports, Boston has typically been a second, third, or ninth thought for me in award searches. In fact, I have probably more often searched awards departing from Washington-Dulles (IAD), which would require a flight to reach, than from Boston, which is far more convenient to reach.

That’s probably a subconscious result of the Boston-vs-New York rivalry. However, during our summer JetBlue travels in pursuit of the 25 for 25 promotion, we passed through Boston numerous times. In those trips through Boston, I came to really appreciate the Boston Sapphire lounge, to which I have access thanks to my Chase Ritz-Carlton cards. The food is good, the service is friendly, and the lounge is comfortable.

Even better, the lounge can be accessed by anything flying out of terminals B, C, or E since they are all connected airside. In other words, you can be flying almost any airline at Boston Logan and have access to the Sapphire lounge. I loved that. One of the things I hate about JFK airport is that the terminals are not connected airside. I always end up booking a flight that fits my needs only to find that I don’t have the lounge option I want. I was glad to depart from Boston this time around in order to have access to the Sapphire Lounge regardless of which airline I was flying (note though that Delta uses Terminal A for some flights, which is not connected airside).

Sadly, my morning didn’t go quite as planned. I had built in plenty of time to get to Boston Logan comfortably ahead of my flight, but some things (unrelated to the challenge) slowed me down and I didn’t get to the airport as early as I expected. That could have been a problem since I hadn’t yet eaten anything today. However, I had a backup plan: U.S. Bank Priority Pass cards still offer restaurant access, which provides for $28 (or local equivalent) off of the bill. Since this is a discount rather than a rebate, we had discussed ahead of time that it would be fair game. And, thankfully, Boston Logan’s Terminal E has Stephanie’s, which takes Priority Pass.

I ordered a delicious hummus plate and a coca-cola, which came to $28.36. Perfection!

In a little while, I will board my first flight of the 100K Vacay challenge. This time around, things will be less about the journey and more about the destinatinon(s?). Stay tuned tomorrow for more on that . . . .

October 1, 2025

Ultimately, I decided that for this trip, I’m going full vacay mode, and it’s all about me. Nothing says “living-the-dream vacation” like planning an entire trip centered around doing things you have always wanted to do, but have never done before. The point of my trip isn’t to impress you with flashy style (though I do have some of that up my sleeve!), but rather to inspire you to get out there and live the dream the way that miles and points can uniquely make possible by creating the opportunity to go places and do things and indulge in those vacation dreams of your own.

Will a trip designed around my interests match your interests? The answer to that is probably going to be “yes” in some ways and “no” in others, but know this much: I intend to take things to new heights and harness the winds of opportunity as I conquer the road that lies ahead. In the end, I will be playing to win. Though that may give you some hints, expect some unexpected twists as I try to live the life of a man of mystery. Make sure to also follow Frequent Miler on Instagram (@Frequent_Miler) as that format is much better suited to sharing the travel story in near real-time.

For more on what drove me to this focus, see: Getting ready for full vacay mode: Nick’s 100K Vacay focus.

Why I chose Amex Membership Rewards points

I love Amex points because they are relatively easy to accumulate

In recent years, we have frequently referred to the Amex points parade, which has marched on and on with numerous opportunities to earn big welcome bonuses, authorized user bonuses, and more. Beyond that, it is possible to earn American Express Membership Rewards points through shopping portal Rakuten as well as via some very useful bonus categories on several Amex cards. Cumulatively, it all adds up to Amex points being easier to accumulate en masse than other transferable currencies. That alone makes whatever I do for the challenge pretty widely applicable in the sense that there are so many ways to earn 100,000 of my points.

All that said, in this case, while I expect the ease of accumulation to help me in terms of applicability, it is otherwise of no use to me. I can’t get more points for this challenge. I need to work within an artificial budget, but I love that it is one so easily accessible.

Amex has great airline partners

I know what you’re thinking: this is a competition that you expect to be about lodging. But I don’t think that needs to be as focal a point as Greg made it sound in his announcement post. After all, I still wanna get away. I love using these challenges as an excuse to get to some far-flung destination that might not have ever otherwise been on my radar and to show how easily it can be done. During 40K to Far Away, I ended up in Niue and joined the yacht club; in 3 Cards 3 Continents I ended up in the Arctic Circle in Finland to visit Santa and see the Northern Lights after snorkeling with whale sharks in Oman (and more). To me, an exciting vacation for one (just me) takes me somewhere I may not have considered were it not for miles and points.

And the good news is that Amex has the hands-down best set of airline transfer partners. They have almost every good partner that anyone else can access — and more. That gives me a multitude of ways to get away.

I typically love the combination of the relative ease of Amex points accumulation and its wide range of airline partners because that often makes it possible for me to make great use of partnerships for business class award tickets. In this case, since we are limited to 100K points, it feels like I will likely be limited to traveling in economy class, particularly if I want to go far.

The good news is that I think it is possible to get farther from home than many think despite the budgetary limitations.

Amex isn’t actually as weak for lodging as you think they are

Another reason I wanted Amex here is because a lot of people believe that Amex doesn’t offer good opportunities to use points for lodging. And that’s not as true as some think it is. I can’t wait to show just how well you can do.

In fact, I think many would be surprised at how much value can be had at the lower end of the spectrum with both Hilton and Marriott. While Hyatt certainly dominates the mid-tier hotel market and has much lower award pricing at the top end than competitors do, the disparity at the bottom end isn’t as big as it sounds. Sure, Greg could get a Category 1 Hyatt for as few as 3,500 points per night…..but I doubt he will! I don’t think Greg is very likely to stay at a Category 1 Hyatt and he is even less likely to do it during off-peak dates. I think it is far more likely that Greg will spend 8,000 to 12,000 points per night on lodging. Given the Amex-to-Hilton transfer ratio of 1:2, transferring 8K to 12K Amex points to Hilton would give me a budget of 16K to 24K per night with Hilton. While there aren’t necessarily tons of great properties in that pricing band, options do exist — even before accounting for something like a 5th night free redemption.

Furthermore, you can’t count out Marriott. While I typically advise strongly against transferring Amex points to Marriott, the fact is that there are at least some properties priced around 12.5K points per night that offer more than 1c per point in value.

Transfer bonuses are common

Another thing to absolutely love about this competition is that Amex frequently offers transfer bonuses, and they are often among the most generous in the industry outside of Bilt. I expect to see monthly transfer bonuses between now and when the competition kicks off. In fact, for the past two Septembers, Amex has launched around a dozen transfer bonuses near the beginning of September. That could make things tight in terms of transferring and booking if I waited for early September bonuses, but nonetheless, there are likely to be at least a few great transfer bonus opportunities between now and “go” time.

The frequency of Amex transfer bonuses make them a superpower of this particular currency. I feel like I need to leverage at least one good transfer bonus.

My strategy

As I said above, I feel like the applicability of my strategy should naturally be high given the fact that I have what I feel is the easiest currency in which to earn 100,000 points.

However, Amex has some unique transfer partners that could give me a distinct advantage over my competitors. Nobody else could leverage ANA for round-the-world flights to connect multiple destinations, and one-way awards will soon make it possible to get some terrific deals on long-haul flights. Further, I am the only competitor who can transfer to Hilton Honors and I think it would be really fun to demonstrate great value from a transfer to Hilton for a lower-tier property, perhaps in a really interesting destination.

On the one hand, it makes the most sense to leverage those partners that make Amex Membership Rewards points stand apart from competitors. Wouldn’t it be great if I could demonstrate an outstanding vacation using Delta and Hilton?

On the other hand, wouldn’t it be neat if I beat everybody else by using partners that they all could have accessed? Wouldn’t that both demonstrate the strength of Membership Rewards as a currency and an above-average skill in using points and miles?

We have many partners that we all share: Avios, Air France / KLM Flying Blue, Emirates Skywards, JetBlue TrueBlue, Singapore Krisflyer, and Virgin Atlantic Flying Club are the notable examples.

To be clear, beating everyone with points that they could all access would be really, really hard from a lodging standpoint. In fact, it may not be possible at all. While Greg & I share Marriott and Stephen, Tim and I share Choice Privileges, there are no universal hotel partners. And we agreed that hotels need to be booked with points (or perhaps cash & points in the right scenario), not cash. I may not end up with a choice here: I may need to stick with beating their flights with points they could have (or arguably should have!) used.

Of course, as an audience member, I wouldn’t want to see one of us spend the whole “Vacay” on a plane. A big part of the point here is the destination(s). If I do manage to double up on destinations, I’ll likely need to make sure that there is some bit of local flair that demonstrates why I’m there.

Still, it’s hard for me to imagine a big trip that doesn’t include at least two stops. I have mentioned many times before that my wife loves to travel but hates to fly. When we begin thinking about a trip to a far-off place, she almost always wonders what else we could see if we’ll already be in a particular far away destination. I am rarely ever planning a trip to just one place. I might have to adjust my thinking on that here in favor of a 5th night free booking of some sort, but I feel like I might get stir crazy if I spent 5 nights in the same hotel, so the jury is still out on this.

Bottom line

I chose Amex Membership Rewards because I love how easy they are to accumulate, their excellent slate of transfer partners, and because I think they are under-appreciated when it comes to strength for booking hotels. Furthermore, frequent transfer bonuses should make it easy to stretch the value of my points further. While they have some excellent unique transfer partners, I am more tempted to use transfer partners available to at least some of my competitors in order to demonstrate just how useful any of the transferable currencies can be — and, ultimately, why I’ll (hopefully) deserve your vote to win.