My family’s 28,000 mile trip around the world for summer vacation

When my kids went back to school last week, I’m not sure what they said when their teachers asked about what they did for summer vacation. The answer is that we went to 10 countries and traveled more than 28,000 miles in total by plane, train, and cruise ship over the course of about 5.5 weeks, flying all of the long-haul flights in business class and staying at some terrific hotels along the way. A number of followers on Instagram asked how we booked the trip. There isn’t an easy answer to that question since we pieced together a number of things, so I wanted to write a post to explain the fuller picture about how we booked the trip.

Fair warning: this is a very long post. I don’t expect that everyone will be interested in every detail. The next section has the short story — feel free to skip around to whatever interests you otherwise.

The big picture

Above is the map showing all of the flights/cruise stops/destinations we visited on this trip. The big picture is that this wasn’t some sort of huge single booking. Rather, we pieced together a bunch of different elements.

That piecing together of different elements is key. I heard from a number of readers who were curious about how we did this, especially because we need four seats, which can seem challenging from an award booking perspective.

However, that seems like a bigger hurdle than it is. I often find that flights connecting other regions of the world — which is to say flights that are neither to nor from the United States — are much easier from an award availability standpoint.

But “easier” is not the same as “easy”. The most important piece of the story is that we didn’t hesitate; when we saw a great opportunity, we booked it and then we pieced things together around the opportunity. That’s the biggest takeaway for anyone struggling when trying to redeem for a family — flexibility certainly helps make a trip like this possible, but you also need to be willing to jump on the availability you find now and worry about the rest of the details later. We didn’t book all of it in a day or two but rather booked the long-haul stuff as we found it and filled in the gaps as plans firmed up. More on that to come.

To wrap up the trip in very simple terms at a high level, this is what we booked:

• A one-way award to Europe on JetBlue in business class
• Cheap cash tickets within Europe to Scotland, Poland and Italy
• A “free” 7-night MSC cruise of the Adriatic Sea
• A one-way award on Air France in business class via Virgin Atlantic for one leg within Europe
• A complicated one-way Aeroplan award with a stopover and a few long layovers that took us from Europe to Mauritius and Asia in business class
• A one-way business class ticket from Tokyo to New York via Honolulu on Hawaiian Airlines. This was a “cash” ticket where we used points at a value of ~1.5cpp, paying about the same number of points as an award ticket but earning miles on the flights.
• A bunch of great hotels using points, a couple of cheaper cash stays, and one using Hotels.com gift certificates and a Best Price Guarantee claim

I’ll fill in those bullet points with more detail in the sections below.

Getting to Europe on JetBlue in Mint (business) class via Qatar Avios

For the first big leg of the trip, we flew from Boston to Dublin in JetBlue Mint class (business class). We had reported last year about a smoking deal to book that route in business class for just 38,750 Avios per passenger (note: that didn’t last long — the price soon went up to 78,000 Avios one way). I have long advocated for striking while the iron is hot, so I jumped on that deal and booked four seats for my family to fly to Dublin while it was available for 38,750 Avios per passenger.

I should add some context: A couple of days before the JetBlue-via-Qatar deal happened, we had booked a cruise departing Venice. We originally had a “free” MSC cruise from the Ocean Prime match that was scheduled for April 2024 that had gotten canceled by the cruise line around November 1, 2023 (they cancelled that cruise entirely). They offered to let us rebook on a different cruise of our choice. We liked one departing Venice on August 5th. Even though our Ocean Prime status expired on June 30th, they let us rebook for August presumably because they cancelled our original cruise.

Within a day or two of booking the cruise, I had also redeemed Capital One Shopping rewards for StubHub gift cards and purchased tickets for my wife to see Taylor Swift in Warsaw, Poland on August 2nd — three days before the cruise departed Venice. That was thanks to a reader tip that tickets were far more reasonable for some of the foreign shows. Floor seats would have been about $300 per seat before fees at the time I purchased, but I went with lower bowl for about $400 per ticket after fees. That’s still the most I’ve ever spent on concert tickets, but take a look at the going rate to get in the door for the rest of the shows in North America and you’ll understand why I jumped on that (particularly with Capital One Shopping rewards, which can only be redeemed for gift cards).

Again, the Taylor Swift show was in Warsaw on August 2nd and the cruise was from Venice on August 5th. The timing was fortuitous: I booked the cruise and found the Taylor Swift tickets 3 days before the Jetblue-via-Qatar deal broke. So when the JetBlue deal came out, I already had plans to go to Europe, but didn’t yet have any flights booked to get to Europe for the concert and cruise. When I saw the JetBlue deal, the only question was which day to fly to Dublin.

I decided to book tickets from Boston to Dublin departing 1 week prior to the concert (we departed Boston on July 26th).  At the moment when I booked the JetBlue tickets, I didn’t know exactly what we’d do during the week leading up to the concert or how we’d get to Warsaw (or when / how we would get back home), but I knew that business class across the pond for 38,750 miles wasn’t going to last for long (and it didn’t).

If you’re asking “Why Dublin?” since my plans were in Warsaw and Venice, the answer is because the flight across the Atlantic is the one that really matters to me. I want to be in a flat bed seat overnight on the way to Europe. Flights within Europe are often pretty inexpensive (and there are lots of award booking options), so I knew I could find a way from Dublin to Warsaw later. I didn’t worry about the details, I just hopped on the deal for the “big” redemption (business class overnight across the ocean). That’s often a necessity when you’re looking for multiple seats in business class — you’re probably not going to find the “perfect” itinerary with all of the associated puzzle pieces in the same magical moment, so you have to be ready to jump on the deal you find and be willing to work out the rest later. It obviously helps that dates fell perfectly within summer vacation from school and that both my wife and I have flexible, online jobs.

At some point down the line, my sister decided to join us for the first week of the trip (and go to the Taylor Swift concert with my wife), so I ended up needing a fifth seat on that JetBlue flight. When she initially decided to join us, there was no award availability on the Jetblue flight from Boston to Dublin. Instead, I booked her to fly separately on American Airlines using AA miles as a placeholder. I did that because it cost a reasonable number of miles from her home airport (57,500 miles one way in business class on AA) and because American Airlines offers free award cancellation. I knew that if I later found a seat on JetBlue, I could book her on JetBlue with us and cancel the AA flight without any penalty.

Sure enough, that’s what happened: a couple of weeks before departure, I found another seat available on JetBlue in business class via Qatar Airways. The price was now 74,000 miles one way (and she doesn’t live in Boston, so I had to get her to Boston with a separate ticket). That was a significantly worse deal than flying her on AA, but at the same time it seemed to be both more convenient and more fun to fly together, so I booked her on a Spirit flight to Boston and then on JetBlue with us to Dublin and I cancelled her award on American Airlines.

That got us to Dublin, but we didn’t have any intention to visit Ireland on this trip.

Dublin to Scotland: A cheap Ryanair flight

My kids sometimes use an educational app called ABC Mouse. There is a unit in the app about Stirling Castle in Scotland. They loved that unit and for a long time they watched it over and over and frequently asked if we could go to Stirling Castle. I’d never felt a particular draw to visit Scotland (nothing against Scotland, it just bever called my name), but since miles and points could actually make that happen for a reasonable cost, we decided to lean into their interest and plan a visit to Stirling Castle. A quick flight from Dublin to Scotland was a no-brainer.

Aer Lingus has numerous daily flights from Dublin to Glasgow or Edinburgh. We ultimately decided to base ourselves in Edinburgh. I dragged my feet on booking this part of the trip and by the time I got to it, the only Aer Lingus flight with award availability was only bookable through Aer Lingus Avios, not partners, and the departure time wasn’t very desirable. Furthermore, I didn’t think the award ticket would come with free checked bags. Cash prices were cheap, so the Avios wouldn’t save us a substantial amount of money. We ended up going with a really cheap Ryanair flight and used a Ritz-Carlton credit card to pay for it so that we could get all of the baggage and seat selection fees reimbursed afterwards via secure message, which was the majority of the cost. That proved to be simple, so we got back $300 of the $367 that we paid for all 5 of us on this flight.

Edinburgh: Stay at the W Edinburgh

I reviewed my stay at the W Edinburgh here. We used a bunch of 85K Marriott free night certificates on this stay. While this wouldn’t have been a great use of points, I was happy enough to use the free night certificates to save a bundle of cash.

I’ll note that while rare for Europe, we were indeed able to book a room with 2 beds for 4 people (2 adults and 2 children) at the standard room award rate. That was part of the reason we chose this property as it is otherwise very difficult to find award rooms that accommodate 4 people in much of Europe.

What we did in Edinburgh

Our primary reason for traveling to Edinburgh was to go to Stirling Castle. We traveled from Edinburgh to Stirling via train and walked up to the castle and back down to the train station.

One of my reasons for choosing the W was because of its close proximity to the train station. That made it very convenient. Side note: we traveled from the airport in Edinburgh to the center city via the tram from the airport, which was very convenient. My sister accidentally left her backpack on the tram as we scrambled to get everything off. There was a phone number on the kiosk at the tram stop to call for help, so she called. To all of our astonishment, the call center was able to call someone on the tram who was able to grab her bag and bring it to the driver, who brought it back to the same stop on their next lap around. Talk about lucky!

Stirling Castle itself was a decent castle to visit, though with the number of castles one could visit in Scotland and my lack of knowledge/experience about those options, I wouldn’t recommend it over anything else. The kids were thrilled to get ice cream inside of Stirling Castle. And we found great hats for them for the upcoming winter season!

Back in Edinburgh, we walked a bit of the city, visiting a cemetery where I guess JK Rowling got some of the names for Harry Potter characters and we saw the Elephant House, where I guess she lived while writing some of the story (can you tell I’m not a big Harry Potter fan?).

We also went to the National Museum of Scotland, which is an awesome free museum. Both the kids and the adults loved it. I’d unequivocally recommend the National Museum of Scotland it if you visit Edinburgh. Exhibits were educational, interactive, and interesting. Everybody learned something. A quick snippet of the museum here:

 

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We also ate at Dishoom. If you go to London or Edinburgh, do not miss the Chicken Ruby at Dishoom. You don’t have to take my word for it — after you watch this reel, head over to our Frequent Miler Insiders group where a reader recently reported their experience at Dishoom after seeing me post about it on Instagram (and many other readers chimed in with their thoughts in the comments on that).

 

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Warsaw via Poznań, Poland: A Ryanair flight + a LOT Polish flight

The most direct route from Edinburgh to Warsaw was a nonstop Ryanair flight to a secondary Warsaw airport (WMI, whereas most flights to/from Warsaw utilize WAW. There were no nonstops to WAW from Edinburgh or Glasgow). I nearly booked that Ryanair flight to WMI, but I read a number of really negative reviews of the airport. Specifically, I read numerous complaints of the arrivals hall being so overwhelmed with traffic that the wait for immigration can sometimes be a couple of hours. Worse, the arrivals hall itself is apparently pretty small and quite a number of reviews mentioned being forced to wait outside (like on the tarmac) for extended stretches without cover from sun or access to restrooms. Given our group dynamics, that didn’t seem realistic.

I should note that connecting flights from Edinburgh to WAW, the main Warsaw airport, were wildly unreasonable by the time I got around to booking this part of the trip, no doubt thanks to Taylor Swift having 3 consecutive nights of shows.

I ended up opting instead for a cheap enough Ryanair flight from Edinburgh to Poznań, Poland. It would be just a cheap train ticket or domestic flight to Warsaw from there.

The flight from Edinburgh to Poznań was $687 total for 5 of us including our checked / carry-on bags and seat selection for everyone. We got $300 of that reimbursed by using another Ritz-Carlton card to pay the fees (my wife and I both have Ritz cards).

A train ticket to Warsaw would have run $20-$40 per person. Flights on LOT Polish were about $75, so we used Chase Ultimate Rewards points, booking through Chase Travel and using my wife’s Sapphire Reserve account so we could redeem at a value of 1.5c per point — we redeemed 25,100 Ultimate Rewards points for our 5 tickets to from from Poznań to Warsaw. We spent the day in the Poznań airport before flying on to Warsaw. I got work done and my wife did school work with the kids.

Warsaw hotel: Hotel Verte, Marriott Autograph Collection

In Warsaw, we stayed at Hotel Verte, which is a Marriott Autograph Collection property right on the edge of the old town area. It was a very nice property that is often very reasonable from a cash rate perspective. From an award standpoint, this was a slammin’ deal given the effect that the Taylor Swift concerts had on room rates. Whereas I saw rates in the 150-250 Euro range for the Hotel Verte outside of the concert dates, rates were in the ~700 Eur per night range for the concert. We booked two rooms for 3 nights each for 151,000 total points per room. There was no resort fee.

Not only was the hotel very nice (I’d say it was a solid 4.5-star place), but they really leaned into the fact that most people staying at the hotel were there for the Taylor Swift concerts. For our three nights and days in Warsaw, the hotel only played Taylor Swift music all day and night, they had a selfie spot set up with life-size cutouts of Taylor Swift, and they had a friendship bracelet-making station set up the entire time with free supplies to make bracelets. I’m not a Swiftie myself, but I appreciated what that did for the excitement in the hotel. Keep an eye out for a separate bottom line review of the hotel to come, but the true bottom line is that I’d gladly stay there again.

Here was a quick look at the friendship bracelet making station:

 

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What we did in Warsaw

We arrived late on the first night, so we had one full day + the day of the concert (my wife and sister left early for the show) and then we were all moving on, so we really had one “full” day in Warsaw without much along the lines of goals (since the concert was the main goal here).

After a couple of days of museums in Scotland, our kids had to get in some play time. One of the tips I’ve given in terms of family travel is to find a playground every few days. We did exactly that in Warsaw, finding a playground where the kids could run around for a couple of hours. Then we strolled a bit of the old town area and found a highly-rated restaurant known for its pierogi. It was delicious!

The next day, we spent some time at the friendship bracelet-making-station in the hotel. After my wife and sister left for the concert, my sons and I walked through old town Warsaw some more and enjoyed some delicious treats. I’d like to come back to Warsaw again and explore more.

 

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Warsaw to Venice: LOT Polish booked through Chase Travel

I had intended to book award tickets from Warsaw to Venice since there was award availability in economy class for 12,500 Air Canada Aeroplan points on LOT Polish. However, taxes were more than $50 per person.

By comparison, a cash ticket in economy class was $211 per person. That meant that if we used Aeroplan points, the 12.5K points would only be saving us about $160 per person. That didn’t excite me. Instead, I booked via Chase Travel and used a little over 56,000 Ultimate Rewards points for all four of us (about 14K points per person with no additional taxes to pay).

Venice Hotel: Hyatt Centric Murano

“In Venice”, we stayed at the Hyatt Centric Murano. That’s in quotation marks because the Hyatt Centric isn’t really located in Venice but rather on the island of Murano, famed for its glass production. Murano is about a ~20-minute water bus (Vaporetto) ride from the airport and somewhere around the same distance from the first stop in Venice proper. That makes this an unideal location for anyone who wants to be in the heart of Venice or particularly for anyone for whom a 20 or 30 minute walk to get to Saint Mark’s Square is going to be an issue.

That said, there were things to like about this hotel.

First, there is a Vaporetto (water bus) stop literally at the front door. You walk off the dock and you’re at the entrance to the hotel. Make sure to buy a ticket to Murano Museo as that’s the Murano stop that’s right in front of the hotel.

Second,  Murano has a much more relaxed / low-key vibe. After pushing through crowds in Venice all day, it was kind of nice to come back and stroll around near the hotel with a much quieter atmosphere.

Third, we booked an inexpensive rate (~150 Eur per night) for a standard room and used a suite upgrade award to upgrade to a standard suite, which is a room type that accommodates 2 adults and 2 children. It’s worth noting that the savings wasn’t huge over booking a suite with points given that this is a Category 3 property, so you may prefer booking a suite with points from the get-go (which would have been 17,000 points per night total).

The location here will be unideal for most people, but given the price I’d consider staying again, especially since it is possible to reasonably book one room that accommodates four people.

As to what we did in Venice, we arrived at the hotel in late afternoon on August 3rd, so we only went into Venice on August 4th. On the morning of the 5th, we packed up and headed to the cruise terminal. That meant we only really spent 1 day in Venice. Was it worth it? You betcha. Here were some highlights:

 

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“Free” MSC cruise from Venice to Montenegro, Croatia, Greece, and Italy

We next took a 7-night cruise from Venice to Kotor, Montenegro; Durovnik, Croatia; Corfu, Greece; Zakynthos, Greece; and Bari, Italy. This was a free cruise from Atlantic City status matching. I previously wrote about the cruise here. We really enjoyed the stops on this one. We look forward to visiting Kotor, Montenegro and Corfu, Greece again next year and would be happy to explore a bit more around Bari, Italy in the future. Since I reviewed the cruise separately, I won’t go into more detail about it here.

Here were video highlights of just Kotor:

 

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A couple other cruise highlights:

Venice to Paris: Air France Business Class via Virgin Atlantic for 9,000 points + ~$22 each

We had an Air Canada Aeroplan award for the next stretches of the trip that was originating in Paris, so we needed to get from Venice to Paris after the MSC cruise.

We ended up booking an evening flight from Venice to Paris on Air France via Virgin Atlantic. This award was in business class because that’s all that was available via Virgin Atlantic from an award standpoint. Economy class was something like 30,000 miles per passenger through Flying Blue, but business class, which included free checked bags, was 9,000 miles plus about $22 per passenger through Virgin Atlantic. Greg has written extensively about this sweet spot before and it came through for us in this situation. When you’re thinking about booking a flight on Air France or KLM, it’s worth checking Virgin Atlantic. They won’t always have a better price than what Flying Blue offers, but sometimes they will and the difference can be substantial.

Venice’s Marco Polo Airport only has one lounge and we’d have had access to it with Priority Pass if not with our Air France business class tickets, so really the only differences over economy were the checked bags, blocked middle seats, and in-flight meal. None of that mattered a ton, but nonetheless it was a good value at 9K + $20 each.

Hyatt House Paris CDG airport

We stayed overnight at the Hyatt House CDG, which has a paid shuttle or is a taxi ride away from the airport, but at 5,000 points it was a good enough deal. We were arriving in Paris a day or two after the closing ceremonies of the summer Olympics, so the cash rate at the time I booked was a ridiculous ~$500 per night, making the award an incredible value.

The hotel itself has kind of a weird design, but they had washers and dryers for guest use, and by this point in the trip he had to do laundry, so this place was a perfect place to regroup. We arrived late and our flight the next day wasn’t until about 4:30pm, so the ability to do laundry and get a late checkout was exactly what we needed.

A big Air Canada Aeroplan award from Paris

We departed Paris on a big Air Canada Aeroplan award. I’ll first list the airport codes for the full award for folks who want the simple story and then explain in more detail with a second set of bullet points:

• CDG-MRU on Air Mauritius in business class
• 5-day stopover in Mauritius for 5,000 additional Aeroplan points per passenger
• MRU-KUL on Air Mauritius in business class
• KUL-SIN on Singapore Airlines in business class
• SIN-KIX on Singapore Airlines in business class
• KIX-GUM on United in economy class

I manually found each of those segments available via the Air Canada website and then called to book over the phone. Actually, I originally booked a similar-but-different award that went to Mauritius and ended up at Victoria Falls, but we later decided to change the destination to Asia and an Aeroplan agent was able to help us make that change without losing the seats we had on the flight to Mauritius (I wrote about that change here). We paid 115,000 miles plus about $250 in taxes per passenger (that includes the extra 5,000 miles each for a stopover in Mauritius).

Here is the more detailed explanation of the above:

• Paris (CDG) to Mauritius (MRU) on Air Mauritius in business class. Note that this route very frequently has 4 or more seats available in business class — we basically had our pick of almost any day for this segment.
• 5-day stopover in Mauritius (which cost an additional 5K points per person). I planned the stopover for 5 days thinking that we’d stay at a Marriott or Hilton property on the island and take advantage of a 5th night free award booking, but we ended up at the Lux Belle Mare instead, which I reviewed here.
• Mauritius (MRU) to Kuala Lumpur (KUL) on Air Mauritius in business class. Again, Air Mauritius tends to have 4 to 8 seats available in business class on many (most?) of its flights, so this was an easy get. We also considered flying to Perth, Australia on Air Mauritius, which was also an easy get in business class. I’ll note that the Air Mauritius in-flight experience was “fine” — seats were OK, food was OK, service was friendly. I wouldn’t go out of my way to fly Air Mauritius, but neither would I avoid it — and given the good availability they have (no doubt thanks to limited partnerships with other airlines), they can be a good option for connecting dots.
• We had an ~8hr layover in Kuala Lumpur. I had intended to rent a car and take the family to the Batu Caves, which we did during our Flying by the Seat of Our Points challenge earlier this summer, but 75% of the family hadn’t slept enough on the flight to Kuala Lumpur, so we made a game-time decision to instead book two rooms at the airside transit hotel in Kuala Lumpur, so we didn’t leave the airport. This worked out to be a wise decision as everyone got a nap, which I think helped in making the time zone change to Asia.
• Kuala Lumpur to Singapore on Singapore Airlines in A350 business class. This was easy enough to find for four passengers on almost any day given the fact that it’s only a 1hr flight — they simply aren’t going to sell out the business class cabin all that often on such a short flight, so it’s often available for award redemption.
• We next had a ~16.5hr layover in Singapore. I planned this layover specifically to return to J2 Famous Crispy Curry Puff in the Amoy Street Food Centre, which has Bib Gourmand honors (sort of like a Michelin guide “honorable mention”). Long-time readers may remember that I got one of these crispy curry puffs during the 3 Cards 3 Continents challenge a few years ago. I was very excited to wake up first thing in the morning and go get these again! We stayed at the Westin Singapore specifically for its proximity to the Amoy Street Food Centre so I could get a crispy curry puff before breakfast at the hotel. After breakfast, it was more or less time to head back to the airport for the next leg, but a full night’s sleep meant that everyone was reasonably ready to be on Japan time on the next leg…
• We next flew Singapore to Osaka, Japan on Singapore Airlines in 787 business class. This was the challenging part of booking this award. We couldn’t find availability from Singapore to Tokyo any time during the several day window when we wanted to travel and could only find one option to Osaka with 4 seats in business class, so this flight really dictated which day we were flying from Mauritius to Kuala Lumpur and on to Singapore, because we had to arrive within 24hrs of this flight to keep everything on a single award ticket. We could have worked this out to spend a night in Kuala Lumpur instead, but I wanted my crispy curry puff, so we made it work to arrive in Singapore as close to 24hrs before this flight as possible (which ended up being about 16.5hrs ahead).
• Our award was booked with a 23hr and 55min layover in Osaka, which was literally 5 minutes below the maximum allowed layover (24 hours or more would be a stopover and you can only have one stopover on an award, which had already been Mauritius on this award that originated in Paris).
• Osaka to Guam on United Airlines in economy class

We originally intended to continue on with the trip from Guam, but we ended up having trouble finding award availability to connect the dots we wanted from there, so we ended up deciding to stay in Japan.

There were a couple of good takeaways from this experience:

• Surprisingly, we didn’t have any issues with checking in for any of our flights on this Aeroplan award. While I’ve previously done complex Aeroplan awards, I’ve gotten confused looks at the check-in counter more often than not about where I was going since the ultimate destination of the one-way ticket didn’t seem connected to the parts and pieces. This time around, nobody seemed phased at all.
• Another pleasant surprise was that we had no difficulty at all checking our bags from Mauritius to Singapore for our 16.5hr layover in Singapore. I simply explained at the counter that we were staying overnight in Singapore and wanted to get the bags there. I was skeptical as to whether this would work because this meant that Air Mauritius would carry our bags to Kuala Lumpur and then have to hand them off to Singapore Airlines, with whom they have no codeshare partnership as far as I know. However, the Air Mauritius agent understood what we wanted and I watched the bag tags get applied to the bags with both the KUL and SIN airport codes, so they obviously knew what they were doing. I had thought that might at least require getting some help from another agent, but it was really easy.
• Similarly, we received no pushback in checking our bags from Singapore to pick up in Osaka thanks to the 23hr and 55min layover on the ticket.

Again, this ticket cost us 115,000 points per passenger (x 4) and about $250 each in taxes & fees (a total of 460,000 Aeroplan points). I’ll point out that about some of the points for this award had come from my wife building her own Bilt bonus to take advantage of the Aeroplan transfer bonus a while back. I had forgotten that we had joined family sharing back when Aeroplan had that feature available (it’s “on hold” right now, but expected to return at some point — in the meantime, people who joined while it was available are unaffected). That was convenient because we could pull the Aeroplan points for the award from our combined balance.

This was without a doubt a big award that both involved a lot of travel, a fairly unique partner (in Air Mauritius), and a substantial number of miles. I don’t regret it at all.

I should emphasize that finding 4 seats on all but one segment here was incredibly easy. That actually made booking very simple because I just needed to reverse engineer to connect the dots based on the day that the flight from Singapore to Osaka was available. I mention that because one comment/question I received frequently during the trip was about the difficulty of finding business class seats for 4 passengers. That actually wasn’t very difficult at all. I often find that flights connecting regions outside the United States tend to be pretty easy and this trip tracked with that.

To be clear, I used tools we’ve written about before for planning our route. For example, I knew I wanted to go to Mauritius and that my best shot at finding award availability from Mauritius to somewhere else would be on Air Mauritius, so I used FlightConnections.com to see which airports Air Mauritius serves.

Originally, we had decided on the flight to Johannesburg and then onward on South African Airways to Victoria Falls, but we later decided to go to Asia on this trip instead. Realistically, that left us connecting via Kuala Lumpur or through India. I knew that Singapore was only an hour flight from Kuala Lumpur and that Singapore Airlines has good coverage throughout Asia and I wanted my crispy curry puff, so I quickly decided to see if I could get us to Japan and onward from Kuala Lumpur.

The biggest hurdle in booking this award is that Air Canada requires that your total distance from origin (Paris in this case) to final destination is not longer than double the nonstop distance from origin to destination. I needed to end up farther from Paris than Japan. I knew that United had a flight from Tokyo to Guam but had forgotten about the Osaka-to-Guam route. That fit perfectly to stretch the award as far as we needed it. I had stumbled on that flight more or less by accident when I searched for flights from Singapore to Guam (I had expected to see something connecting in Tokyo — the connection in Osaka was a pleasant surprise).

Mauritius: Lux Belle Mare

In Mauritius, we mostly hung around our resort, Lux Belle Mare, which I booked through Hotels.com using rewards earned from Capital One Shopping. You can read my full review here. In short, this was a beautiful little spot to spend a few relaxing days.

We also visited the National Museum of Sugar (where we bought some local vanilla and a wide variety of types of sugar) and the botanical gardens, but given the narrow and windy roads on the island, we couldn’t explore as much as most would probably like since our younger son has difficulty with motion sickness.

Kuala Lumpur Airport (KUL): Sama-Sama Transit Hotel

The airside transit hotel in Kuala Lumpur Airport came in handy for us since we all needed a nap after the flight from Mauritius to KUL. That was an overnight flight, but at around 7hrs, it just didn’t provide enough time for a full night’s sleep.

We needed to get 2 rooms at the transit hotel because, although the hotel does have some rooms that accommodate a family of four, none were available. The rooms were clean enough (there was a hairpin on the dresser in my room, but beds, sheets, and bathroom were all clean).

That said, it feels almost criminal to pay the rates they charge knowing that for what we spent for two rooms in the airport we could have had a full five-star luxury hotel for the night in Kuala Lumpur (and probably with Amex Fine Hotels & Resorts benefits). Each room was about $112, so we paid more than $220 in total. However, given the hours we were there, this was our best option.

I’ll add that while reservations at the hotel are for 6 hours, you have an option to add additional hours during the booking process for 50 Malaysian Ringgits per hour (about $11.50 based on the current exchange rate).

Singapore: Westin Singapore

The Westin Singapore is on par with what you’d expect for an upper midscale foreign chain in Asia, which is to say that it is far nicer than what you’d expect from a Westin in the US, though not at the top end of luxury. Most foreign chains tend to be very good in Asia and this property was no exception. The room was nice, beds were comfortable, and restaurant breakfast was fairly extensive (and complimentary as a Marriott Platinum member; kids ate for free in the restaurant as part of an ongoing promotion for Marriott properties in the Asia-pacific region). We took a taxi both ways from the airport to the hotel and back.

When we arrived at the airport, I tried to use Grab (an Asian equivalent of Uber), but the driver was taking forever to arrive. We ended up going with a taxi. I thought for sure we would need two taxis because we had quite a bit of luggage, but to my surprise the driver encouraged us to give it a shot and we packed it in. We ended up being able to do the same on the way back to the airport.

Osaka: Caption by Hyatt Namba Osaka

When we arrived in Osaka, we spent three nights at the Caption by Hyatt Namba Osaka. This was a brand new property (opened in June 2024). As a Category 1 off-peak, it cost just 3,500 points per night, which was an incredible deal and made for an easy decision on accommodation — I just couldn’t seriously consider staying anywhere else. Unfortunately, the rooms accommodate a maximum of 3 people, so I had to book 2 rooms. As it turned out though, that wasn’t so bad. We arrived in Osaka quite late (we got to the hotel around midnight) and I had a Frequent Miler team meeting at 1am local time followed by another Zoom call at 3:30am local time, so it was just as well that I had a separate room from which to do those Zooms. The next day, we recorded our Frequent Miler on the Air episode, and once again it was convenient to have a second room for that.

This deal was also juiced up by the fact that this is a new property, so you earn 500 bonus points per night through September 30th (making for a net cost of just 3,000 points per bedroom per night). I also chose the “2K next stay” milestone reward at 30 nights because that provides 2,000 points on your next stay at Hyatt Place / Hyatt House / Caption by Hyatt, so I earned an additional 2,000 points as well.

I published a quick video review of this property on Instagram that really sums things up well:

 

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The Caption hotel was well-located in Osaka, less than 100m from the Kuromon Market, which is a great little street market where you can get fresh seafood, Kobe beef, and various types of merchandise. We also enjoyed strolling to a couple of arcades with the kids and through various other covered street market areas with knife shops and various vendors.

My wife and I had been to Osaka before and we were really pleasantly surprised with it last time. This time around, we were again struck by how much we enjoyed Osaka and by the fact that we didn’t plan enough time there.

As for the hotel, the one key drawback is that breakfast is very limited. There is a cafe that is reminiscent of a Courtyard by Marriott in the lobby. Globalists can choose from just 3 menu options: a breakfast sandwich set, a pastry set, or a soup/noodle set. There was almost no customization — I wanted the breakfast sandwich with no egg, but while that was made in a kitchen, that couldn’t be accommodated (if you ordered pastries, you could have either a croissant or an apple Danish and your choice of one of a couple of small muffins). We asked for both coffee and juice and were told it would be an upcharge to get both (which is actually against Hyatt terms as I understand them, but I wasn’t going to argue that over the two or three bucks…though ultimately we weren’t charged extra). My kids often go through two glasses of milk though and we did have to pay for the second glass. Let me be clear: I’m not complaining. At 3,500 points per night, I’m happy to have a very clean room/bathroom and get Hyatt elite night credit. Getting anything for breakfast feels like a bonus in that case and paying the two or three bucks for an extra milk or two was not at all a concern. However, it does stand in contrast to what Globalists can usually expect at Hyatt properties in Asia, so I mention it to set expectations since this stands out as different. I should also add that I meant to make one room a Guest of Honor stay in my wife’s name but I forgot to make that change. Nonetheless, the hotel honored my Globalist benefits, including both complimentary breakfast and 4pm late checkout, for both rooms.

The hotel technically has a laundry room, but it consists of just two machines that are each a washer/dryer all-in-one. The full cycle takes 120 minutes, which means that at most, each machine can accommodate 12 loads of laundry per day. Finding a machine available was next to impossible. Then, the next limitation was that the machines do not accept cash, nor do they accept credit cards or Apple Pay/Google Pay. They do accept some mobile payment methods, but none that you’re likely to be able to access if you’re from the US. There was a sign saying that you could go to the front desk for help if you’re unable to pay via the QR code, though with almost all of the signage in the room primarily in Japanese, I didn’t even see that sign until the day we left. I got help from another guest who was able to pay and take cash from me one time, but I washed the rest of our clothes at a coin laundry down the street (which was also a little challenging, but doable).

In Osaka, we visited Osaka Castle, went to the Osaka Aquarium (which is amazing – perhaps the best in the world), hit up some arcades to play video games, and strolled the local market.

Osaka to Tokyo via bullet train

To get from Osaka to Tokyo, we took the Shinkansen (“bullet train”). We did this mostly for the experience. Even though our 3yr old did not need a ticket, it still cost us $240 for 2 adult tickets and 1 kid ticket. We could have alternatively booked award tickets to fly Japan Airlines (via British Airways Avios or American Airlines miles) or on ANA via United for around 5K per passenger. The train didn’t feel like much of a deal, but my kids were interested in the fast train, so we considered this part of the experience.

Tokyo: Grand Hyatt Tokyo

We spent 5 nights at the Grand Hyatt Tokyo. I published a bottom line review of our stay here.

Overall, it was a good stay. I didn’t love the location, but look the comments on my post for readers who disagree with me about that. I loved the spacious suite we had thanks to using a suite upgrade award (and then getting upgraded further).

Things we did in Tokyo

• teamLab Planets. The Frequent Miler team went here during our 2023 challenge.
• teamLab Borderless (Amazing. If you go to Tokyo, you have to go. If you can swing it, I think both are worth a visit, but I’d recommend Borderless first and then Planets. Borderless is much larger and will take longer (the Internet says to expect to spend 3-4 hours and I think that’s probably spot on), but the reason I suggest this is because Borderless is set up for you to wander and “discover” the rooms at your own pace. You can (and should) go back to rooms again (they’ll be totally different). On the flip side, Planets is a linear experience that requires going in a single direction where you see each room one after another. In hindsight, there were rooms I wished I’d have spent more time in the first time if I could go back and do it again (and the same thing happened with my kids — they moved through too fast and wished they could have gone backwards again). I think you’ll have a better idea of how to pace yourself through Planets after wandering at Borderless.
• Legoland Discovery Center. This was nothing special. Our kids are really into Lego and this worked for something fun that was indoors (the weather was hot in Japan in August). We knew they would be into it, but this was just an average Lego Discovery Center. The rides are the same you’ll probably find at any other Lego Discovery Center. They did have a cool Tokyo Lego display, with landmarks like Shibuya Crossing and the Tokyo Dome, etc.
• Visited some arcades.
• Went to the Nintendo Store. This has some cool Nintendo merch (I got a luggage tag I like!), and they have a cool huge screen where 8 people can play a test game at once, but it’s really crowded. There was also a Pokemon and Capcom store on the same floor, so it can be cool if you’re really into games. Speaking of games, they are cheaper in Japan (even more so because of the current favorable exchange rate for us), and I guess all of the latest systems and games are region-free. That said, if you want to buy a new Switch or a bunch of games, go to a big electronics store where you can take advantage of tax-free shopping rather than the Nintendo Store (which does not participate in that. Ask me how I know).
• Visited the Museum of Emerging Science and Innovation. This is an awesome museum with lots of wild robotics on display and plenty of other interesting exhibits. My wife and I have been here before and were excited to return. We spent most of a day here.
• Went shopping. We generally don’t buy much of anything when we travel apart from a toy in a museum gift shop now and then. Our bags are usually pretty full when we leave home, so we don’t generally have enough space to buy much of anything even if we wanted to. However, because of the strength of the dollar and the prevalence (and relative ease) of tax-free shopping in Japan, we ended up buying quite a bit of stuff — including two new Muji carry-on bags in which to put stuff (which I long ago said that I like more than my Rimowa carry-on, and that was before the strap to tighten down a divider inside my Rimowa broke on this trip. Grrrr). My wife loaded up on Japanese skin-care products, which were around half the price of similar products in the US, and we even bought some clothes. And we bought Kit Kats (Japan is well-known for its creative flavors). After reading a reddit thread about things to buy in Japan and reading many people rave about the nailclippers they bought in Japan, I bought a set — and I have to say that they are going to be a permanent fixture in my toiletry bag. I actually accidentally bought two sets and it was a great mistake to make.
• Went to Tokyo DisneySea. We stayed at the Hilton Tokyo Bay for this (see the next section). Tokyo DisneySea was a lot of fun. Prices were reasonable (our 3yr old was free and it cost about $160 for 2 adult tickets and 1 child ticket for a full day in the park; meals within the park were reasonable, as were snacks — we got big ice cream sandwiches for about $2.50 each). The attention to detail here is excellent and there were characters to meet all over the place. We got lucky that heavy rains were forecast, so not many people came to the park. It didn’t end up raining much at all, so we didn’t have to fight with long lines anywhere.

Here’s a reel of teamlab borderless:

 

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My kids took on some of the Nintendo games of my youth in Tokyo:

 

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Hilton Tokyo Bay

We spent 3 nights at the Hilton Tokyo Bay, going to DisneySea in the middle. I published a bottom line review of the Hilton Tokyo bay here.

I wasn’t blown away by this place, but it’s hard to beat the convenience. I’d probably either stay here or the Sheraton if I went to visit the Disney parks again, but the excitement here is really just for Disney.

Tokyo to New York on Hawaiian Airlines via Amex Travel

For the ride home, we used points to book a fantastic paid fare.

Since I have a few cards that offer the opportunity to use points at a value of 1.5c per point toward paid airfares, I make it a habit to check paid fares. I was very surprised when I found paid business class from Tokyo to New York on Hawaiian Airlines for about $1,480 per passenger. That price was available into early September travel dates at the time when I found it.

I ended up using the Business Platinum pay-with-points rebate, which gives you 35% of your points back when you book any airline in business or first class (up to 1,000,000 points back per year). That meant that we initially paid 148,000 points per passenger and later got back 51,800 points per passenger for a net cost of 96,200 points per passenger. Since we were using Membership Rewards points to book a paid fare, we earned miles on the trip. I had originally intended to credit to Virgin Atlantic Flying Club, but since the merger with Alaska means that we eventually expect Hawaiian miles to become Alaska miles, we credited to Hawaiian and earned 13,200 miles each. If you value points and miles equally, we could look at it as a “net” cost of about 83,000 points per passenger. That’s on par with what a business class award ticket would cost through many programs and we didn’t have to worry about finding award availability for four passengers. I had assumed that we’d have to take what we could get and fly from Tokyo to any city we could find in the US and then position home — being able to fly to JFK made that a solid deal for us.

Hawaiian Airlines business class was fine. We weren’t on their new 787 with the new suites but rather the old A330. Many people don’t like the open design and lack of privacy, though my wife noted that she enjoyed not having her feet stuck in a narrow footwell. That said, we both noted how awful the in-flight entertainment setup is: they give each person an iPad and headset to use, but because they don’t want people stealing them, they don’t hand them out until you’re in the air and they take them away well before landing. We sat on the ground with a maintenance delay for more than 2 hours before departing Tokyo and there was no in-flight entertainment for my kids to watch. Then my 3yr old was 12 minutes from finishing his movie when they took the iPads away with more than 30 minutes left in the flight. That’s unideal.

Food was not very good and I’d be embarrassed about the lounge in Honolulu if I were in the airline’s management. For an airline that carries passengers between Japan/Korea/other destinations in Asia to have no showers and only kalua pork and some sliced carrot type vegetables to eat is just utterly uncompetitive.

All that said, service on-board was wonderful. The lead crew member on our flight from Honolulu to New York was especially warm and hospitable — she was one of the best in-flight crew members we’ve had on any airline, which is no small compliment. Not only was she great at taking care of us in-flight, but she kept it up after the flight: I left a handbag with all of our passports in it in the overhead compartment on the plane. I realized when I got to baggage claim and I found an airline rep who said that he would radio to have the cleaning team look for it. A little while later, as the crew walked past baggage claim to leave, I saw that same lead crewmember stop the baggage rep to tell him that she’d found a bag left in the overhead compartment (mine!) and passed it to the cleaning team. She didn’t see me, she just took the initiative to let him know. That was really nice.

Overall, I’d fly Hawaiian again if it made sense. It was nice to get a layover in Honolulu — we had about 8 hours, so we rented a car and drove to the Dole Pineapple Plantation to do the World’s Largest Maze and get a Dole whip before heading back to New York. We drove a one-way rental car from New York JFK to Albany to finish up our trip and get back home (found a deal on that via Autoslash.com).

Bottom line

This was a great trip that lasted about 5.5 weeks. All-in, we spent about 269,000 miles/points per passenger for the flights, about 430,000 Marriott points (between two rooms at the Hotel Verte in Warsaw, one night in Singapore, and I think one night paid with points at the W Eindburgh), a total of 130,000 Hyatt points (125K for the Grand Hyatt Tokyo and 5K for the Hyatt House CDG), a net cost of around $700 for the paid stays in Venice and at the Hilton Tokyo Bay, about $1400 in Hotels.com gift cards and another ~$200 in cash on top of the gift cards for Lux Belle Mare, and of course expenses for food, train tickets, etc. There’s no doubt that we wouldn’t be able to do anything like this without miles and points. Not paying cash out of pocket for flights (and not much out of pocket for hotels) makes it possible to splurge on doing all of the things we did on this trip.

For those wondering about how the kids liked it and held up with the pace: in the car on the way home from New York JFK airport, I asked if they’d like to do a trip like this again next year if it were possible (to be clear, I don’t know that it will be). They both enthusiastically said yes. When asked why, they both noted that they liked seeing new places and my older son mentioned that he enjoyed trying new things (specifically noting the Chicken Ruby he had at Dishoom — remembering it more than a month later). That night, when we got home and a family member asked which countries they had visited, I was really surprised at the fact that between the two of them, they were able to name the majority of places we’d been. I’ve said in the past that I understand that they won’t remember all of the details of these trips any more than they’ll remember the details of the bedtime stores we read today, but I love that the games we play with miles and points makes it possible for us to put together incredible adventures like this that I’d have otherwise never dreamed possible.

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