It has been almost two weeks since my last blog update about our experiences and learnings as we make our way to 25 destinations this year for 1.4 million total points and 25 years of elite status. You can see the previous update here. This week’s update includes how we bought Hyatt points for 0.8c per point, a tip to save you from an upgrade you don’t want, a Capital One Shopping experiment with 30% back at Hilton, the makings of a Hertz horror story and more.
Sunday, August 10th: Boston to Martha’s Vineyard (MVY). Airport #13.
The flight attendants said that our flight to Martha’s Vineyard would last for about 13 minutes. As it turned out, it went almost 25 minutes from wheels up to wheels down, but it was nonetheless an easy, uneventful flight to the very small Martha’s Vineyard airport. Baggage claim consisted of a garage door that opened for workers to slide bags over into a baggage claim trough. There’s no moving belt in Martha’s Vineyard, it’s just that small.
We arrived around 9am and called an Uber to our hotel. In hindsight, we should have taken the free bus, we just didn’t know how easy it would be to navigate with kids and bags. If I had it to do again, I’d have taken the bus.
August 10-11: Edgar Hotel Martha’s Vineyard, Acend Collection (Choice Privileges): 45K points per night
We spent the night of August 10th at Edgar Hotel Martha’s Vineyard. I previously reviewed this stay in full here. We really enjoyed Martha’s Vineyard. I’d never felt a particular draw to visit, but after spending some time lounging on a mostly empty beach and strolling the picturesque Edgartown, I can see the appeal. I’d visit again and stay here.
August 11: Island Queen ferry to Falmouth + Enterprise rental car to Boston
Upon checkout on Monday, we took the free Martha’s Vineyard #13 bus from the stop directly in front of the Stop and Shop grocery store (which is directly adjacent to Edgar Hotel) to Oak Bluffs, which is where you can pick up ferries to mainland Massachusetts. Steamship Authority has the main pier by the bus drop-off point. They operate ferries to Woods Hole.
However, since our rental car pick up was in Falmouth, Massachusetts, we opted for the smaller Island Queen ferry service, which is only about a 5-minute walk up the road from the Steamship Authority pier. We booked the Island Queen ferry via the Island Queen app for $54.00 for our family of four (our still-four-year-old was free this time, so we only paid for 2 adult tickets and 1 child ticket). That was more expensive than the Steamship Authority ferry to Woods Hole, but it dropped us where we wanted to be in Falmouth.
That was because we had a rental car reservation in Falmouth. The Island Queen drop off point in Falmouth was about an 11-minute walk from the Enterprise rental car office, so it was easy enough to walk and pick up a car to drive to Boston.
I booked the Enterprise rental car through Priceline after clicking through from an offer for 15% back on rental cars from Capital One Shopping. I got $13.90 back (based on the pre-tax price of $91.32) on a rental that was $102.69 all-in. That’s not a great deal, but between the rental car and ferry, we paid less than $40 per person to get back from Martha’s Vineyard to Boston.
On the way back to Boston, I couldn’t resist the opportunity to stop in Sandwich, Massachusetts and grab lunch at Cafe Chew, Sandwich’s Sandwichery.
I went with The Bavarian: ham with melted brie over apple slices with cranberry chutney on a pretzel roll. I was not disappointed.
August 11-12: Hyatt Regency Boston Harbor (Hyatt Category 1-4 free night certificate)
We once again stayed at the Hyatt Regency Boston Harbor using a Hyatt free night certificate. We’ve stayed here 4 times this month. It’s a good place to stay and it is very close to the airport. They have a free shuttle to the airport, but it is also walkable to at least the rental car center (on a recent podcast episode, I noted that it wasn’t clear whether one section was walkable, but I’ve since discovered that there was indeed a sidewalk that I’d just missed).
A couple of quick tips regarding this hotel:
- If you have Globalist status, the standard upgrade seems to be to a harbor view room (we did receive a suite on one stay, but the rest were to harbor view). If you don’t have Globalist status, the base room is booked into an airport view. I overheard the front desk staff trying to sell many guests on an “upgrade” to a harbor view for an additional $30 per night. If you’re staying in the summertime, save your money. The sunshine coming into the room on the harbor view side makes the room pretty warm during the day/early evening. We have had both and I would rather have the airport view. You can enjoy the harbor view from the restaurant or small tables on the 2nd floor (ballroom floor) or you can dine outside. In the summertime, I’d rather have the room a bit cooler unless you’re really into seeing the skyline at night.
- If you are a Globalist on an award stay and you are parking a car, make sure you stop at the desk to get the parking fee removed from your bill. While they mentioned parking being free for a Globalist on an award stay each time, it had to be manually removed at checkout (the one time I didn’t stop at the desk, it looks like they charged me for it and now I need to follow up to get it reversed).
- If you’re looking for a spot to work outside of your room (in my case, the family goes to sleep at night and I’m often up late getting stuff done), there isn’t much public sitting space (there are 4 total chairs in the lobby and a couple of benches in the first-floor hallways). If you head up to the 2nd floor and walk to the center of it, there are some tables for two that were empty every evening. There’s even a power outlet on the column next to one table.
August 12: Boston to Nantucket to New York-LaGuardia (LGA). Airports #14 and #15.
Tuesday was our tight turn day as we had booked separate tickets from Boston to Nantucket (booked with “cash” through a credit card portal) and Nantucket to New York LGA (booked through Etihad Guest for 6,000 miles and $22 per passenger).
That might not sound like a big deal, but the flight from Boston to Nantucket was scheduled to arrive at 10:30 am and the flight to New York was scheduled to take off at 11:15 am. Unfortunately, we would need to clear security again in Nantucket since planes let off directly into the arrivals / baggage claim area.
Originally, we were unable to check in online for the Nantucket-to-New York flight, but we got that resolved before leaving Boston. I wrote more about that (and how we proactively got a second Etihad-booked JetBlue flight resolved) in this post: Adventures with Etihad Guest: “Fixing” and cancelling JetBlue awards.
We arrived in Nantucket early (around 10:05am), giving us an hour and ten minutes before the flight to New York would take off. That was plenty of time to go through airport security. In fact, while there was a (short) line for passengers with TSA Precheck, there was no line at all for customers without PreCheck, so we sailed right through the checkpoint.
As fate would have it, we sailed through a little too fast. Moments after boarding the plane, one of my kids asked for our Nintendo Switch as the flight continued to board. I went to get it from my bag and realized that I had never picked up the bin with my laptop, our Switch, and my Google Pixel Buds from the security checkpoint. There was a lot going on at that moment (we had to do some additional testing) and my wife took our bags off the belt. I didn’t look back to see that the laptop and Switch were still in a bin. Whoops!
That was a big problem because I had work to do that couldn’t get done without a laptop. I worried that I was going to be forced to buy a replacement laptop in New York. I immediately explained the situation to a flight attendant. She called the front of the plane and said that they’d see if they could get it.
I owe a massive debt of gratitude to the JetBlue pilot who was able to retrieve several items left behind by other passengers at the security checkpoint in addition to my laptop and Nintendo. My day went from ruined to saved in sixty seconds thanks to the pilot going above and beyond. He playfully teased that it was like him showing up for work and forgetting the airplane. I owe him one!
August 12-13: Hyatt Place New York Chelsea
Since we had more than 24 hours between arrival in New York at 12:30pm and our next flight the following day at about 3pm, we decided to head into the city rather than staying near the airport (though we were tempted to go back to the Marriott JFK airport!). I took a bit of a gamble and booked the Hyatt Place New York Chelsea because the rate was good and I’m close to hitting 8 qualifying nights for the current Hyatt Place promotion (I need 2 more to finish out getting the full 16K bonus points).
I say that this was a gamble because the Hyatt Place Chelsea only had a 3.5 rating on Hyatt’s own site. I rarely consider a property with a rating of fewer than 4 stars out of 5. However, I read through the reviews. Almost all of the negative reviews focused on what was described as a glacially slow elevator and a crowded breakfast area. I figured that we would only be there for one night and we probably wouldn’t be up and down so many times as to be very annoyed by the elevators.
Funny enough, at check-in, the desk agent almost immediately said, “I don’t know if you are aware of our reviews, but I want to be very transparent: the elevators can be really slow. Right now, I’ve got you a room on the 7th floor. That shouldn’t be too bad. If you’d prefer a high floor, we can look for something, but to be totally honest, you’re probably better off on 7.” I really appreciated this! I could see a lot of places just “upgrading” Globalists to a “high floor” with a “view”, but not having to wait for the elevator to climb to the 40-45th floor (yes, there are 45 floors in this hotel!) probably alleviated the slow elevator issue for us. We never waited very long for an elevator despite the multitude of complaints. The desk agent also warned us (and I overheard many others being warned) that breakfast gets really busy between 8am-10am, so the earlier you can get there, the better. We arrived at breakfast around 7:45 am and found the last four seats that were somewhat together (two high-top tables for 2). By 8:15 am, it was a bit of a madhouse. The narrow hallway to the buffet room just made it feel all the more cramped. We were fine, but I’m glad we didn’t get there at 8:30 or 9am. I should note that we took the stairs on the way down to the buffet rather than waiting for the elevator, but we took the elevator back up and the wait wasn’t all that bad.
As noted in a caption above, I was about to book the Hyatt Leverage rate at this hotel for $175 + tax (about $203 all-in), but then I noticed that the Member Rate was $194 + tax and there was a special rate for $195 + tax that included 3,000 bonus points. That rate with bonus points came to $227 all-in. That seemed like a great deal to me! We’d pay $24 more than the Leverage rate for 3,000 additional points – a cost of 0.8c per point! Our Reasonable Redemption Value for Hyatt points is 1.8c per point, so I was happy to buy at 0.8c. That was a great reminder to me to look at all of the rates, not just the cheapest one.
After getting checked in, we went for pizza, stopped at the nearby Lego store for the kids, and hit up the playground in Madison Square Park, which was surprisingly nice. There was a splash pad that our kids desperately wanted to use, but with no way to dry our clothes before the flight the next day, they had to stick to the playground. They had made a group of friends by the time we were left.
Overall, I was happy enough with the Hyatt Place Chelsea.
August 13: New York JFK to Hyannis (HYA – Cape Cod Airport). Airport #16.
On Wednesday, we flew from New York JFK airport to Hyannis on Cape Cod. This was another very short and largely uneventful flight.
However, when we arrived at the Hertz rental counter to pick up our rental car, things got weird.
The makings of a Hertz horror story
There was a lone employee at Hertz when we arrived at Cape Cod airport. She seemed overwhelmed, and we soon found out why: Her computer system was down entirely. She was hand-writing rental agreements, working off a printout of the day’s reservations. A woman in front of me who had reserved about an hour before arrival was told that they were sold out and couldn’t honor the reservation, though I suspect the real problem was that they didn’t have computer access to see recent reservations.
Moments before it was our turn at the counter, a woman returned the keys to a sedan. She reported the mileage and that it was full of gas and clean. Since the Hertz employee was on her own, she offered the car to us, sight unseen, telling us to come back in if there was any problem with the car.
The car was fine, but imagine the situation: The customer before us had dropped off a car, but with no functioning local computer system, it had not been registered in the Hertz system as having been returned. Now I was taking this car which, as far as the Hertz computer records show, had not been returned nor assigned to me. This felt like a horror story waiting to unfold.
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Still, we needed to get to Boston and didn’t immediately know how else we’d get there. We took the car, holding our breath and hoping for the best.
The next day, we were at a shopping mall when I got an emailed return receipt from Hertz, saying that the car had been returned at Boston Logan Airport (with a final odometer reading of about 100 miles more than it had when we took it). The problem was that, as far as I knew, the car was in the parking lot at the mall…..and we had already driven more than 100 miles.
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That really made me worry about how this was going to turn out. Given that Hertz had to pay out a huge settlement a couple of years ago for people who were wrongfully arrested for “stealing” cars that they had returned, I told Greg that he should get bail money ready. I didn’t imagine that things would go smoothly when I arrived at the airport a day later to return a car that their records showed was already returned and with more miles on the odometer than the return receipt shows.
Luckily, it turned out to be no issue at all. We returned the car, and everything was somehow fine. That doesn’t really make sense to me and the return receipt in my Hertz account still shows that it was returned a day earlier than I really returned it, but I guess all is well that ends well.
The reason we were at a shopping mall outside of Boston is that we surprised the kids by taking them to a Camp x Bluey experience. My younger son loves Bluey and was thrilled to run around the replica of Bluey’s house and participate in the program. We published a quick reel about it, including how you can save money on tickets.
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August 15: Boston to Milwaukee (Airport #17).
On Friday, August 15th, we made it to our 17th airport of the challenge, Milwaukee. I believe this was only the second flight that had Even More Space seats near the front that we weren’t able to snag at check-in. The flight was full and those seats were gone before check-in began!
However, we were happy with the seats we had chosen at booking.
It is probably worth a mention that after completing 17 airports, the only significant delay we’ve experienced was our flight from San Juan to White Plains during the first weekend run. That flight was delayed because my son’s seatbelt was broken. We’ve had a great run otherwise!
August 15-17: Hilton Garden Inn Milwaukee Northwest Conference Center with 30% back via Capital One Shopping
We spent two nights at a Hilton Garden Inn. We’ve actually stayed at this property once before and wouldn’t again. It isn’t terrible, but there isn’t anything great about the place, either. It is clean enough for two nights at the right price, but not as clean as I’d like. Service at the front desk has been friendly on both stays, I just feel like the rooms could use a deep clean and a refresh. At the price point, there are surely many other places to stay. We chose the property in large part because of its relative proximity to where we needed to be, but we’ll try something else next time.
The other key reason we chose this place is because I had a Capital One Shopping offer for up to 30% back at Hilton (the headline rate is only for select brands, but Hilton Garden Inn is one of the qualifying brands for that rate).
I’ve occasionally run into issues with Capital One Shopping rewards on travel purchases. Terms at Capital One Shopping indicate that travel-related bookings may show up as “ineligible” until after travel is complete, but I’ve had a few that didn’t seem to update to showing rewards even after travel was complete.
We needed 3 total rooms (we met other family members in Milwaukee). I booked the first room at the Hilton Honors flexible rate. Initially, the stay showed as “ineligible” in my Capital One Shopping account. While I had partly expected that, I also thought there was a chance that booking the “Hilton Honors Member” rate had made the first room ineligible. I later booked the two other rooms at the general “Flexible” rate (not the Hilton Honors Flexible Rate). Room rates had dropped by a few bucks overall, but I didn’t bother to rebook the first reservation. All three reservations ended up showing up as “ineligible” ahead of the stay. I thought I might need to follow up with Capital One Shopping after the stay.
However, a few days after the stay was completed, all 3 reservations updated from “ineligible” to “pending”. Note that the “purchase amount” field below shows higher numbers here, but the shopping rewards amount almost corresponds with 30% back on the room rate before taxes shown above (it actually seems more like 36%).
My account shows that one of those will become payable in about a week and a half. The other two become available in mid-September. I expect them to stick.
A couple of important notes come out of here: first of all, it is true that travel bookings may show “ineiligible” before (and after) travel has been completed and those may update later. Second, I was able to click through a targeted email offer multiple times and get the expected return more than once. Third, because we were booking directly with Hilton after clicking through, we also earned around 6,000 points per room. While I wouldn’t be in a hurry to stay again, this worked out well.
We were in Milwaukee for a couple of days to see family. Then, we flew American Airlines eastward to visit family in a different city and slow down for a few days. After the first two weeks of the month, we needed the rest.
The final flights of the month coming soon (Airports #18, #19, and #20)
Today, we are flying back to Boston (airport #18) and then we’ll soon be on to Traverse City, Michigan (#19). After a few days in Traverse City, we’ll take an American Airlines positioning flight to better position ourselves for a return to our home airport, Albany (ALB), which will be airport #20. That should earn us 1.4 million JetBlue points (350K per passenger x 4).
Promo points may post much later than we’d planned
I expected that those points for reaching 20 airports would be awarded within a couple of weeks of reaching airport #20, but some readers have reported that customer service has indicated that we may not see the points until we either complete 25 airports or after the promotion ends. That will be a big bummer. We intended to use already-planned trips to reach the final 5 airports, but those won’t be until later in the year. I had hoped to use some of the points earned from reaching 20 airports to book the final 5 flights. Further, we had intended to hit airport #25 with a flight to visit relatives for Christmas, which is cutting it too close to the end of the year if something goes wrong (either a failure of an already-flown flight to credit correctly or our plans getting thrown up in the air later on). We may need to re-think our plans for picking up at #25 to give ourselves some buffer zone time to see whether we need to re-do anything.
Bottom line
We’ve had a great time flying around on JetBlue this month. The first two weeks were a bit of a frenzy, mostly focused on picking up as many airports as possible. However, along the way, we were able to test out Mosaic benefits, stay at some interesting hotels, and sneak in a little fun for the family. This promotion has certainly brought back memories of our days flying JetBlue’s All You Can Jet promo back in 2011 and reminded us that we like JetBlue quite a bit. I wish they had a more robust route network out of our home airport (or easier connections), but I can certainly see the appeal for those based in New York and Boston. I hope they come out of this thing well because I’d be happy to be more loyal to JetBlue in the future if they could get me where I’m going more often.
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Aww you were in Burlington, I wish I’d known to give you some great restaurant and shopping tips! Hope my home city of Boston treated you well.
Good luck with Hertz. They are an evil company. They came after us months after we returned a car, just out of the blue. They claimed we had done thousands of dollars of damage to the car, and their “proof” was a picture taken a week after we returned the car (we had the dated receipt). At least they didn’t have us thrown in jail. Yet.
Thanks for the note on the C1 Shopping. I booked a 4 night stay at an IHG hotel in London and it sent me a “congrats” (with the value) email before showing as “Ineligible” in the app. I would be tempted to change the reservation to something else (such as a Preferred Hotel booking), but I think I’ll leave it based on your experience. Most of my IHG stays in C1 Shopping just show as “Pending” rather than “Ineligible,” but I don’t usually book 10 months out either.
Thanks for the heads up on needing to clear security at ACK. I’ll be doing that same 45 min turn in October.
Fingers crossed the lack of delays continues! I’ve done 8 destinations so far with #9-13 scheduled for this weekend and I’ve already had 3 delays of ~2 hours. Luckily, 2 of them were my last flight of the day and the other was before a 7 hour gap between flights for me, so none of them have caused me any stress. My FLL-PHL flight today diverted to JAX for a medical issue and I really wish they’d count JAX for me!
I hadnt flown JetBlue in about 7 years before this challenge and so far I have been very pleasantly surprised at how nice they are. I status matched to Mosaic 2 before starting and I’ve really enjoyed the EvenMore seats and the free wifi on all the planes has been nice as well. Flight attendants have been very friendly on all the flights Ive been on. My only real complaint is that Terminal 5 at JFK desperately needs a renovation and I’m scheduled to be spending quite a bit of time there.
Did you get 150k points after you reached 15 airports and are just waiting for the additional 200k? I read somewhere that those posted quickly after reaching 15 airports and was counting on that!
Unfortunately, no. We only reached #15 last week, but I’ve been hearing the opposite: that points may not post until you finish 25 or the promo period ends.. We’ve not yet received our 150K.
How’s Boston airport #18? Didn’t you fly through it already?
Nope. Departed it several times and we’ve flown into MHT / MVY / HYA and driven to Boston (and to PVD and then flown to NYC), but today is the first time flying into BOS.
I wouldn’t be too sure about this one Nick. Keep an eye on those credit card charges. Happened to me a while ago but I returned a car to Hertz and then they charged me a month later for a 30 day rental despite having rented that car out to other people in the meantime. I’d hope they’d updated things in their system to account for that possibility but it sounds like that may not be the case.
Agreed, as I noted in my comment.
Just not interested
You are interested enough to make a comment.
Great update Nick. I really appreciate you walking us through your thought process.
Thanks for the updates Nick. I had looked at flights and ferries to Martha Vineyard and Nantucket last year and glad to hear you were successful with both.
Adding a data point here for anyone who’s interested. I was told at the Boston Harbor Regency check in that Globalist the breakfast was only covered for two people, but in the end, I wasn’t charged for the two extra adults who stayed in our room and also ate breakfast.
Official Hyatt policy is complimentary breakfast for up to 2 adults and up to 2 children registered to the room, so you were given accurate benefit information. In my general experience at Hyatt properties, we’ve often not been charged when there is an extra adult in the room, but I always expect that I will be and am pleasantly surprised when I am not.
I was hoping to read the part of “How we bought Hyatt points cheaply” within the content, but I don’t see it. Could you point it out? Perhaps I missed it
It was this paragraph (and the photo caption of the rate we paid at the Hyatt Place New York Chelsea:
“As noted in a caption above, I was about to book the Hyatt Leverage rate at this hotel for $175 + tax (about $203 all-in), but then I noticed that the Member Rate was $194 + tax and there was a special rate for $195 + tax that included 3,000 bonus points. That rate with bonus points came to $227 all-in. That seemed like a great deal to me! We’d pay $24 more than the Leverage rate for 3,000 additional points – a cost of 0.8c per point! Our Reasonable Redemption Value for Hyatt points is 1.8c per point, so I was happy to buy at 0.8c. That was a great reminder to me to look at all of the rates, not just the cheapest one.”
I spotted a similar special rate with HP NY Chelsea last month, but I chose a different Hyatt property in the area due to the lower rating at HP NY Chelsea. This opportunity to buy points through a special room rate also has me wanting to remember to look for valuable nightly cash rates.
I did a quick Instagram review of our stay. In short, I thought it was fine. The rooms are small and they certainly told people that the elevators are slow (and I’m sure that they are sometimes, particularly if you’re on a very high floor (where you have to wait for everybody to get off on the way up) or a very low floor (where I suppose you may end up having a few elevators stop that are already full). I would prefer a place with larger rooms, but when the rate here is sub-$200, I’ll probably consider it again.
Is this fun? Because it all sounds like, um, too much.
It sounds like work; something an average person would never realistically do in their free time.
Most of the stuff that we (meaning the collective “we”, as in all of us) do — earning credit card bonuses, maximizing card-linked offers / elite status / promotions, using points for outsized value — is stuff that the average person never does. Obviously some things appeal more to some of us than others, but much of the stuff that you likely do (meaning “you” in general to mean the audience of this site) separates you from “average”. That doesn’t make what you do better or whatever is “average” worse, it just means that different people choose to pursue different things with their free time. The “average” person doesn’t play golf or go snowmobiling or collect baseball cards, but plenty of people do all of those things. Some of them may seem tedious to you and fascinating to someone else. Different strokes for different folks!
For what it’s worth, when JetBlue ran the “All you can Jet” promotion back in 2010/2011, before I knew anything about airline miles or hotel points, my wife and I were already working remotely and we spent the $600 for a month of unlimited JetBlue flights and spent the entire month flying all over the place on JetBlue (with no points or status incentive, just a great price). It didn’t feel like “work” then and it largely doesn’t now — it felt/feels like a fun little adventure. Again, it might not feel that way to you and that’s fine. Part of the reason I write these summary posts is because that 3,000 bonus point rate at a Hyatt Place or the way that our Capital One Shopping rewards went from ineligible to pending or the fact that I was able to use the same link 3 times to get more than $250 total back over several reservations or the experience of cancelling an Etihad booking has nothing to do with whether or not you do the JetBlue 25 for 25 challenge but rather could be useful tips nonetheless. The idea is that you don’t have to be doing the trip or interested in it to take something away from it (though at the same time, none of it may be applicable to you).
For what it’s worth, I’ve run into people in many airports, lounges, and hotels over the past couple of weeks who are doing the 25 for 25 thing, so I guess it does seem like fun to some folks.
Nick-FWIW, I am greatly enjoying following your family’s journey, and I could easily see myself doing something like this just for fun someday (not this particular challenge because the closest JetBlue airport to me is 5 hours away). It’s fun to see how your family is navigating it, even if I do shake my head at your stubborn refusal to get Global Entry for your family (I legit think that’s funny).
I love reading FM trip reports. Whether they’re doing some kind of contest or FM challenge, it’s all interesting to me. I learn a lot from these reports.
I love these reports, and look forward to them – I think your trip sounds like a blast, a cool adventure with your family, since you all (including the kids) seem to enjoy traveling. Keep them coming!
My wife and I did the Bilt Globalist challenge a couple of years ago and she had just retired. It was a blast. I miss Globalist status.