Back in June, I wrote about JetBlue’s 25 for 25 promotion, which offers 350,000 TrueBlue points and 25 years of Mosaic status if you can fly to 25 different airports within a set timeframe. At the time, I went back and forth on whether it was worth it (spoiler: I wasn’t entirely convinced).
But while I wasn’t planning to push myself into chasing it, my wife Sharon surprised me by saying she really wanted to give it a go. Who was I to stop her?
That left me with the job of logistics manager: figuring out how to get Sharon to 25 different airports on JetBlue flights. Orlando is a solid starting point with plenty of JetBlue service, but most routes are point-to-point. For example, you can fly from Orlando to Albany, but then your only option is usually to head back to Florida. Only a handful of cities connect directly to JetBlue’s big hubs at Boston (BOS) and New York (JFK), which are the linchpins in making this work.
Caribbean flights were tempting, but we ruled them out to avoid immigration hassles and potential overnight stays. That meant keeping the first run strictly domestic.
After three days on the road, Sharon managed to check off 7 airports — not a bad start. Here’s how the first leg played out.
Day 1: Orlando – Richmond – Boston – Atlanta
Sharon’s journey began at the Plaza Premium Lounge in Orlando’s Terminal C, a spot she’ll be seeing a lot of during this promo.
The first leg was Orlando (MCO) → Richmond (RIC), a smart “bridge” airport on the way to the Northeast. She lucked out with JetBlue’s retro-inspired “What’s Old is Blue Again” livery, which was a fun way to kick things off.
From Richmond, she connected to Boston Logan (BOS), one of JetBlue’s major hubs, on a comfortable Airbus A220. She managed to make a stop at the Chase Sapphire Lounge before heading to the next flight.
This was Sharon’s first experience at Boston airport and she quickly learned that you’ll get in your steps going from gate to gate.
Her final flight of the day backtracked south to Atlanta (ATL), which doubled as her first overnight stop. While ATL has hotels connected to the SkyTrain, they were fully booked. Instead, I booked the Drury Inn Atlanta Airport. I’ve stayed with Drury before, but this was Sharon’s first experience — they’re not fancy, but they’re dependable, and that’s what mattered after a long day.
Day 2: Atlanta – New York (JFK) – Jacksonville – New York (JFK)
Day two started bright and early with a 7 a.m. departure from ATL. Breakfast was McDonald’s on the go before heading to New York JFK, another key JetBlue hub.
JFK’s JetBlue terminal doesn’t have a lounge, but Sharon made up for it with a classic NYC bagel — and yes, even an airport bagel beats what we can get at home.
By mid-morning, she was already boarding her second flight of the day: JFK → Jacksonville, FL (JAX). Jacksonville is one of those oddball airports you can really only reach from the Northeast, so it was important to check it off.
After a quick turnaround, she boarded the same A220 back to JFK, wrapping up her flying by mid-afternoon.
For the overnight, hotel options near JFK were limited. The TWA Hotel is iconic but outrageously expensive, and the Hyatt Regency requires a rideshare without a shuttle. Instead, Sharon stayed at the Residence Inn near JFK, which has earned solid reviews and was a step up from the Courtyard where we stayed years ago (and vowed never to return).
Day 3: New York (JFK) – Charleston – New York (JFK) – Fort Lauderdale – Orlando
The final day started with another out-and-back trip, this time to Charleston, SC (CHS). After a short stop, she was back at JFK — and yes, she squeezed in another bagel before her last flight of the day.
Instead of flying directly home to Orlando, she routed through Fort Lauderdale (FLL). With so many Florida airports on JetBlue’s map, we’ll need to use them strategically to reach 25 unique airports. From there, she hopped on the Brightline train for the final leg to Orlando.
I picked her up from the Brightline Orlando station at 10 p.m., wrapping up three packed days: 9 flights, 2 hotels, 2 bagels, and one Brightline train ride.
That brings Sharon’s total to 7 airports completed — only 18 more to go.
Final Thought
This first run highlighted both the fun and the frustration of chasing JetBlue’s 25-for-25 challenge. Sharon got to fly on a special retro livery, sample bagels at JFK, and knock out a healthy 7 airports in just three days. On the other hand, hotel options (especially at JFK and ATL) and the need for careful routing made it clear this isn’t a casual undertaking.
Still, the promo’s prize is one of the most lucrative I’ve seen in years. With 350,000 TrueBlue points and 25 years of Mosaic status on the line, the adventure is just beginning — and we’ll be sharing updates along the way as Sharon inches closer to that magic number.
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2 comments
Dont understand Day 3 why did she fly back to JFK from CHS she already had JFK covered, instead she should have stayed overnight @ CHS and flown the next morning to FLL. Hotels are cheap $ and pts wise by CHS. Even better spend the day walking around CHS its a GREAT walking city. The cost might have been cheaper as well for the Hotel over the flight(of cause some days the fare is out of wack but usually not)
I thought I messed up for a second but, as you see, the direct flight from CHS to FLL only departs in the morning, after her flight arrived. So it would have meant another night in a hotel in CHS. We’re focusing on doing this on as little time away as possible, so it did mean one more flight but she got home the same day.