This was the second, and final, two-night trip that my wife, Sharon, is going to be doing for JetBlue’s 25-for-25 promotion. I had this one booked before her first set of flights, but after that experience she made it clear that one night away from home was her limit.
So, after this trip, I planned the rest of her flights as single-night itineraries (like Nantucket and Detroit) and a few one-day out-and-back runs to finish the challenge.
When this trip started, she was sitting at 14 destinations — meaning the next one would bring Sharon to airport #15 and unlock the 150,000 TrueBlue point milestone.
Day 1: Orlando – Islip – JFK – Buffalo
The first flight of the trip was from Orlando (MCO) to Islip, Long Island (ISP). It’s one of those airports that primarily connect back to Florida cities on JetBlue. Since there are no onward JetBlue flights from Islip, I built in a transfer via the Long Island Rail Road (LIRR) — about an hour from Ronkonkoma to Jamaica Station, then a quick AirTrain ride to JFK.
Not wanting to cut it close, I left several hours between flights. That turned out to be a good move, because Sharon’s flight had to return to the gate in Orlando due to a passenger disruption and was later delayed by a weather ground stop. Even with those hiccups, she made it to the train station with time to spare and arrived at JFK in time for her next flight — though there wasn’t much opportunity for food or a bagel.
The evening flight was from JFK to Buffalo (BUF), a short hop across New York. After landing, Sharon headed to the Courtyard by Marriott, along with the crew from her JetBlue flight. The on-site restaurant was still open, so she grabbed a quick bite to enjoy in her room before turning in for an early morning departure.
Now that she’s visited several Courtyards, her comment about them to me was, “All Courtyards look alike.” I explained that was what people liked about them.
Day 2: Buffalo – Boston – Raleigh – Boston
The next morning started bright and early with a 7 a.m. departure to Boston (BOS). The good news was that Sharon had a long enough layover to relax — more than two hours — and headed straight to the Chase Sapphire Lounge.
To my surprise, Sharon has really come to like this lounge — even more than the Centurion Lounges we’ve visited. She says the breakfast is actually good, which is probably true, but might also be because it was the first proper meal she’d had in almost 24 hours.
From Boston, she flew to Raleigh-Durham (RDU) and back — an easy out-and-back pairing I could fit in the same day. While many of her recent flights have been on JetBlue’s newer A220s, this one was on a much older A320 that’s seen better days.
While at RDU, she experienced her first delay caused by the government shutdown, as air traffic into Boston was restricted. Luckily, I’d built plenty of buffer into the schedule, and she still made it back to Boston by mid-afternoon.
For the overnight, I booked the Hilton Boston Logan Airport. Two days before the stay, she received an email upgrade notification — thanks to her Hilton Gold status, she’d been moved to a corner room on a high floor.
After finding the shuttle stop (and realizing that, despite what “ChatGPT directions” told her, you need to call for the hotel shuttle) she headed to the hotel. The upgraded room turned out to have a sweeping city view — not bad for a night’s stay before an early flight.
Day 3: Boston – Norfolk – Orlando
On the final morning, Sharon enjoyed what qualifies as a “late” departure in this challenge — 7:30 a.m. I hate scheduling these early flights, but they’re often the only way to make the connections work. Fortunately, this was an easier day and the last leg before heading home.
The first flight was Boston (BOS) to Norfolk (ORF), one of JetBlue’s seasonal routes. It worked perfectly as a midway stop en route to Florida. Since JetBlue doesn’t operate Norfolk–Orlando, I booked her on a Southwest flight to finish the trip.
And for once, the travel gods were smiling — one of the twelve open seats on the flight happened to be the middle seat in her row.
She was home by 2 p.m. and ready for a well-earned nap. With Norfolk added, Sharon’s now up to 18 total airports — more than two-thirds of the way to the 25-for-25 goal.
What We’ve Learned So Far
This promo has been as much about patience as planning. For starters, there’s no tracker or progress page. You’re completely on your own to keep count of how many airports you’ve visited. I’d expected to see some acknowledgment once Sharon hit 15 destinations and qualified for the 150,000-point bonus, but based on what others are sharing on Reddit, that’s not how JetBlue is handling it.
Apparently, participants will receive their milestone bonuses — for 15, 20, and 25 airports — either at the end of the year when the promotion closes or all at once after reaching 25 airports.
It’s a bit of a letdown if you were hoping to use those earlier miles to offset later flights, but that’s part of the adventure. It’s a mix of logistics, timing, and a little bit of trust that JetBlue’s tracking everything correctly behind the scenes.
Running Total
Airports completed: 18
Flights taken: 24
Hotels stayed: 6 (Drury ATL, Residence Inn JFK, Cliff Lodge Nantucket, Westin Detroit, Courtyard Buffalo, Hilton Boston Logan)
Train rides: 3 (two Brightline, one LIRR)
Bus rides: 1 (MHT – BOS)
Lounges visited: 2 (Plaza Premium MCO, Chase Sapphire BOS)
NY bagels consumed: 3, and counting
Final Thought
With just seven airports to go, the finish line is in sight. Sharon’s handled ground stops, delays, early mornings, and late nights with impressive patience.
The JetBlue 25-for-25 challenge has been part travel puzzle and part endurance test. If everything stays on schedule, she’ll be crossing the finish line before Thanksgiving with 350,000 TrueBlue points and 25 years of Mosaic status to show for it.
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