After my wife’s first three-day sprint knocked out 7 airports, she asked if future runs could be limited to one night away from home instead of multi-day marathons. Fair enough! That added a new twist: how do we maximize new airports while mostly starting each run via JFK or BOS? I asked if she’d be willing to take two short trips in one week—Monday to Tuesday and Friday to Saturday—and she agreed.
With each itinerary, I’m getting better at reading JetBlue’s schedule quirks and uncovering city pairs I didn’t even know existed. That tinkering is how the Nantucket idea popped up. (If you missed how this whole thing started, here’s where I went back and forth on whether the promo was worth it, and here’s Part 1 with the first 7 airports.)
Trip 2: Orlando – Washington D.C. (DCA) – Nantucket (ACK) – White Plains (HPN) – Orlando
Nantucket (ACK) has several seasonal JetBlue routes. Besides the usual JFK/BOS options, there are flights to LGA, DCA, and HPN (White Plains). JetBlue also partners with Cape Air for other New England hops, but those don’t count toward 25-for-25.
Conveniently, JetBlue flies nonstop from Orlando to both DCA and HPN—two airports we still needed to visit. So I stitched together an overnight sequence that would tick three boxes at once: MCO → DCA → ACK → HPN → MCO.
The only downside was a 4+ hour layover at HPN before the flight home. Not glamorous, but this challenge isn’t about glamour—it’s about knocking out airports.
Once I knew Sharon would overnight on Nantucket, I had to find a hotel. Spoiler: There are no major chains on the island. A few Mr & Mrs Smith properties are bookable with a ton of Hyatt points, but that didn’t make sense for one night.
Instead, I found a charming option at the Cliff Lodge—a quaint inn within walking distance of the port and plenty of restaurants. Perfect for a short stay and very “Nantucket.”
On the way home, Sharon almost made an earlier HPN→MCO departure—she was at the gate before the door closed—but the flight was already sealed. Perhaps Mosaic flexibility will aid in moves like that later in the journey.
Trip 3: Orlando – Manchester (MHT) – Boston (bus) – Detroit (DTW) – New York (JFK) – Palm Beach (PBI) – Orlando
The weekend run wasn’t as scenic, but it was a fun logistical puzzle. Instead of flying to Boston, Sharon went MCO → MHT and then took a bus to Boston Logan. With a nice buffer before her next flight, she grabbed dinner at a local classic:
The evening hop was BOS → DTW. With a 6:00 a.m. flight the next morning, I booked a room at the Westin Detroit Airport. It wasn’t as convenient as I’d hoped—JetBlue operates from a different terminal than the hotel’s private TSA checkpoint—but the frequent airport shuttle (about every 10 minutes, 24/7) made it easy. (Note from Sharon: being at the “wrong” terminal was a moot point…I arrived at DTW long after the private TSA checkpoint was closed for the night, and left hours before it opened).
At dawn, Sharon flew DTW → JFK (yes, another NYC bagel stop), then continued to PBI—another Florida airport we needed to check off—before taking the Brightline train back to Orlando.
Running Total
- Airports completed: 14 (more than halfway to the required 25)
- Flights taken: 17
- Hotels stayed: 4 (Drury ATL, Residence Inn JFK, Cliff Lodge on Nantucket, Westin Detroit)
- Brightline rides: 2
- NY bagels consumed: 3
At 15 airports, Sharon will cross the promo’s first points milestone: 150,000 TrueBlue points. She’s also earned 14 Tiles, which pushed her past the 10-Tile threshold for an extra 5,000-point bonus. And we picked up the JetBlue Business Card—so once we hit the spend requirement, there’s another bonus coming, plus extra points for every JetBlue flight we pay for with the card.
Final Thought
Flights are already booked to take Sharon to 24 airports. I’m leaving the last slot open—partly as a buffer in case IRROPS throws a wrench into the plan, and partly so we can make that final flight a little special (Note from Sharon: HE wants to make it special. After what will be 24 flights by that point, *I* just want to make it as short of a flight as possible and be done with it).
So far, this has been equal parts logistics puzzle, mileage run, and quirky adventure. From cozy Nantucket inns to airport shuttles at midnight and Brightline rides home, every segment gets her closer to the finish line. Onward to 25!
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