TL;DR: Leg 5 of my JetBlue 25 for 25 challenge was a one-day sprint through five destinations. I racked up 1,280 miles, spent 5h 27m in the air, and added $371.27. Highlights included a plane full of fellow challengers on the way to Martha’s Vineyard, turning a picnic bench into an office (with a quick swingset break), and hitting destination 25 in Atlanta, where a canceled flight turned into the perfect finale with an even earlier ride home.
Day 1: Washington (DCA) > Boston (BOS) > Martha’s Vineyard (MVY) > New York (JFK) > Atlanta (ATL) > Washington (DCA)
Leg 5 started the same way most of these have: with me glaring at the DC Metro schedule and resigning myself to yet another early morning Uber. And again, I wasn’t even flying JetBlue out of DCA. I booked a dirt-cheap American Airlines hop to Boston, and wouldn’t you know it, they upgraded me again. American is basically that toxic ex who keeps sending flowers even though you’ve moved on.
I grabbed a quick breakfast in the lounge at BOS before continuing on to Martha’s Vineyard. The plane was practically empty — maybe 45 people total — but when the flight attendant asked who was doing the challenge, nearly everyone raised their hand. Suddenly, half the plane was laughing together, comparing notes, and trading stories. It felt like a weird little mileage-run summer camp. Most people were still on their early legs, while I casually mentioned I was closing in on my 24th and 25th. Definitely a highlight of the whole challenge.
On the ground at MVY, I had a couple of hours to kill. So naturally, I sat at a picnic bench with my laptop like the world’s least glamorous digital nomad. And then, because apparently I regress under island air, I wandered over to a swingset and actually went for a swing. A grown adult in the middle of a frequent flyer challenge, pumping my legs on a playground swing. Honestly? Pretty great. (There were no children present).
From there it was back to JFK, which meant another round of the “exit security, take the train, re-enter security” routine. I hit the lounge, ate, worked, repeated the cycle, and eventually boarded my flight to Atlanta. This was supposed to be it. Destination 25. The big finish. Everything was going smoothly, too smoothly.
Cue the chaos. Midway through the flight, I got the dreaded email: my Atlanta–DCA connection was canceled. A $47 American Airlines ticket had evaporated, and they “helpfully” rebooked me for the next morning. Which would’ve been fine if I’d packed clothes. Spoiler: I had not. A lot of people would call that a disaster. I called it great storytelling.
Once I landed, I tried the polite approach with an American gate agent. They shrugged. Weather cancellation meant no obligation to help. Panic creeping in, I decided to try another agent and gave them the same spiel. This time, jackpot. He rebooked me on a Delta flight to DCA leaving in about 20 minutes. Problem solved, plot twist preserved.
Naturally, I still took the train to the lounge, wolfed down some dinner, and hustled to my gate just in time to board. I landed back at DCA earlier than I would have on my original ticket, grabbed an Uber home, and called it a night.
And that was it. Leg 5. Destination 25. The perfect, messy, exciting finale to the JetBlue 25 challenge.
Stats
| Airports Visited | 5 |
| Unique Destinations | 2 |
| Segments (Individual Flights) | 5 |
| Newest Aircraft Age | 1 |
| Oldest Aircraft Age | 24 |
| On and Off the Same Airplane | 0 |
| Aisle Seat Count | 3 |
| Middle Seat Count | 0 |
| Window Seat Leg | 2 |
| Total Distance (miles) | 1,280 |
| Total Time (Air + Taxi) | 7:46 |
| Total Air Time | 5:27 |
| Time Saved (Early Flights) | 1:01 |
| Time Lost (Delayed Flights) | 0:17 |
| Times Through Security | 4 |
| Times Randomly Selected | 0 |
| Times Bag Pulled | 0 |
| Lounge Visited | 3 |
Costs
| Planned | Actual | Difference | |
| jetBlue Flights | $276.18 | $276.18 | +/-$0.00 |
| Other Costs | $102.99 | $95.09 | -$7.00 |
| Total | $378.27 | $371.27 | -$7.00 |
| Avg | $189.14 | $185.64 | -$3.50 |