DAY 1

Day 1: All Aboard - From LIRR to Liftoff

Our JetBlue 25 for 25 Challenge officially began not with a flight, but with the familiar rumble of the Long Island Rail Road pulling into Jamaica Station. For those unfamiliar with New York's transit ecosystem, the LIRR offers what might be the most convenient and stress-free route to JFK Airport—a hidden gem that many travelers overlook in favor of expensive taxis or ride-shares.

The beauty of taking the train to JFK becomes immediately apparent when you consider that JFK serves as one of JetBlue's three major hubs, alongside Boston (BOS) and Fort Lauderdale (FLL). With JetBlue's extensive operation at JFK, you're virtually guaranteed multiple daily flight options to kick off your challenge, making it an ideal starting point for any serious attempt at the 25 destinations.

Now to start the challenge!

Our first day's itinerary called for JFK → ROC → JFK → SAV->JFK,

a strategic play that would net us three unique destinations (Rochester, JFK and Savannah) while returning us to our New York base for the night. The routing might seem inefficient to casual observers, but in the world of destination collecting, every arrival airport counts toward our tally and since JetBlue is really a hub and spoke (vs. point to point like Southwest), you will find yourself returning to 'home base' often.As an example, to get ROC - the only destination is back to JFK)

The TWA Hotel: A Time Capsule Oasis

Rather than dealing with the hassle of traveling back into Manhattan after our evening return flight, we'd booked a night at the TWA Hotel—one of the most unique airport accommodations in the world. Connected directly to JetBlue's Terminal 5 via the historic TWA Flight Center, this isn't just convenient lodging; it's a masterpiece of mid-century modern architecture that transforms a potential airport inconvenience into a genuine experience.

The convenience factor cannot be overstated. After our final flight of the day, we simply walked through the jet bridge, took an elevator down to the hotel level, and checked in—all without stepping outside or dealing with ground transportation. Our luggage, which we'd strategically stored at the hotel during our day flights, was waiting exactly where we'd left it.

But the TWA Hotel offers something even more valuable than convenience: a genuine escape from the airport environment without actually leaving the airport. The moment you step into the lobby, the noise and chaos of Terminal 5 fades away, replaced by the serene ambiance of the restored TWA terminal with its soaring ceilings and iconic design elements.

Culinary Excellence at 35,000 Feet (Ground Level)

The real revelation, however, was dinner at the hotel's Jean Georges restaurant. Having eaten our share of airport food over the years, we weren't expecting much beyond convenience. What we discovered was a dining experience that not only exceeded every food option available in Terminal 5, but rivaled restaurants in Manhattan's finest hotels.

The Jean Georges menu showcases the chef's signature style while acknowledging its unique airport location with dishes inspired by global destinations—fitting for a restaurant that exists in the constant flow of international travelers. The wine list is sophisticated, the service is impeccable, and the ambiance manages to feel both elevated and relaxed.

Here's a pro tip for future challengers: you don't need to be a hotel guest to enjoy the TWA Hotel's amenities. The restaurant, bar, and observation deck are open to the public, making it an excellent option for extended layovers or when you need a few hours of respite from the gates. During our evening there, we noticed several other travelers who had clearly discovered this secret—business travelers nursing cocktails while working on laptops, families with children enjoying a calm meal away from gate chaos, and what appeared to be other challenge participants comparing notes over dinner.

The hotel's rooftop observation deck deserves special mention. Watching aircraft operations at JFK from this vantage point while sipping a cocktail provides a perspective on aviation that few people ever experience. It's a reminder of the incredible complexity and beauty of the system we're attempting to navigate over the coming months.

As we settled into our uniquely curved TWA Hotel room (designed to echo the terminal's flowing architecture), we reflected on a successful first day. Three destinations checked off our list (22 to go), a comfortable night's rest ahead, and the confidence that comes from a plan executed successfully. Tomorrow would bring new challenges, new destinations, and new adventures, but tonight we were exactly where we needed to be—suspended between the romance of aviation's golden age and the reality of our modern travel marathon.