Off-time Adventures: Key West, Florida

A whirlwind weekend away, a varied non-rev experience, and some obligatory beautiful blue water pictures. It’s time for an off-time adventures recap from Key West!

First and Not Least: Non-Rev Success

Sometimes non-reving works exactly like it’s supposed to. Flawless connections, no bumps, first class. On the way down I wasn’t sure I would make it to Key West at all. Flights were overbooked by the time I got to the airport [for reference, I flew PHL > CLT > EYW]. But that’s the thing about non-reving—you have to show up to have a shot. CP was already in Key West and we planned for a long shot in the event that I could make it down. I arrived at the gate and a miracle of all miracles happened [for me anyway]. A flight from Toronto arrived late and 10 seats opened up on the flight. One hurdle was cleared, but what if I got stuck in Charlotte? All I can say is I that got lucky, and had a backup plan. I have a friend in the city and had I not made the connection, my plan was to grab dinner with him and fly back to Philly that night.

Pro tip: If you can, book between hubs to have the greatest number of flight options. If all else fails, plan ahead for how you’ll kill time.

But I made the next flight too and landed in the Keys in the early afternoon.

How to spend 24 hours in Key West

Key West is a really lovely long weekend escape if you like a little beach, a little heat, and a lot of people watching. In total, I actually only spent about 20 hours on the ground [outside of my airport attempts, which we’ll get to]. If you’ve got a day to spend, below are my picks for how to spend it:

Grab Lunch at Santiago’s Bodega

For those of you familiar with the concept of a bodega, it’s actually a restaurant. And a good one! It has an extensive wine and beer list, good happy hour specials, and their tapa menu is great. Also, when they say the salads will feed three to four people, they mean it.

Take In The Colorful Colonial Houses

Key West architecture is pretty and peculiar. It has one foot in Caribbean living with colorful store and home fronts, and one foot in old school Americana with big Colonial homes preserved from the 50-60s. Stroll a neighborhood street and take it all in.

Pop In For A Drink At Green Parrot

A long-time favorite of many visitors for a reason. Relaxed ambiance, live music on the weekends, and on a long line of other good bars to do a bar crawl.

Sail The Sunset On A Catamaran

It’s fun, romantic, and a little [lot] boozy. Orange skies over blue water with cool night air? Sign me up.

Bar Crawl Down Duval Street

It’s an eclectic mix of hole-in-the-wall bars and upscale restaurants with outdoor spaces, and there is no better place to wrap up a night people watching.

Non-Rev Snags

Nothing goes as planned. Flawless way down, very flawed return. It’s the flip side to the amazing perk of being to fly anywhere on the cheap or free: sometimes you get stuck. I spent the day in the tropical Key West airport being bumped from flight after flight trying to get off the island [ 4 total attempts, 1 success]. My original plan was to fly EYW > MIA > PHL. But everyone with a confirmed ticket had the same plan. [Ultimately, I went west to go north and flew EYW > DFW > EWR and had an airport pickup to go back to Philly with CP]. I landed in DFW and was immediately cleared for my connection [no small celebration]. 14 hours after I arrived at the airport that morning, I landed in Jersey, which given other experiences I’ve had, was not so bad. I count any non-rev trip where you land where you intended in the same day as your first attempt a success.

So overall, a good time, not a long time, and would recommend for a weekend away.