Weekend getaway to Key West, Florida

While Florida might scream retirees or spring breakers to you, let me pitch Key West as a fun alternative. With its pastel-colored houses, distinctly Carribean vibes, and glorious sunsets, Key West is about as perfect a place for a disconnected weekend getaway you could get without leaving the continental U.S. As the southernmost city of the U.S. just 90 miles from Cuba, Key West has something special going on – it’s found a way to encapsulate the island vibe into a fun playground for creatives, the offbeat, and chickens (yes, chickens, but more on that later!). Once home to Ernest Hemingway, Tennesse Williams and the likes, Key West used to be something of a hotspot for the creative elite – it has been said to have inspired more writers per capita than any other American city. Today it’s more Duval-street-debauchery, a mile-long pub crawl fueled by cheap drinks and a desire to just let it all go while listening to live music and dancing the night away. Really, it could be a lot, lot worse.

As for the chickens…well apparently it’s a thing. My friend remarked when I was there it was weird we constantly heard roosters crowing. I didn’t think anything of it then but apparently, there is an unreasonably large number of chickens in Key West, so much so that the Key West Wildlife Center has a special program for the rehabilitation of stray chickens. So weird, but hey Key West is weird.

How to get to Key West

You essentially have 3 options:

  1. Get a flight to the Key West airport.
  2. Get a flight into Miami and drive there down the Overseas Highway, a one-lane highway for the most part (it’s about 3 hours without traffic). You go through the scenic 7-mile bridge which is especially beautiful during sunset.
  3. Get a ferry from Sarasota, Florida.

When to go to Key West

As expected, the weather is hot and humid here all year long. Some would tell you not to go to Key West during the hurricane season between June and November. I have been there in June twice. Usually, you have to deal with some afternoon showers but that’s about it. All in all, not too bad except be forewarned that the streets flood quite easily. My recent trip was on Pride weekend which is always a fun and unique time to visit. Key West has a long history of being a welcoming community for all sorts of people from different places and backgrounds, including the LGBTQ community.

Where to stay in Key West

We stayed at the quaint Duval Inn, online it doesn’t look like anything much, but in fact, it was the perfect place to stay and quite affordable by Key West standards. With cozy, well-appointed rooms, a nice pool and a quirky poolside bar and garden, it’s also perfectly located just a block from Duval Street making everything easily accessible on the island.



What to do in Key West

The first thing you need to understand about planning a trip to Key West is that it is ridiculous – you have no business planning every minute of your trip. Key West is the kind of place where you let it go and go with the flow. If that’s not you in real life, well then don’t plan to move to Key West any time soon. Just visit and use this as an opportunity to disconnect, slow down and reconnect. Check out my tips on the best ways to be mindful when traveling if you could use a few pointers.

My list of things to do in Key West is intentionally broad so you can follow the spirit of it but do what makes you happy that morning when you wake up.

Walk around and enjoy your surroundings

Just 8 square miles, Key West is a walker’s paradise, even for those who might not usually enjoy it. Duval Street is a mile-long and interspersed with cute, local stores amongst bars. Venture off Duval to see what else Duval has to offer – really at 8 square miles, you have no excuse!



Try some water sports

You can’t go to an island and not get in the water! Moreover, living on the west coast, I have come to appreciate the warm Gulf waters compared to the perennially freezing Pacific. Just get in the water, will ya?! We did a dolphin spotting and snorkeling tour with Barefoot Billy’s that we really enjoyed. The group was small enough that we felt well taken care of and the crew was knowledgeable and friendly. Key West has the third largest coral reef after Australia and Belize, so it’s worth the trip! Barefoot Billy’s also offers jet ski and sunset tours which we would have taken advantage of if we had more time.



Catch the infamous Key West sunset

It’s infamous for a reason, I’ll say that. Even on cloudy, rainy evenings, the sunset was stunning to witness; the sky drenched in saturated shades of oranges, pinks, and yellows. Mallory Square is the most popular place to catch the sunset and it comes to life around that time. Be sure to catch some live music and dancing at the fun Cuban restaurant, El Meson De Pepe.



Another option is to watch it while having mojitos and listening to live music at Sunset Pier, aptly named.


This is the kind of thing where pictures tell better stories than words, so check out a few!






Enjoy the nightlife

Let’s face it, Key West is a bachelorette party hotspot for a reason but even if you are not in the mood to get rowdy, Duval Street is a fun place to hang out and listen to live music. We heard what had to be one of our all-time favorite live music performances at Sloppy Joe’s. Willie T’s is another fun spot with an outdoor patio and local musicians. El Meson De Pepe and Sunset Pier are also great as I mentioned before.

If you are in the mood for more dancing and revelry, Fat Tuesday’s and Rick’s are fun places to go.

Fuel up in between drinks at umpteen pizza spots along the way. In fact, as a vegetarian, I am not enamored by much of the food on the island, and the quality is not that good or the prices you pay. So I prefer to have smaller meals throughout the day, stopping into the nearest spot tucked in between bars.

Enjoy the Carribean vibes

You are about as close to being on a Carribean Island without leaving the continental U.S. so enjoy it! From towering palm trees to candy-colored conch houses to a distinctly bohemian vibe, Key West just screams the Carribean, way more than any city I have been to in the U.S. If you want a more literal Carribean experience, head to Bahamian Village Market and sample some authentic Bahamian food while swaying to Bob Marley-esque tunes.




All in all, make your getaway to Key West truly that- a getaway – a chance to eat some delicious key lime pie and swelter in the humidity while getting swept up by the laid-back island vibes.