A weekend in Key West is a great escape from anywhere, but especially if you already happen to find yourself in South Florida. (First of the Key West tips: add on a weekend here to any South Florida vacation.)
Key West, Florida has its own international airport which is definitely the fastest and most direct way to get there (with amazing island views). You can get to EYW on American Airlines, Delta, Silver Airways, and United. You can even fly direct to Key West from cities like Atlanta, Dallas, Charlotte, Philadelphia, and most major Florida airports.
Alternatively, Key West is only a 3.5-hour drive from Miami and just 15 minutes longer from Ft. Lauderdale. Plus, you get to drive over the seven mile bridge which is an experience in and of itself.
A weekend in Key West
The great thing about Key West is that there’s enough to do to keep you busy all weekend. But there are also enough ways to just chill out and *do* nothing. For whichever travel style floats your flamingo-shaped boat, Hotels.com and I have teamed up to bring you this list of Key West tips for your weekend in the Conch Republic. But first…
Where to stay during your weekend in Key West
Key West is a chill little island so your lodging should be just as chill. Mega resorts and huge hotels are not the Key West way. Instead, check out these highly-rated hotels for a lovely little getaway – all have at least a 9/10 rating from past reviewers!
Here are some options for great places to stay in Key West:
Barbary Beach House Key West
I love this property for its clean look and its location across the street from Smathers Beach. I know, I know… Key West is not really a “beach” town, but I’m still the kind of tourist who wants her Florida to come with a little sand.
But one of the most popular ammenties to this hotel is their free area shuttle that’ll get you to over to Duval Street in a jiffy. Check out the Barbary Beach House here.
Orchid Key Inn
Another adorable little hotel with a great Old Florida vibe is the Orchid Key Inn conveniently located in Key West’s Old Town near Duval Street.
This hotel has a 9.8/10 rating and reviewers love it for:
- Its location in the best part of Key West
- The friendly and accommodating staff
- The clean and well-maintained property
- And much more!
Check out the Orchid Key Inn here.
If you want more of a chill, local vibe, definitely check out the Weatherstation Inn, an adults-only bed & breakfast near Duval Street.
Staying here will have you feeling like you just moved to Key West as this place is super homey. It comes with free WiFi, free parking, and free cancellation. It’s small (only 8 rooms), comfortable, and much quieter than staying in a traditional hotel. Plus, you can’t beat the location. Check out the Weatherstation Inn here.
Key West safety tips
Navigating travel right now is still a tricky situation. If you do decide to take a trip to Key West sometime soon, please do so as responsibly as possible. Remember to always wear a face mask, wash your hands regularly and use hand sanitizer, and maintain a 6-foot distance from others at all times.
Always check official websites before your trip for the latest updates on local and national policies, mandates, and regulations. (And it never hurts to book accommodation with free cancellation in case your plans change unexpectedly.)
Key West tips for sightseeing
When it comes to sightseeing in Key West, you can do as little or as much as you want. But however much you do, make sure to do it the smart way. Here are some Key West tips for sightseeing on the island.
Getting your picture taken with the Southernmost Point buoy is probably the most popular “must-do” thing in Key West, Florida. And because of this, that means long, long lines. Yes, even though all the pictures you see of it make it appear as if you’re the only one there. #expectationvsreality
Key West tip: Head there first thing in the morning (I’m talking sunrise, people!) to avoid having to waste your weekend in a super long line (in the sun) just for a photo op. Besides, it’s not even the southernmost part of the country. Have we forgotten about Hawaii so soon?
Another of the most popular things to do in Key West is a visit to the Hemingway House – the former residence of author Ernest Hemingway from 1931-1939.
At the Hemingway House you can tour the bedrooms and writing studio, the gardens and pool area, and more. But one of the most interesting parts of a visit here is actually the current residents.
Key West tip: The Hemingway House is loaded up with cats. But these are a unique kind of cat that descends from Hemingway’s personal pet Snow White. While there, be sure to look at all the cats’ feet. These polydactyl cats all have six (and even 7) toes on each paw.
Today, 6-toed cats are actually known worldwide as “Hemingway Cats.” This whole time we’ve been afraid that all it would take for cats to take over the world was opposable thumbs. We’re actually not that far off. Consider yourself warned.
Old Town Trolley Tour
Chances are you’ll see these green and orange trolleys toot-tooting all around Key West. And while they may seem like a great way to see some of the sights and get around town without a lot of walking, know they’re not all that and a bag of plantain chips.
They’re not the worst tours you can take, but the cost is high and the value isn’t exactly where it should be.
Key West tip: Before you book the Key West Old Town Trolley Tour, check out my review of my recent Old Town Trolley Tour in St. Augustine to see what they’re all about and if it’s really right for you.
Free things to do in Key West
Because of its remote location and limited availability of just about everything (except rum—there’s plenty of rum), a weekend in Key West isn’t exactly the most budget-friendly destination.
However, there are still plenty of ways to get your Caribbean jollies without going broke. Key West tip: save some cash by checking out a few of the free things you can do in Key West:
Key West Cemetery
Yes, you should visit the cemetery. Visiting cemeteries is actually something I do on quite a few of my trips, for one reason or another. But why this one? I’ll get to that in just a short scroll.
The beach is completely free to access and there’s a free parking lot a short walk away for when you just gotta feel the sand between your toes. (A side effect of all the rum methinks.)
Florida Keys Eco-Discovery Center
Learn all about the plant and wildlife of the Florida Keys in these 6,000 square feet of exhibit space. There’s a 2,500-gallon reef tank with tropical fish, an exhibit on Aquarius, the only underwater ocean lab in the world, and many other informative displays and cute animals.
Admission to and parking at the Florida Keys Eco-Discovery Center are always free!
Key West Wildlife Center
The Key West Wildlife Center is a non-profit wildlife rescue center that rehabs and eventually (if all goes well) releases animals back into the wild—with a focus on native birds.
You can visit the Wildlife Center and meet a couple of their animal ambassadors, walk the nature trails, and learn about local wildlife. Admission is free (but donations are appreciated).
Key West tips for eating and drinking
Eating and, okay, especially drinking are a big part of the Key West experience. The list of places to go and things to eat is wicked, wicked long so I’ve narrowed it down to this short list of Key West tips.
Sloppy Joe’s is arguably the most famous bar in Key West, named for Hemingway’s prohibition booze-toting buddy Joe Russel. Known for its live music, its atmosphere, and for being a one-time Hemingway hangout. However, if you can, plan your trip around this one certain event.
Key West tip: If your schedule allows for it, plan your trip to Key West for late July when Sloppy Joe’s holds their annual Ernest Hemingway Look Alike Contest. I first heard about this event after Adventurous Kate’s visit and I have a hard time believing it’s not the most fun you’ll have in Key West.
Key lime pie
Not surprisingly, key lime pie is the specialty here in Key West. And you can find it everywhere. (Hallelujah!) However, know that not all slices are created equal. If you have limited stomach real estate, be choosy about where you get it.
Key West tip: Start your search for the world’s best key lime pie at these places:
- Key Lime Pie Bakery for their coconut key lime pie (Anything with the word ‘coconut’ in it has my attention.)
- Blue Heaven for meringue lovers
- Kermit’s Key West Key Lime Shoppe for a classically delicious key lime pie.
I’m a huge fan of Cuban food and one of the best things about Key West is that its only 90 miles from Cuba. To put this into perspective, the nearest Walmart is 130 miles away.
Key West tip: When in Key West, be sure to embrace Cuban culture with some amazing Cuban food. Some of the most highly rated spots include:
- Cuban Coffee Queen
- El Siboney
- El Meson de Pepe
Key West tips for unique things to do
Key West, Florida is without a doubt a colorful destination, in every sense of the word. And while you can definitely get a taste of that on Duval Street or at one of Key West’s famous drag shows (look to 801 Bourbon, Aqua, or La Te Da for those), Key West’s character can be found in many other places.
Nancy Forrester’s Secret Garden
Nancy Forrester is a local teacher and environmental activist who’s been rescuing and re-homing orphaned parrots for over three decades. (#adoptdontshop) She invites visitors into her bird sanctuary to interact with and learn about these awesome and incredibly intelligent birds.
Key West Cemetery
For whatever reason, I always find myself visiting cemeteries when I travel. Not many of them are this funny though.
The Key West Cemetery is known for being a little bit different in that Key West residents are known for taking their senses of humor to the grave. Key West tip: look closely at the headstones for a little LOL. The most famous being that of B.P. Roberts whose headstone reads “I told you I was sick.”
Key West wild chickens
Much like the wild chickens of Ybor City in Tampa, Key West also has a community of wild chickens and roosters running amok. These birds are descendants of the ones bred in Cuba and raised here for fighting. Once the “sport” was made illegal, the birds were released and have led a feral existence ever since.
The locals and the freebirds may have a love/hate relationship, but seeing these beautiful wild chickens running around the city is always a treat for visitors.
I hope this quick guide to Key West tips has helped get you started for your weekend in Key West! Have a fun and totally chill time down there.
More info for your weekend in Key West
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