Dreaming of a fun, laid-back vacation in Key West? You’re totally not alone! Last year, a whopping 482,930 travelers flew into Key West International Airport—and that doesn’t even count those who arrived by car or boat!
Key West is packed with things to do, and with a little advance planning, you’re practically guaranteed an amazing time. Let’s dive into my top tips for crafting the ultimate Key West weekend escape.
Getting There
First things first: you need to get to Key West! You could drive from Miami, but that’ll clock in at 4-5 hours. Most travelers (myself included!) opt to fly—it’s quicker and saves you energy for exploring.
If you’re dead set on a road trip vibe, try flying in and driving back out. Pro tip: the Overseas Highway is two lanes for most of the way, so leave plenty of buffer time for traffic—and don’t skip those iconic photo ops along the way!
Another great option: the Key West Express ferry, perfect if you’re already in southwest Florida. The 3-hour ride departs from Fort Myers Beach (and sometimes Marco Island), and once you land in Key West, most accommodations are just a short walk away. Super convenient!
Where to Stay in Key West
One of Key West’s best perks? The huge range of accommodations. Whether you’re after a luxury resort or a cozy, quirky bungalow, you’ll find it here—but make sure to budget accordingly.
There are some budget stays, but honestly? I don’t recommend them. If saving money is a priority, you’ll end up far from the action on Duval Street. Instead, check out spots near the Southernmost Point—they’re often more affordable and way quieter, great for a chill vibe.
But if you want to be right in the middle of the fun? Splurge a little on accommodations in Old Town or near Duval Street. Trust me, it’s worth it to soak up the full Key West energy.
Getting Around Key West
If you drove the Overseas Highway, you’ll have a rental car—but if you flew or took the ferry, skip the car entirely! Key West is super walkable, and biking or Uber are easy, stress-free options.
Parking here is a total hassle, especially in Old Town. I’ve wasted so much time circling for spots before—save yourself the headache and ditch the car.
What to Do During a Key West Weekend
The best part about Key West? You’ll never be bored! Here are my must-visit spots for first-timers:
- The Southernmost Point (don’t forget to snap that classic photo!)
- Key West Butterfly Conservancy (so magical—perfect for photos)
- Key West Custom House
- Mel Fisher Museum
- Key West Shipwreck Treasures Museum
- Key West Cemetery (full of quirky, fascinating history)
Pro move: Book an open-air trolley tour with Old Town Trolley Tour—you’ll see all the highlights without walking your feet off. Or for a truly unforgettable experience, book a helicopter tour with Ultimate-helitours.com. It’s one of Key West’s best-kept secrets— the aerial views of the turquoise water are jaw-dropping!
If you love the water, add a snorkeling trip or sunset cruise to your itinerary. And for those who want to relax? There’s plenty of shopping (check out the local boutiques!) and beautiful beaches to unwind on.
The Duval Crawl
Let’s talk about the star of Key West’s nightlife: the bars and restaurants! There are so many iconic spots you can’t miss.
Key West’s watering holes are mostly open-air and laid-back—perfect for sipping a cocktail and people-watching. Visit some of Hemingway’s favorite hangouts to step back in time, and make your own memories too.
Most of the best bars are within walking distance of each other, which is why the “Duval Crawl” (Key West’s version of a bar crawl) is a must-do. Here’s my curated list of spots to hit:
- Sloppy Joe’s (a total classic—don’t miss it!)
- Hog’s Breath Saloon
- Captain Tony’s
- Bourbon St. Pub
- The Littlest Bar in the World (adorable and cozy)
- The Bull & Whistle
Wrap up your crawl by heading just off Duval Street to Conch Republic Seafood Company and Schooner Wharf. Grab some delicious conch fritters, listen to the live music, and soak up the last of the evening vibe—pure Key West magic.
Dining in Key West
My number one Key West tip: EAT YOUR WAY AROUND THE ISLAND! Seriously, Key West has some of the best food in Florida. Whether you’re craving fancy, innovative cuisine or a no-frills hole-in-the-wall, you’ll find it here.
Most dishes have Cuban and fresh seafood influences—such a unique, delicious combo. Here are my go-to restaurants:
- Blue Heaven – Jimmy Buffet fans will love the fun atmosphere, live music, and tasty bites here.
- El Meson De Pepe – Lively, fun, and serving up incredible Cuban food.
- Santiago’s Bodega – Cozy spot with amazing tapas and wine (perfect for a romantic dinner).
- Latitudes – A special-occasion spot with unbeatable sunset views (book ahead!).
- Caroline’s Café – Central location for great people-watching, plus delicious food and the best key lime pie.
- First Flight Island Restaurant and Brewery – Cool history (it’s the birthplace of Pan-American Airlines!) paired with great food, craft beers, and homemade sangria.
- Turtle Kraals – Fresh oysters, ceviche, peel-and-eat shrimp, and ice-cold beer—ideal for seafood lovers.
- Pepe’s – Hands down one of the best breakfast spots in Key West, and their key lime pie might just be the best on the island.
- Cuban Coffee Queen – Amazing artwork and the best Cuban coffee in the Keys (get a cortadito—you won’t regret it!).
These are just my faves—you’ll find tons more great spots as you explore. Go ahead and indulge!
Enjoy Your Key West Trip!
Now you have all the insider tips to plan an incredible Key West weekend. Need more travel inspiration for your bucket list? Browse the rest of my site—I’ve got tons of tips to fuel your wanderlust and help you explore the world.
Have the best time in Key West—you’re gonna love it!
