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Key West Weekend Getaway

How to Have the Ultimate Key West Weekend Getaway

Are you dreaming of a fun and relaxing vacation in Key West? You’re not alone! In fact, a whopping 482,930 people flew into Key West International Airport last year – and that doesn’t include the tourists that arrived by car and boat! 

There are a ton of things to do in Key West, and, if you plan ahead, you’re almost guaranteed to enjoy an amazing time! Start with these hot tips for planning the ultimate Key West weekend.

Getting There

Before you can enjoy your time in Key West, you need to get there! You could drive from Miami, but that will likely take you four to five hours. Most people prefer to fly.

If you really want to experience the road trip, consider flying in and then driving back out. Just remember, it’s a two-lane highway most of the way, so leave plenty of time for traffic – and a few strategic photo stops.

You can also take the Key West Express ferry if you’re already going to be in southwest Florida. This three-hour trip departs from Fort Myers Beach and sometimes from Marco Island. When it arrives in Key West, it’s just a short walk to most accommodations.

Where to Stay in Key West

One of the things that makes Key West so great is the wide range of accommodations available. Whether you want to stay in a high-end resort or a quaint bungalow, you can find what you’re looking for here. You’ll want to make sure you budget appropriately, though.

While there are some cheap places to stay in Key West, we wouldn’t recommend them! If saving money is important to you, then you’ll end up a way off from the popular Duvall Street. Accommodations near the Southernmost Point are often less expensive, and the area is much quieter.

However, if you want to be in the middle of all the action, then try to set aside some extra money for your accommodations. This will ensure you get the full Key West experience.

Getting Around Key West

If you’re driving the Overseas Highway, then you’ll probably already have a rental car. However, if you arrive by plane or boat, we recommend skipping the car altogether. In Key West, it’s easy to travel by foot, on a bicycle, or in an Uber.

Parking in Key West is often a hassle, especially if you’re staying in Old Town. This is another reason to reconsider driving.

What to Do During a Key West Weekend

When you visit Key West, one thing you can be sure of is that you’ll never be bored! Some of the “don’t miss” attractions for first timers include:

  • The Southernmost Point
  • Key West Butterfly Conservancy
  • Key West Custom House
  • Mel Fisher Museum
  • Key West Shipwreck Treasures Museum
  • Key West Cemetery

We recommend booking an open-air trolley ride with Old Town Trolley Tour or planning a truly amazing experience by booking a trip at This is one of the best-kept Key West secrets!

If you enjoy the water, consider planning a snorkeling trip or a sunset cruise. There’s also plenty of shopping and beautiful beaches for those who prefer to kick back and relax.

The Duval Crawl

The huge array of popular bars and restaurants is one of the best things about Key West travel! There are definitely many must-visit hotspots you won’t want to miss.

When it comes to watering holes, there are plenty of open-air, laid-back places to visit. You take a step back in time by visiting some of Hemmingway’s favorite hangouts – and create a few modern memories of your own.

Most of the well-known bars are very close to each other and you can visit them all while doing what’s known as the “Duval Crawl” (a Key West-style bar crawl). If you do it right, you’ll hit all of the following:

  • Sloppy Joe’s
  • Hog’s Breath Saloon
  • Captain Tony’s
  • Bourbon St. Pub
  • The Littlest Bar in the World
  • The Bull & Whistle

Wrap up your adventure by heading just off Duvall St. and hitting the Conch Republic Seafood Company and Schooner Wharf. Make sure you leave enough time to relax and listen to their great live music while enjoying some delicious conch fritters.

Dining in Key West

One of our favorite Key West tips is to eat as much as you can! Seriously! Key West is known for having some of the best food in Florida. Whether you want cutting-edge cuisine in an upscale restaurant or you prefer a hole-in-the-wall, you’ll find exactly what you’re looking for here.

Much of the food in Key West has both a Cuban and fresh-seafood influence. Here are a few amazing restaurants we recommend:

  • Blue Heaven –Jimmy Buffet fans love the fun atmosphere, live music, and tasty food here
  • El Meson De Pepe – a fun, lively atmosphere with great Cuban food
  • Santiago’s Bodega –
  • Latitudes – a special dining experience with unbeatable sunset views
  • Caroline’s Café – a central location that’s perfect for people-watching, the food and key lime pie are great too
  • First Flight Island Restaurant and Brewery – this cool restaurant was once the birthplace of Pan-American Airlines, now it’s home to great food, tasty beers, and amazing homemade sangria
  • Turtle Kraals – fresh oysters, ceviche, peel-and-eat shrimp, and lots of cold beer
  • Pepe’s – one of the best breakfast spots in Key West and (possibly) the best Key Lime pie
  • Cuban Coffee Queen – amazing artwork and some of the best coffee you’ll find in the Keys

These are just a few of our favorites, but as you explore the Keys, you’ll find there are many more great restaurants to please your palate.

Enjoy Your Key West Trip!

Now you know all the keys to planning an incredible Key West weekend! Need some more ideas to add to your travel bucket list? Spend some time browsing through the rest of our site!

We’ve got lots of great travel tips to help you embrace your wanderlust and explore the world!

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