If you’re ever looking for the “sweet spot” when it comes to vacation time, a long weekend is usually perfect. A day trip may often feel too short and a week-long vacation may stretch your relaxation abilities just a bit, but a three-day weekend is just right.

That’s why we’re going to talk about how to spend the perfect long weekend in Key West. With three days ahead of you, what should you plan first? As Key West locals, we know the top spots! We’ve put together the best itinerary for a three-day getaway in Key West.

Traveling to Key West

You might be thinking that you’re going to have to spend a whole day traveling down to Key West and a whole day to get back. While that may have been the case a few years ago, there are tons of flight options for you to get down to Key West.

Many major US cities, like Houston, Chicago, Miami, Ft. Lauderdale, and Boston, are offering direct flights so you don’t have to spend your time making endless connections just to enjoy the sunny skies.

Day One - Enjoy the Water

Key West is filled with plenty of outdoor activities that are fun and safe. Whether you’re the adventurous type or looking for a calmer day, there’s plenty to do. As Key West locals, we know the ins and outs of a great Key West weekend. Keep reading to learn more about how to enjoy your long weekend getaway.

If you’re looking for calmer waters, head out on one of the charters in the area. Not only will you get a brief tour around Key West, but many offer snorkeling and a chance to see local wildlife - like parrot fish, nurse sharks, turtles, coral reefs, and much more. These creatures have flourished over the last year, so it’s an amazing opportunity to spot an abundance of Key West critters.

For those looking for a bit more physical work, try a sea kayak or paddleboarding. You can either take them out at your leisure or go with a guide to explore certain sites.

If you’re not all watered out (impossible really) then take a boat to one of Key West’s top restaurants: Latitudes. It’s ideal for date night as you’ll get a front-row seat to the sunset and beautiful views before taking the boat back to shore.

Day Two - Explore Nature

One of the must-see places during your three-day stay is Dry Tortugas National Park. Here, you’ll be able to visit Fort Jefferson, which played a surprisingly important role in the aftermath of the Civil War. 

Dry Tortugas National Park is a bit off the beaten path and it’ll take you a little over two hours to make the trip. With an early start to the day, make sure you go to one of the best breakfast places in town, Glazed. This small bakery has some of the best donuts we’ve ever had!

If you’re not too tired, spend the evening taking a stroll down Duval Street. Cheeky Key Westers have dubbed it “the longest street in the world” because it runs from the Gulf of Mexico all the way to the Atlantic Ocean.

Duval has plenty of shops, sites, and restaurants to check out. Take a look at our top seven faves in the area to be pointed in the right direction. 

Day Three - Learn a Bit About History

Did you know that one of America’s most famous writers, Ernest Hemingway, had a residence in Key West? Furthermore, did you know that it’s home to some unique cats?

You can go visit his old residence, still in the Hemingway family, and the rare multi-toed cats that live there. The cats eat well, are free to lounge on Hemingway’s furniture (because it is also their house), and even have their own cemetery near the garden, where kitties Frank Sinatra, Zsa Zsa Gabor, Marilyn Monroe, and Mr. Bette Davis are buried. These cats have become so famous that they have even gone to court… Read the NY Times article here.

You’ll also have to go visit the southernmost point in the United States. This marker is just 90 miles away from Cuba! Talking about southernmost… you can also visit the Southernmost House Hotel - one of the oldest Key West houses (converted into a hotel) and dine at the magnificent Seaside Cafe at The Mansion.

Last, we recommend you head to the Key West Historic Memorial Garden. With 36 bronze busts of some of the most influential people in Key West’s history, it’s a perfect mix of nature and history you can’t pass up. 

For your final evening, we recommend heading to Mallory Square. Catch some street performers and watch the beautiful Key West sunset with a drink in hand.

Ready for Your Weekend Getaway?

We’re ready to welcome you to Key West. If you need help with reservations or finding out what to do, reach out and get your free travel plan. We can’t wait to see you!