Our Thrilling 3-Day Key West Itinerary

Key West is an exciting destination no matter how much time you get to spend here! Planning a 3-day itinerary is perfect for a long weekend when you only have a few days to get away. Whether you plan on heading out on a President’s Day trip or looking ahead to Memorial Day or Labor Day, there are plenty of opportunities to head out for a few days of fun here in the keys.

Sometimes, going on short trips can be intimidating; you want to make your travel worthwhile and get a good feel for the place you’re visiting even if you're short on time. With our 3-day Key West itinerary, we’re confident you’ll feel like a local pro by the end of your stay. Let’s see what’s in store for you!

Day 1: Enjoy the Water

On your first day here, you have to get out on the water! That’s nonnegotiable.

All of the beaches here are beautiful, so you really can’t go wrong with your decision. Popular Key West beaches include Higgs Beach (pictured above) and Fort Zachary Taylor State Park Beach.

Whether you relax on the shore or wade into the water, you’ll have a great time! The white sand beaches are gorgeous, and the turquoise blue water is like something out of a tropical paradise. You certainly won’t be disappointed.

While you’re here, try your hand at some water sports if you’re feeling daring! Fort Zachary Taylor is an ideal spot for snorkeling, and many Key West beaches have incredible jet ski and parasailing setups, too. Add some adrenaline to the itinerary with these thrilling water sports!

After your day on the water begins to wind down, enjoy a delicious dinner at an oceanside restaurant. Bistro 245 is known for its stunning sunset views and outstanding seafood. Head over to Green Parrot Bar to end your evening feeling like a local. This iconic dive bar is a cherished local staple in the community.

Day 2: Discover Local Museums & Landmarks

There are so many museums and historical landmarks to see here. Planning a 3-day Key West itinerary is difficult because you can’t see all of them in such little time. We guess you’ll just have to plan another trip sometime!

The museums and landmarks you choose to explore depend on your personal preference. Famous residents (and part-time residents) of Key West, like Ernest Hemingway and Harry Truman, have museums commemorating their time here. Learn more about how the 33rd president spent his days off at Harry Truman’s Little White House, and see the exact room where Ernest Hemingway wrote The Old Man and the Sea at the Hemingway Home and Museum. It’s not every day you get to see the residences of such famous Americans!

If you’re interested in maritime history, the Mel Fisher Maritime Museum is highly worth visiting. Those traveling with kids should check out the Key West Shipwreck Museum. They’ll love exploring more about Key West’s history and hearing true stories of hidden pirate treasure.

While you’re in Key West, don’t miss out on your opportunity to take a photo at the Southernmost Point Buoy. This famous attraction marks the southernmost point in the continental United States, and it’s a prime photo op for first-time visitors.  

After a fun-filled educational day, head to Salute for a scrumptious meal by the ocean. Azur is another great option in the area!

Day 3: Take a Seaplane to Dry Tortugas National Park

Have you ever ridden in a seaplane? Sure, it’s an unusual mode of transportation, but seaplanes are actually quite safe and incredibly fun!

Not only do you get to see Key West from a whole new perspective in these small planes, they can also take you to exciting local sites like Dry Tortugas National Park. In fact, traveling here by seaplane is the most time-efficient transportation. The ferry takes two and a half hours, while the plane takes 45 minutes! When you only have a few days here, every minute counts.

Dry Tortugas is one of the most remote National Parks in the country and one of only a few that are entirely surrounded by water! The underwater marine life here is incredible, so if you want to go snorkeling, this is a fantastic place to do it. You should also check out Historic Fort Jefferson while you’re there.

Be aware that there are no restaurants on the island, so you’ll want to eat before you go and head back to Key West for dinner! For your final night, try our favorite Mexican restaurant, Amigos, or indulge in homemade pasta at Mangia Mangia Pasta Cafe.

Book Your Key West Getaway Directly at Dwell Key West!

We hope you are able to squeeze in as much relaxation, exhilaration, and sightseeing as you can in just a few days using our 3-day Key West itinerary. There’s enough going on here that you could spend weeks and still have more to uncover. You’ll have to come back to experience everything else our oceanside city has to offer!

When booking accommodations for your short trip, look no further than Dwell Key West. We have ideal boutique vacation rental options for any traveler!

Search our rental catalog by amenity to narrow down your search—whether you’re looking for a rental with a pool where you can relax, or a private kitchen to cook some meals in. Our newest addition, the Inn on Fleming, has already garnered glowing reviews, like this one from a recent guest who stayed in The Cornish Suite: “This was a great unit to rent for a quick trip to Key West. The location is great, the unit was nicely furnished and clean. Nice amenities with an attentive host.”

There you have it—you don’t have to take our word for it! The hundreds of reviews we receive about our units speak for themselves. We’d love to welcome you as a guest soon, too!

Whether you’re using our 3-day itinerary to book the perfect long weekend trip or just checking out ideas to squeeze into a longer trip you’re heading out on, we hope you have a blast while you’re here in Key West. And if you haven’t booked your trip yet, now is the time! Browse our available boutique vacation rentals near Duval Street now, and book your Key West vacation directly with us at Dwell!