Key West was one of our stops on a Virgin Voyages cruise, and while we managed to fit in a lot during our day there, it became pretty clear this is a destination that deserves way more than just a few hours. Between the colorful streets, iconic landmarks, rooftop views, and nonstop energy, Key West has a way of making you want to slow down and stay awhile. It seemed to be a mix of New Orleans and West Palm Beach in one – a little bit of high energy and fun, along with some relaxation and laid-back atmosphere.
Here’s everything we did during our stop, plus ideas for where to stay, tours worth booking, and the best time to visit if you’re planning a longer trip. Be prepared to say hello to a lot of chickens and roosters!
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Things to Do in Key West
Here are the top things to do in Key West even if you have only one day.
Southernmost Point Buoy
One of the most iconic stops in Key West is the Southernmost Point Buoy, marking the southernmost point of the continental United States. It’s a popular spot, but well worth the stop — especially if you can get there earlier in the day. The line will get pretty long midday, but still worth the wait to get that photo!
Mallory Square
Mallory Square sits at the heart of Key West’s waterfront culture and comes alive each evening as the island winds down for the day. As the sun drops toward the horizon, the area fills with live music, street performers, local artists, and food carts, creating an easygoing, community-driven scene rather than a polished tourist production. It’s a place to linger, grab a drink, wander the pier, and take in one of the most talked-about sunsets in the Florida Keys—whether you’re visiting for the first time or returning for another round.
Sloppy Joe’s: A Key West Classic
A visit to Sloppy Joe’s is practically a Key West rite of passage. With live music, a lively crowd, and deep roots in the island’s history, it perfectly captures the fun, laid-back spirit Key West is known for.
Wandering Duval Street
Duval Street is the heart of Key West, and wandering it without a plan is half the fun. We explored unique local shops, picked up souvenirs, and the five of us who cruised together even got permanent bracelets — a fun and meaningful reminder of the trip.
One standout stop was Doc’s on Duval, a newer spot on Duval with excellent drinks and snacks and an easygoing vibe. I loved that it had a porch area overlooking Duval street so we didn’t miss a beat.
Rooftop Drinks at The Mansion
For great views and a more relaxed atmosphere, we stopped at the Sky Bar at The Mansion. From up there, you can see the bright blue ocean that makes the Florida Keys so special. The Keys are located near the third-largest barrier reef in the world, and on the day we visited, it was very windy, which made the waves fast and choppy. It was still a cool experience to see the ocean like that at the southernmost point of the continental U.S.
Key West Butterfly & Nature Conservatory
The Key West Butterfly and Nature Conservatory offered a peaceful break from the busier parts of the island. Walking through a tropical environment surrounded by hundreds of butterflies was unexpectedly calming. You see other tropical creatures aside from butterflies, too!
Harry S. Truman Little White House
We also visited the Harry S. Truman Little White House, which served as President Truman’s winter White House during his time in office. He spent nearly 175 days there, using the home as a place to work, meet with advisors, and step away from Washington. Several other U.S. presidents, including Bill Clinton, have also stayed there over the years. Today, it’s preserved as a museum and offers an interesting look at both presidential history and Key West’s strategic importance, adding depth to a destination often known for its beaches and nightlife.
Key Lime Pie Is a Must
No trip to Key West is complete without trying key lime pie. Whether you prefer it classic, frozen, or dipped in chocolate, it’s the island’s signature dessert and the perfect way to cool down. I actually didn’t think I would like it, but I was pleasantly surprised when we tried it! It was delicious. We got ours at Key West Lime Pie Co. located on Greene St.
Best Time to Visit Key West
Late Spring (March–May): This is often considered one of the best times to visit. The weather is warm without being overwhelming, humidity is more manageable, and the island has a lively energy without feeling completely overrun. It’s a great time to walk around, enjoy rooftop bars, and explore without constantly escaping the heat (though occasional hot spring days can still happen).
Winter (December–February): These months bring picture-perfect weather and a festive atmosphere, which makes them extremely popular. Expect ideal temperatures — and higher prices and heavier crowds, especially around holidays. If you don’t mind busy streets and packed bars, it’s a beautiful time to be in Key West. We were there in January and it was a little crowded, but very manageable. We were never held up.
Summer and Early Fall (June–November): This is when travel requires more flexibility. Hurricane season runs from June through November, with the highest risk typically between August and October. Along with extreme heat and high humidity, storms can disrupt travel plans, including cruise itineraries and flights. While crowds thin out and prices drop, visitors during this time should be prepared for weather-related changes.
Late Fall (November): Late fall can feel like a reset. Hurricane risk begins to taper off, temperatures become more comfortable, and the island starts to feel lively again without winter-level crowds, making it a popular shoulder-season choice.
If Key West is a cruise stop, it’s possible to enjoy it year-round. But for a longer stay, late spring or late fall offers the best balance of weather, crowd levels, and overall experience.an make it work year-round. But if you’re planning a longer stay? Late spring or late fall is where it’s at.
Where to Stay in Key West
If you’ve got more than a day (and honestly, you should), here are some solid options:
- Key West Villas – The top reviewed place to stay on Booking.com with a score of 9.7. This is a great location right in the downtown area.
- H2O Suites – An adults only resort close to downtown and the beach. This is another top reviewed hotel on Booking.om with a score of 9.4.
- Casa Marina Key West, Curio Collection by Hilton – If you know me, you know I love a Curio Collection by Hilton hotel. This is a beachfront hotel that is about a half a mile from downtown. They are highly rated for their sustainability efforts, too.
- The Perry Hotel & Marina Key West – A highly rated property that is about a 5-minute drive from downtown on Stock Island Marina.
- Oceans Edge Resort & Marina – The Southernmost Point is 5 miles from here, but many proclaim the location is perfect with panoramic water views. It’s also about 2 miles from the airport.
- You can view more options and ratings here.
Tours Worth Booking
Got extra time? These tours are actually worth it:
- Shark and Wildlife Viewing Catamaran Tour *highly rated
- Dolphin Watching and Snorkeling Eco Cruise Tour
- Old Town Trolley 13-Stop Hop-On Hop-Off Tour
- Key West Conch Train Tour
- Glass Bottom Boat Reef Tour with Sunset Option
- Ghosts & Gravestones Guided Trolley Tour
Top Museums in Key West
- Ernest Hemingway Home and Museum
- Harry S. Truman Little White House (mentioned above)
- Key West Museum of Art & History at the Custom House
- Mel Fisher Maritime Museum
- Key West Shipwreck Museum
- Key West Lighthouse & Keeper’s Quarters Museum
- Fort East Martello Museum
- Oldest House Museum & Gardens
- USCGC Ingham Maritime Museum
- Florida Keys Eco-Discovery Center
Why Key West Is Worth Coming Back To
Even with just one day, Key West made an impression. The historic sites, the rooftop bars, the quirky shops, the tropical scenery—it all just works. You can absolutely hit the highlights in a cruise stop, but this is the kind of place that really rewards slowing down and taking your time. We’re already thinking about when we can get back.
