A well-planned Key West itinerary should include the Southernmost Point Buoy, the Ernest Hemingway Home & Museum, Mallory SquareSM, and the Key West Lighthouse. These stops offer a mix of natural beauty, literary history, and iconic views. For a deeper dive into marine life, the Key West Aquarium is worth a visit. If you’re interested in presidential history, the Harry S. Truman Little White House adds a surprising twist to your trip. These are some of the most popular Key West things to do, especially if you’re here for a Key West weekend getaway and want to make the most of your time.
A Key West weekend getaway is all about slowing down and enjoying the moment. However, it does help to have a plan that lets you experience the island without feeling rushed. This Key West itinerary includes a mix of local favorites, must-see sights, and time to explore on your own. It’s built for a weekend that feels full but never busy, giving you the space to enjoy what makes the island special.
How Can You Make the Most of Day One in Key West?
Day 1: Water Adventures and Sunset Spectacle
Start your Key West weekend getaway with the ocean at your feet and a full day of outdoor adventure. Fury Watersports offers popular morning trips that combine snorkeling and kayaking. After a short boat ride, you’ll be in the middle of the reef, swimming above coral and colorful fish. Once you dry off, the group paddles through the calm waters near a mangrove island, where it’s common to spot rays and maybe even a nurse shark in the distance. The mix of open water and quiet mangroves gives you two very different views of the local ecosystem, all in one trip.
If you’re craving speed, a guided Jet Ski tour with Fury will take you around the island at a thrilling pace. The route includes scenic views of the Southernmost Point, historic landmarks, and stretches of open ocean where you can open the throttle. It’s a great way to see the coastline while getting your heart pumping.
After your excursion, head over to Fort Zachary Taylor Historic State Park Beach. This is one of the best beaches for snorkeling in Key West, thanks to the rocky breakwaters just offshore. It’s also one of the few places where you can swim, sunbathe, and walk through a real Civil War-era fort all in the same visit. For a more relaxed option, Smathers Beach offers long stretches of soft sand and easy access to bike paths and beach rentals.
When hunger hits, the Historic Seaport is a great stop for lunch. Many of the casual waterside restaurants here serve fresh-caught grouper, mahi, and conch fritters. The open-air setting and marina views make it a laid-back spot to cool off and refuel before heading back out.
In the afternoon, explore the island with Old Town Trolley. It’s a fun and easy way to get a feel for the city while learning about the people and places that helped shape it. Hop off near Duval Street to walk among the galleries, shops, and historic bars. This stretch of Old Town always has something going on, and it’s a great place to take your time and people-watch.
A few blocks away, the Ernest Hemingway Home & Museum gives you a look inside the writer’s life. The home itself is a beautiful Spanish Colonial, and the tour includes stories from his time in Key West, his writing habits, and his love for the island. The six-toed cats, descended from Hemingway’s original pets, are part of the charm and roam freely around the property.
If you’re in the mood for something peaceful before sunset, stop by the Key West Butterfly & Nature Conservatory. It’s quiet, warm, and filled with tropical plants, waterfalls, and butterflies. There’s even a pair of flamingos that often steal the show.
As the sun starts to sink, make your way to Mallory SquareSM. The Sunset Celebration is a long-standing tradition and one of the classic Key West things to do. Street performers gather near the water’s edge, along with local artists and food vendors. It’s all set against the backdrop of one of the most famous sunsets in the world. No two nights look the same, and watching the sky shift colors over the Gulf of Mexico is a memorable way to wind down your first day.
Once the sun dips below the horizon, head just steps away to El Meson de PepeSM. This family-owned Cuban restaurant blends live music, strong mojitos, and hearty plates like ropa vieja and lechón asado. The patio often fills with the sounds of a live band, and the smell of grilled meats and plantains adds to the festive atmosphere. The night doesn’t have to end there. Just up the street, Sloppy Joe’s offers live music every night and a steady crowd of locals and visitors. This historic bar is tied to Hemingway’s time on the island, and it’s one of the most recognizable names in Old Town. If you’re up for it, check out the nearby Green Parrot Bar or head back to Duval Street for more live music, dancing, and late-night bites before wrapping up your first day in paradise.
What Should You Do on Day 2 of Your Key West Weekend Getaway?
Day Two: History, Landmarks, and Local Flavor
Your second day is a great time to explore the city’s historical layers and one-of-a-kind character. Start your morning with a walk to the Southernmost Point Buoy, one of the most photographed spots on the island. This colorful concrete marker sits just 90 miles from Cuba and has become a symbol of how far south your Key West weekend getaway can really take you.
From there, head toward the Harry S. Truman Little White House. Built in 1890 as housing for naval officers, this historic home later served as President Truman’s winter retreat. Today, guided tours bring to life the decisions he made while vacationing in Key West, offering a unique mix of presidential history and tropical scenery.
A short walk takes you to the Key West Aquarium, the oldest attraction on the island. This compact but engaging stop is especially good for families or curious travelers. The touch tanks, sea turtle feedings, and views of nurse sharks and barracudas keep things exciting without requiring much time. This stop offers a low-key mix of education and fun, especially for families or anyone curious about local marine life. It’s one of those Key West things to do that combines classic island charm with hands-on exhibits.
When you’re ready for lunch, head to Pepe’s Cafe. This local institution has been serving the island since 1909, and it still holds onto its old-school feel with creaky wood floors and hand-squeezed juice cocktails. The food is simple and hearty, featuring house specials like conch fritters, Cuban sandwiches, grilled fish, and one of the best Key lime pies on the island.
In the afternoon, you’ve got two great options: The Key West Cooking ShowSM occasionally offers pop-up experiences where you can learn to prepare Caribbean-inspired dishes in a laid-back group setting. Or stop by Bar 1, where locals and visitors alike join in for hands-on cocktail sessions or a regular happy hour if you’re looking to relax a little. Both add a personal, interactive element to your Key West itinerary.
For dinner, Blue Heaven is the kind of place people talk about long after their trip ends. The outdoor patio is filled with mismatched tables, string lights, live music, and the occasional chicken or cat roaming around. The menu mixes island favorites like jerk chicken, lobster, and fried plantains with a relaxed, come-as-you-are attitude.
If you’re still up for more, end your evening with a Ghosts & Gravestones® Tour. This theatrical and slightly spooky ride brings Key West’s haunted past to life through stories of shipwrecks, shadowy figures, and unexplained happenings. It’s a fitting final chapter to a day filled with real history, surprising stories, and local flavor.
What’s the Best Way To Wrap Up a Key West Weekend Getaway?
Key West is a small island, but it leaves a big impression. After two full days of sunshine, culture, and ocean air, you’ll head home with more than just souvenirs. A Key West weekend getaway creates the kind of memories that stay with you. Between the water sports, walking tours, historical sites, and one-of-a-kind restaurants, this island has a way of slowing time just enough to let you enjoy the moment. If you’re building a two-day Key West itinerary, the experiences here help you feel both relaxed and recharged. No matter how you spend your time, the best Key West things to do are the ones that match your own pace and personality. That’s what makes this destination such a favorite for weekend travelers. You don’t need to plan every second. Just give yourself enough space to explore, and the rest has a way of falling into place.
FAQs: What Should You Know Before Visiting Key West?
Yes, and they’re easier to find than you might think. Visiting the Southernmost Point Buoy is free and makes for a great photo opportunity. Strolling through the Historic Seaport or along Duval Street costs nothing and gives you a feel for the local culture. Many galleries and shops offer free entry, and there are often live musicians performing in public spaces. Mallory Square’s nightly Sunset Celebration is another highlight that doesn’t cost a thing. These affordable stops fit well into any Key West itinerary and are proof that some of the best Key West things to do don’t have to cost a dime. Budget-conscious travelers can still enjoy a full Key West weekend getaway without missing out on the experience.
Many of the top Key West things to do are wheelchair accessible, including Mallory SquareSM, the Key West Aquarium, and the Custom House Museum. Public sidewalks have curb cuts, and ride services like Key West Transit offer a paratransit option for visitors who qualify. Several local attractions, including the Hemingway Home and Truman Little White House, have made efforts to improve accessibility, although historic structures may have some limitations. If you’re planning a Key West itinerary with accessibility in mind, it’s a good idea to call ahead or check websites for up-to-date details. Key West continues to work toward making the Key West weekend getaway experience more inclusive for every visitor.
Key West is generally safe, especially in well-trafficked areas like Duval Street and Mallory SquareSM. Still, it’s smart to stay aware of your surroundings, especially at night. Keep belongings secure, and avoid isolated areas after dark. Sun protection is another safety must. Between midday heat and high UV levels, sunscreen, hats, and hydration are nonnegotiable. If you’re enjoying water-based Key West things to do, such as snorkeling or kayaking, always follow safety instructions from tour operators. With some basic precautions, your Key West weekend getaway will be smooth and stress-free. A well-planned Key West itinerary makes room for fun without cutting corners on safety.
