Landlubber's Guide to Key West: Sun, Fun, and Quirky Adventures
We see you, drylanders! If you're looking for things to do in Key West without setting sail, you're in for a treat. This tropical paradise offers a treasure trove of land activities that'll keep you entertained from sunrise to sunset. It’s fun to find the hidden, indoor gems of our well-known island paradise.
Here’s your anti-seafaring and sand-avoidant guide to the southernmost point of the continental United States. Keep this handy in case of inclement weather, for rainy moments, or when you want to beat the heat. Stay planted on terra firma, explore indoor activities, and still enjoy your vacation to the max!
1. All Aboard! Discover Key West by Trolley or Train
Want to see all of the island without breaking a sweat? Hop on the Conch Tour Train or the Old Town Trolley for a whimsical ride through the island's history and hotspots.
Both tours pass by the Little White House in Old Town – where Presidents Roosevelt, Truman, Eisenhower, Kennedy, Carter, and Clinton have stayed over time.
These guided tours are equal parts informative and entertaining, with conductors who know how to spin a yarn. Families with kids, elderly travelers, and anyone seeking to avoid sunburns, seasickness, or weather will enjoy these air-conditioned tours. They’re comfortable ways to explore the island.
Learn about the island's fascinating past, from its early settlers to its role in the Civil War. Discover hidden gems you might have missed on foot, and get insider tips on the best local haunts. Plus, you can hop on and off at various stops, making it easy to explore Key West attractions at your own pace.
2. Take an Indoor Cultural Museum Tour
Begin your cultural adventures at the Key West Butterfly and Nature Conservatory, where you can surround yourself with hundreds of fluttering beauties in a tropical paradise. This indoor attraction stands as a spectacular option for the summer afternoon sun shower or when you simply need a break from the sun. The enclosed Conservatory is wheelchair and stroller accessible.
Next, head to the Mel Fisher Maritime Museum to learn about shipwrecks and treasure hunting – it's the closest you'll get to a pirate's life without leaving dry land. If someone in your group fears getting seasick, rest assured that this museum offers a great way to enjoy maritime history while keeping your feet firmly planted on the ground.
At the Key West Shipwreck Museum, you can go on an indoor treasure hunt for artifacts, try interactive exhibits, and watch films about the area’s most infamous shipwrecks. Then, if you’re up for the challenge, you can climb to the top of the lookout tower for outdoor panoramic views of the island, without setting sail.
3. Write Your Own Key West Story: Explore the Legacy of Famous Novelists, Playwrights, Poets
Key West enjoys a strong literary tradition, with a long list of writers producing great works from the Florida Keys. In recent years, Judy Blume co-founded a bookstore here, aptly called Books & Books. This cozy, air-conditioned bookstore provides a super spot to beat the heat while finding your next vacation read.
The playwright of "A Streetcar Named Desire," Tennessee Williams, called the island home. So be sure to visit the Tennessee Williams Museum. Explore his life and works, and maybe even catch a live performance of one of his plays.
The poet Robert Frost spent 16 winters writing here. While his former home is no longer open to the public, you might catch a glimpse of the cottage and enjoy other sites on Caroline Street where he “wintered.”
And of course, there’s the Ernest Hemingway Home and Museum where you can wander through rooms where Papa penned some of his greatest works. Lush gardens surrounding the home offer plenty of shady spots to relax and enjoy the beauty of the property.
Take some notes and add your name to the long list of well-regarded writers that have found inspiration here, including Ann Beattie, Elizabeth Bishop, Meg Cabot, Philip Caputo, Billy Collins, John Hersey, Alison Lurie, Thomas McGuane, James Merrill, Shel Silverstein, Wallace Stevens, Robert Stone, Robert Richardson, and Richard Wilbur. Who knows? You might find inspiration for your own great American novel!
4. Feast Your Way Through Key West's Best Places to Eat
Key West may be surrounded by water, but our sea-avoidant friends can still enjoy a gastronomic journey through the island's culinary scene. Many restaurants offer air-conditioned indoor seating to enjoy a meal in comfort.
For breakfast, head to Blue Heaven for their famous Benedicts. The laid-back atmosphere and free-roaming chickens add a dash of whimsy to your meal.
Be sure to grab a slice of heavenly key lime pie from Kermit's Key West Key Lime Shoppe – it's a local delicacy you can't miss!
And don't forget to sample some conch fritters – a Key West staple! Try our Tin Cup Chalice Bar & Chill to enjoy the famous fritters with a wedge salad at Margaritaville Beach House Key West. Available on our lunch menu, 12–5 pm.
Wash it all down with a refreshing rum runner, bloody mary, or whistle-wetter of choice (Hey, when in Margaritaville…).
Your taste buds will thank you for this flavorful expedition through the island!
5. Shop 'Til You Drop: Unique Finds on Duval Street
No dry land guide to the area would be complete without mentioning Duval Street. This mile-long stretch is the beating heart of Key West's shopping and nightlife scene. Browse our unique boutiques selling everything from tropical-themed knick-knacks to high-end art. Plus, many shops and restaurants along Duval Street offer accessible options for those with mobility concerns.
Pick up a souvenir t-shirt with a cheeky slogan, or treat yourself to some locally made jewelry. Don't miss the Kino Sandal Factory, where you can watch artisans craft handmade leather sandals – fabulous footwear for your on-island adventures!
As night falls, Duval Street transforms into a party haven. Bar hop your way down the street, enjoying live music and colorful characters along the way.
6. See the Sunsets by Land: Don't Miss Key West's Most Colorful Show Key West: More To Do on Land than You’d Think!
The nightly Sunset Celebration at Mallory Square’s a must-see attraction. Street performers, artists, and food vendors gather to create a carnival-like atmosphere at twilight. Watch in awe as jugglers, acrobats, and even trained house cats perform death-defying feats. Grab a coconut from a local vendor, peruse the artisan crafts, and join in the applause as the sun dips below the horizon.
However, if you’d prefer a less active venue for your twilight views, try Fort Zachary Taylor Historic State Park or Higgs Beach. They are both accessible by land. Fort Taylor’s historical stonework (completed in the 1800s) offers a historical setting to watch the sun lower through the fort's arches. Higgs Beach provides an even quieter and more relaxed atmosphere on the southern shore.
Key West: More To Do on Land than You’d Think!
From literary haunts to culinary delights, from cultural gems to over-the-top street performances, Key West offers a smorgasbord of land activities for every type of traveler. This tiny island packs a big punch when it comes to entertainment, relaxation, and pure, unadulterated fun!
Whether you're a culture vulture, a foodie, or just looking to soak up some sun and good vibes, we’ve got you covered. Don't let the lack of sea legs hold you back – dive into the unique charm of this tropical paradise and create memories that'll last a lifetime.
Ready to plan your Key West adventure? Start by booking your accommodations in Margaritaville now – this popular destination fills up fast!
Be sure to check out our special offer for summer 2025: Summerzcool! Stay longer and enjoy a dining credit, too!
