🦜 Tipsy’s Must-See Attractions of Key West
Key West is much more than beaches, bars and sunsets. This little island has presidents, pirates, writers, shipwrecks, treasure hunters, six-toed cats and enough strange history to keep Tipsy wandering around with a map for days.
Here are the places we think every visitor should experience at least once.
1. Ernest Hemingway Home & Museum ✍️🐈
Old Town • History • Literature • Famous Cats
Walk through the home and gardens where Ernest Hemingway lived and wrote during his Key West years. The property is also home to its famous colony of polydactyl, or six-toed, cats, some descended from Hemingway's original cat.
🦜 Tipsy Says: Come for Hemingway. Stay because a six-toed cat has decided you aren't allowed to leave.
Visit the Hemingway Home & Museum
2. Southernmost Point 🌴📸
South & Whitehead Streets • Landmark • Photo Stop
You've seen the picture. Now go get your own. The colorful Southernmost Point buoy has been a Key West landmark since 1983 and has become one of the island's classic photo stops.
🦜 Tipsy Says: Go early in the morning unless standing in line under the Florida sun is part of your vacation plan.
3. Harry S. Truman Little White House 🇺🇸
Truman Annex • Presidential History • Guided Tours
President Harry Truman spent considerable time working and relaxing here during his presidency. Today it's Florida's only presidential museum and offers guided tours through the historic home.
🦜 Tipsy Says: Apparently presidents figured out the Key West thing long before the rest of us.
Visit the Truman Little White House
4. Key West Lighthouse & Keeper's Quarters 🔦
Old Town • History • Views • 88 Steps
Built after the previous lighthouse was destroyed in the hurricane of 1846, the present lighthouse dates to 1848. Climb its 88 steps for panoramic views across Old Town, then explore the Keeper's Quarters below.
🦜 Tipsy Says: Eighty-eight steps sounds suspiciously like exercise, but the view makes a convincing argument.
Visit the Key West Lighthouse
5. Mallory Square Sunset Celebration 🌅
Waterfront • Sunset • Street Performers • Key West Tradition
Before the sun disappears into the Gulf, Mallory Square turns into a nightly Key West street festival with performers, artists, vendors and crowds gathering along the waterfront.
🦜 Tipsy Says: At least once during your stay, watch Key West stop what it's doing and applaud the sun.
6. Mel Fisher Maritime Museum ⚓💰
Old Town • Shipwrecks • Treasure • Maritime History
Key West's treasure-hunting history gets very real here. The museum focuses on maritime archaeology, historic shipwrecks and artifacts recovered from the waters surrounding the Florida Keys.
🦜 Tipsy Says: Actual sunken treasure. Suddenly that metal detector you bought seems perfectly reasonable.
Visit the Mel Fisher Maritime Museum
7. Key West Shipwreck Treasure Museum ⚓
Mallory Square • Shipwrecks • Wreckers • Observation Tower
Long before tourism became Key West's business, shipwrecks were big business. This museum recreates a 19th-century wrecker's warehouse and tells the story of the salvagers who helped make early Key West remarkably prosperous. You can also climb its 65-foot observation tower for views over the harbor.
🦜 Tipsy Says: Key West history contains considerably more treasure and questionable behavior than your high-school history class.
Visit the Key West Shipwreck Treasure Museum
8. Key West Butterfly & Nature Conservatory 🦋🌺
Upper Duval • Butterflies • Tropical Gardens • Nature
Step into a climate-controlled tropical habitat filled with butterflies, exotic birds, flowering plants and waterfalls. It's peaceful, beautiful and also a pretty clever escape from the midday Key West heat.
🦜 Tipsy Says: Finally, an attraction where the birds are almost as colorful as I am.
Visit the Butterfly & Nature Conservatory
9. Audubon House & Tropical Gardens 🌺🏡
Old Town • Historic Home • Gardens • Art
Built in the 1840s for Captain John Huling Geiger, a wealthy harbor pilot and master wrecker, this beautifully restored home offers a glimpse into prosperous 19th-century Key West. Its rescue from demolition in 1958 helped spark the island's historic preservation movement.
🦜 Tipsy Says: Old Key West before frozen drinks came with tiny umbrellas.
Visit Audubon House & Tropical Gardens
10. The Oldest House Museum & Garden 🏡
Duval Street • Architecture • History • Old Key West
Built in 1829, the Oldest House offers a look at early Key West architecture and domestic life right in the middle of modern Duval Street.
🦜 Tipsy Says: Walk in from modern Duval Street and suddenly you've traveled about two centuries.
11. Fort Zachary Taylor Historic State Park 🏰🌊
Truman Annex • Civil War History • Beach • Snorkeling
This one does double duty. Explore the historic pre-Civil War fort, then change into your swimsuit and spend the rest of the day at one of Key West's favorite beaches.
🦜 Tipsy Says: History lesson in the morning. Snorkeling in the afternoon. That's a field trip I can support.
Visit Fort Zachary Taylor Historic State Park
12. Key West Museum of Art & History at the Custom House 🎨
Mallory Square • Art • History • Architecture
The striking red-brick Custom House beside Mallory Square is worth seeing before you even walk through the door. Inside, exhibits explore Key West and Florida Keys art, people and history.
🦜 Tipsy Says: A good place to figure out why this tiny island became so wonderfully strange.
Visit the Custom House Museum
13. Fort East Martello Museum 👻🏰
Atlantic Side • Civil War Fort • Art • Legends
A Civil War-era brick fort that's now part history museum, part art museum and part keeper of some of Key West's stranger legends. Its exhibits cover local history, folk art and the island's paranormal lore.
🦜 Tipsy Says: Old fort. Ghost stories. Weird Key West history. I'm listening.
Visit Fort East Martello Museum
14. Duval Street 🌴🍹
Old Town • Shopping • Restaurants • Nightlife • People-Watching
You don't really visit Duval Street. Eventually, Duval Street just happens to you.
It runs through the heart of Old Town and connects restaurants, galleries, shops, historic buildings, bars and some of the finest people-watching available anywhere in the Florida Keys.
🦜 Tipsy Says: Walk it during the day. Walk it again at night. You will swear it's a completely different street.
15. Wander Old Town & the Back Streets 🚲🌺
Old Town • Historic Homes • Architecture • Hidden Gems
Some of the best Key West sightseeing doesn't require a ticket. Leave Duval behind for an hour and wander through the historic residential streets. You'll find Bahamian-style homes, tropical gardens, tiny lanes, chickens, bicycles and pieces of old Key West hiding everywhere. Old Town remains the island's dense, highly walkable historic core.
And since The Tipsy Parrot is already tucked into this part of Key West, the adventure starts when you step outside.
🦜 Tipsy Says: Put the phone away. Pick a street you've never walked down. Getting a little lost is part of the plan.
🚂 Bonus: Ride the Conch Tour Train
Old Town • Sightseeing • History • First-Day Adventure
This is touristy, and that's exactly why I'd include it.
A narrated ride around Key West is a great way for first-time visitors to get oriented, hear the island's stories and figure out which places they want to return to later. Current tour packages combine the Conch Tour Train with other historic attractions, including the Truman Little White House and Shipwreck Museum.
🦜 Tipsy Says: Ride it early in your trip. Consider it reconnaissance with better scenery.
⛵ The Big Adventure: Dry Tortugas National Park
About 70 Miles West of Key West • Fort Jefferson • Snorkeling • Bucket List
This is the one attraction I'd deliberately separate from everything above because it isn't really a quick Key West sightseeing stop.
Dry Tortugas National Park lies roughly 70 miles west of Key West and centers on massive Fort Jefferson, surrounded by brilliant water, coral, marine life and remote islands. Access is by boat or seaplane.
🦜 Tipsy Says: If you have the time and budget, this is one of those stories you'll still be telling years from now.
Plan a Dry Tortugas Visit with the National Park Service
🦜 Tipsy's Key West Advice
Don't try to turn Key West into a checklist.
See Hemingway's house. Climb the lighthouse. Take the ridiculous Southernmost Point photo. Learn about the treasure hunters and wreckers. Watch the sunset at Mallory Square.
But then leave some room in the schedule to wander.
Take a street you've never walked before. Follow some music. Stop because a building looks interesting. Talk to somebody at the bar. Pet a six-toed cat if it permits you.
The famous attractions tell you the history of Key West. The spaces between them are where you start to understand the place. 🌴🦜