Key West is the best walking town in Florida. A compact Old Town packed with conch houses, rooftop bars, history and roosters strutting down the sidewalk, and almost everything worth doing is within walking distance. Here are the best things to do in Key West, from a local who keeps coming back.
Most surprising: the Key West Butterfly & Nature Conservatory
Best history stop: the Truman Little White House
Favorite hangout: Dante’s pool bar and restaurant
Spookiest walk: past the Key West Cemetery at night
Getting around: walk, then ride the Old Town Trolley for the far-out stops
1. Walk Old Town and Duval Street
I love walking the streets of Key West. It’s the best way to see everything: the conch houses, the hidden courtyards, the bars and galleries, and the chickens that rule the sidewalks. Start on Duval Street and wander the side streets of Old Town.
2. Ride the Conch Train or Old Town Trolley
For a quick overview of the island’s history, hop on a narrated tour. I spent four days in Key West and the Conch Train tour was one of the best ways to get my bearings. The Old Town Trolley is hop-on, hop-off, so you can use it to get around too.
3. Key West Butterfly & Nature Conservatory
Hundreds of butterflies flutter freely through a glass-domed tropical garden on Duval Street, and you’ll spot flamingos too.
4. Harry S. Truman Little White House
President Truman spent 175 days of his presidency at this winter White House, and the guided tour walks you through the rooms where he worked and relaxed.
5. Ernest Hemingway Home & Museum
Hemingway lived and wrote at 907 Whitehead Street in the 1930s, and today the house is one of the most visited attractions in Key West. The real stars are the dozens of resident cats, many of them six-toed descendants of Hemingway’s cats. It’s on my list for my next trip down this month, and I’ll update this with my take.
6. Walk Past the Key West Cemetery at Night
Key West is one of the most haunted towns in Florida, and the historic cemetery is a big part of why. Many of the tombs sit above ground, stacked like little white houses.
Want the stories that go with it? Book the Key West Ghost & Mysteries Guided Tour, and see Robert the Doll and more in my guide to haunted places in Florida.
7. Do the Duval Crawl
If you like to partake in a few adult beverages, the Duval Crawl is a Key West rite of passage: bar-hopping your way down Duval Street, with live music spilling out of nearly every door. Pace yourself and stay hydrated, because it’s hot.
8. Chill at Dante’s Pool Bar
9. Play Pickleball by the Beach
Higgs Beach Park has public courts right by the water.
10. Catch the Sunset at Mallory Square
Every evening, Mallory Square turns into a street party for sunset, with buskers, food carts and a crowd that cheers when the sun hits the water. Get there about an hour early.
11. Snap a Photo at the Southernmost Point
The striped buoy at Whitehead and South Streets marks the southernmost point in the continental U.S., about 90 miles from Cuba. Go early in the morning to beat the photo line.
12. Snorkel the Reef
The only living coral barrier reef in the continental U.S. sits just offshore. A snorkel trip is the easiest way to see it.
👉 Planning to get in the water? See our picks for the best Key West snorkeling tours, including Dry Tortugas day trips.
Prefer a sunset vibe? Try the Dip & Sip Afternoon Snorkel, or look for sharks, rays and dolphins on the Shark & Wildlife Viewing Adventure.
Compare snorkel trips: Fury reef snorkel (morning or afternoon) · Sebago snorkel sail with live music
13. Day Trip to Dry Tortugas National Park
About 70 miles west of Key West, Dry Tortugas is home to massive Fort Jefferson and some of the clearest water in Florida. It’s a full-day trip by boat or seaplane, so book well ahead.
Ferry details: Yankee Freedom ferry to Dry Tortugas: prices, schedule and what’s included
14. Rent a Golf Cart
Walking covers Old Town, but a golf cart makes it easy to reach the beaches and the far end of the island. Read my Key West golf cart rental guide, or book one with Golf Cart Rental Casa Marina.
Where to Stay in Key West
Stay in or near Old Town so you can walk everywhere:
- Southernmost Inn: near the Southernmost Point and the quieter end of Duval
- Lighthouse Hotel: steps from the Hemingway House and the lighthouse
- Authors of Key West Guesthouse: historic guesthouse in Old Town
- Beachside Resort & Residences (formerly Key West Marriott Beachside): resort pool and beach outside of Old Town
On a budget? See where to stay in the Florida Keys on a budget. Bringing a car? Read do you need a car in Key West first.
Plan the Rest of Your Trip
Driving down? My Florida Keys road trip guide covers the stops along the way, and the Key West itinerary planner helps you map out your days. Going in late October? Don’t miss my Fantasy Fest guide.
Key West FAQ
What are the best things to do in Key West?
Top picks include walking Old Town and Duval Street, the Key West Butterfly and Nature Conservatory, the Harry S. Truman Little White House, the Ernest Hemingway Home and Museum, sunset at Mallory Square, snorkeling the reef and a day trip to Dry Tortugas National Park.
Is Key West walkable?
Yes. Old Town Key West is compact and very walkable, and walking is the best way to see it. Bikes, golf carts and the trolley cover anything farther out.
What is special about the Hemingway House in Key West?
The Ernest Hemingway Home and Museum at 907 Whitehead Street is where Hemingway lived and wrote in the 1930s. It’s also famous for its dozens of resident cats, many of them six-toed (polydactyl).
Is the Key West Cemetery worth seeing?
Yes, especially if you like history or a little spooky atmosphere. Many of the tombs are above ground, which makes it eerie after dark. For the full haunted experience, book a guided ghost tour.
How many days do you need in Key West?
Three to four days lets you walk Old Town, hit the main attractions, get out on the water and still catch a couple of Mallory Square sunsets. Add a day if you want to do Dry Tortugas.
When is the best time to visit Key West?
Winter and spring bring the most pleasant weather and the biggest crowds. Late October is Fantasy Fest, Key West’s wildest festival, so book early if you’re going then.
🗺️ This spot is on our interactive Florida map
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- An interactive map on your phone — tap any pin for our honest local take.
- Ready-made itineraries — timed to beat the gates.
- New spots every week — buy once, updates for life.
It’s the guide we wish existed every time someone asked us “okay, but where would YOU go?”
