#1
Icons & Sightseeing
Mallory Square Sunset Celebration
Watch Key West’s famous nightly sunset gathering with performers, artists, boats and a waterfront crowd.
The island, ranked
100 things to do.
One Key West.
Start with the ten experiences we think define a great Key West trip, then dive into the full Top 100 by category—from fishing and water sports to history, beaches, food, music and local finds.
Editorial rankings are independent. Sponsored placements are always labeled.
This starter list balances the island’s essential landmarks, history, nature and on-the-water experiences. The full Top 100 gives you many more ways to build a trip around your interests.
Start here
The Top 10 things to do in Key West
#2
Nature & Wildlife
Dry Tortugas National Park & Fort Jefferson
Make the memorable trip about 70 miles west of Key West to Fort Jefferson, turquoise water, snorkeling and remote island scenery.
#3
History & Museums
Ernest Hemingway Home & Museum
Tour Hemingway’s Key West home, writing studio, gardens and the famous colony of polydactyl cats.
#4
Beaches & Parks
Fort Zachary Taylor Historic State Park
Combine one of Key West’s best swimming beaches with Civil War history, shady picnic areas and sunset views.
#5
Nature & Wildlife
Key West Butterfly & Nature Conservatory
Walk through a glass-domed tropical habitat filled with free-flying butterflies, colorful birds and flamingos.
#6
Tours & Cruises
Sunset Sail with Danger Charters
Sail into a Key West sunset aboard a schooner-style charter with a smaller-group, classic sailing feel.
#7
Water Sports
Florida Reef Snorkeling with Fury
Take a catamaran out to the Florida Keys reef for a guided snorkeling trip in warm tropical water.
#8
Icons & Sightseeing
Southernmost Point Buoy
Get the classic Key West photo at the colorful Southernmost Point landmark near the Atlantic end of Whitehead Street.
#9
History & Museums
Harry S. Truman Little White House
Tour Florida’s only presidential museum and learn how President Truman used Key West as a working retreat.
#10
Icons & Sightseeing
Walk Duval Street & Old Town
Explore the island’s best-known street for architecture, galleries, restaurants, bars, shopping and people-watching.
Browse by category
Find exactly your kind of Key West.
Use categories when you already know the mood: fish all day, get on the water, chase history, find the best sunset or plan a rainy afternoon.
Icons & Sightseeing
The classic landmarks, streets and sunset stops that define a first Key West visit.
5 picks →History & Museums
Writers, presidents, shipwrecks, forts and the island’s layered history.
14 picks →Water Sports
Snorkeling, parasailing, jet skis, kayaking, sandbars and active days on the water.
12 picks →Fishing
Deep sea, reef, wreck, flats and backcountry trips with Key West captains.
11 picks →Nature & Wildlife
Butterflies, dolphins, sharks, birds, gardens, reefs and protected habitat.
10 picks →Beaches & Parks
Public beaches, piers, waterfront parks and places to slow down outside.
7 picks →Tours & Cruises
Sunset sails, ferries, trolley tours, walking tours, bike tours and more.
13 picks →Food & Drink
Key lime pie, Cuban coffee, rum, breweries and destination dining.
11 picks →Nightlife & Entertainment
Live music, historic bars, pub crawls and late-night Key West energy.
6 picks →Arts & Culture
Theaters, galleries, film, photography and Key West’s creative community.
8 picks →Shopping & Local Finds
Locally made goods, markets, books and island souvenirs worth seeking out.
3 picks →A better trip list
Not just 100 names in a giant list.
Key West 100 is built to help visitors decide. Every entry has a short description, category, area and direct website link, while the searchable Top 100 lets you filter quickly on a phone.
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