Key West Travel Guide: Things to Do, Best Time to Visit & Itinerary
Experience the quirky charm, literary history, and turquoise waters of America's southernmost city, where Caribbean vibes meet historic intrigue. From the sunset celebrations at Mallory Square to the coral reefs of the Dry Tortugas, Key West offers an unforgettable escape at the end of the road.
Key West is more than just a destination; it’s a state of mind. Floating at the very end of the Florida Keys archipelago, this tiny island packs a massive punch of character, history, and Caribbean flair. It is a place where roosters have the right of way, the sunsets are applauded nightly, and the influence of Bahamian wreckers and Cuban cigar makers is felt on every corner. Whether you are seeking the solitude of a hidden garden or the revelry of Duval Street, Key West welcomes you with an open mind and a cold drink.
Separated from the mainland by 42 bridges and over 100 miles of ocean, the island feels distinct from the rest of the United States. It’s a tropical sanctuary that has inspired legends like Ernest Hemingway and Tennessee Williams. Here, the pace slows down to “island time,” urging you to trade your wristwatch for the rhythm of the tides and the daily celebration of the setting sun.
Seasonal Weather Guide
Plan your perfect getaway with our detailed seasonal forecast.
The Conch Republic State of Mind
To understand Key West, you must understand the Conch Republic. In 1982, in a tongue-in-cheek protest against a U.S. Border Patrol blockade, the city mayor declared Key West an independent nation, declared war on the U.S., surrendered one minute later, and applied for foreign aid. This spirit of irreverent humor and fierce independence defines the local culture. You aren’t just visiting a city; you are visiting a community that prides itself on being “One Human Family,” welcoming eccentrics, artists, and dreamers from all walks of life.
Walking the streets of Old Town, you will see this history reflected in the architecture. Gingerbread-trimmed Victorian mansions sit next to humble shotgun cottages, shaded by massive banyan trees and royal poincianas. It is a living museum where the stories of shipwrecks, pirates, and naval history are woven into the very pavement you cycle on.
Things to Do
Unforgettable experiences await you.
Day Trip to Dry Tortugas National Park
Take a ferry or seaplane 70 miles west to explore a massive 19th-century coastal fortress surrounded by pristine coral reefs.
Sunset Celebration at Mallory Square
Join the daily carnival of street performers, musicians, and food vendors as hundreds gather to watch the sun dip into the Gulf of Mexico.
The Hemingway Home and Museum Tour
Walk through the rooms where Ernest Hemingway wrote his classics and meet the descendants of his famous six-toed cats.
Duval Street Pub Crawl
Experience the legendary nightlife by hopping between historic saloons, open-air bars, and cabaret shows along the island's main artery.
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The Icons You’ll Want to See
The Ernest Hemingway Home and Museum - Explore the Spanish Colonial estate where the author lived for nearly a decade. Admission is $18 USD, and it is located in the heart of Old Town, just 0.5 mi from Duval Street. Don’t forget to look for the six-toed cats.
Fort Zachary Taylor Historic State Park - Located at the southern tip of the island (1.5 mi from the center), this park offers the best swimming beach in Key West and a Civil War-era fort. Entry is $6 USD per vehicle or $2.50 USD for pedestrians/bikers.
The Southernmost Point Buoy - The famous photo op marking the lowest latitude in the continental U.S. It is free to visit, but lines can be long. Located at the corner of South and Whitehead Streets, 1 mi from Mallory Square.
Truman Little White House - Florida’s only presidential museum, which served as the winter White House for Harry S. Truman. Guided tours are approximately $24 USD. It sits inside the lush Truman Annex, 0.3 mi from the waterfront.
Essential Guide
Everything you need to know.
Must-Visit Spots
Local Cuisine
Where to Stay
Travel Tips
Insider Tips
Planning Your Visit
Getting to Key West is part of the adventure. You can fly directly into Key West International Airport (EYW), but many travelers prefer flying into Miami (MIA) and driving the stunning Overseas Highway. The 3.5-hour drive crosses 42 bridges, including the famous Seven Mile Bridge, offering breathtaking ocean views on both sides of the road.
Once you arrive, leave the car parked. Parking is expensive and scarce in Old Town. The best way to get around is by bicycle or the free Duval Loop bus. The island is only 2 miles by 4 miles, making it incredibly bike-friendly. Bring plenty of reef-safe sunscreen, a hat, and comfortable walking shoes, as you will spend most of your time outdoors soaking up the tropical atmosphere.
When to Visit
Choose the perfect time for your adventure.
Peak Season: Winter & Spring (December - April)
Pros
- Perfect weather with low humidity
- bustling atmosphere and nightlife
- full calendar of festivals
Cons
- Highest hotel rates of the year
- heavy crowds at major attractions
- restaurant reservations required well in advance
Shoulder Season: Late Spring (May - June)
Pros
- Warm but manageable heat
- excellent fishing conditions
- slightly lower accommodation prices
Cons
- Humidity begins to rise
- afternoon showers become more frequent
- mosquito activity increases
Off-Peak: Late Summer & Fall (August - October)
Pros
- Lowest prices on hotels and flights
- no lines at popular museums
- warmest ocean temperatures for water sports
Cons
- Risk of hurricanes and tropical storms
- oppressive humidity
- some local businesses close for vacation
Key West is a destination that stays with you long after the tan fades. Whether you come for the world-famous Key Lime pie, the literary history, or simply to watch the sun melt into the Gulf of Mexico, you will leave understanding why so many people drive to the end of the road and decide to never turn back.
Sample Itineraries
Classic Key West Weekend
A relaxed itinerary hitting the literary landmarks, best beaches, and famous nightlife of Old Town.
Day 1: History & Sunsets in Old Town
- Morning: Start with a rooster-filled breakfast at Blue Heaven for around $40 USD, then walk two blocks to the Hemingway Home and Museum ($18 USD per person) to see the study where he wrote To Have and Have Not.
- Afternoon: Climb the 88 steps of the Key West Lighthouse across the street for panoramic views, then rent a bike ($15 USD) to cruise down Duval Street and grab a cuban mix sandwich at Sandy’s Cafe.
- Evening: Head to Mallory Square around 6:00 PM to secure a spot for the sunset celebration, watching cat acrobats and swallowing swords before enjoying a seafood dinner at Conch Republic Seafood Company for $80 USD.
Day 2: Sun, Sand, and Civil War History
- Morning: Pack a cooler and cycle to Fort Zachary Taylor Historic State Park ($6 USD entry), where you can tour the pre-Civil War fortress and snorkel off the rocky breakwater.
- Afternoon: After drying off, head back to town for a late lunch at DJ’s Clam Shack ($25 USD), then visit the Mel Fisher Maritime Museum ($17 USD) to see real gold and emeralds recovered from the shipwrecked Atocha.
- Evening: Experience the spooky side of the island on a Ghosts & Gravestones trolley tour for $35 USD per person, followed by a nightcap at the historic Green Parrot Bar to listen to live local jazz.
Day 3: The Southernmost Experience
- Morning: Wake up early to beat the line at the Southernmost Point Buoy for a photo at 8:00 AM, then walk to the Key West Butterfly and Nature Conservatory ($15 USD) to walk among hundreds of winged creatures.
- Afternoon: Enjoy a casual lunch at The Lobster Shack, then take a 90-minute jet ski tour around the entire island (approx. $150 USD) to see the naval air station and sandbars from the water.
- Evening: Conclude your trip with a sunset sail on a schooner like the Danger Charters Wind & Wine cruise ($110 USD per person), featuring premium wines and hors d’oeuvres while sailing the harbor.
The Adventurer's Escape
An action-packed guide focusing on the Dry Tortugas, kayaking through mangroves, and backcountry fishing.
Day 1: Arrival & Island Orientation
- Morning: Arrive at Key West International Airport (EYW) and pick up your rental Jeep, then head straight to Garbo’s Grill for their famous fish tacos ($15 USD) served from an Airstream trailer.
- Afternoon: Check into your hotel and immediately head to the Key West Bight to rent paddleboards ($25 USD/hour) to navigate the calm waters around the marina and spot nurse sharks.
- Evening: Walk the Historic Seaport boardwalk and grab a table at the Half Shell Raw Bar for a dozen oysters and a pitcher of beer ($45 USD total) while watching the fishing charters unload their catch.
Day 2: The Dry Tortugas Expedition
- Morning: Board the Yankee Freedom III ferry at 7:00 AM ($200 USD per person) for the 2.5-hour journey to Dry Tortugas National Park, enjoying the included breakfast on board.
- Afternoon: Spend the day snorkeling the vibrant moat wall of Fort Jefferson, exploring the massive brick fortifications, and birdwatching on Bush Key before the ferry departs at 2:45 PM.
- Evening: Return to Key West exhausted but happy around 5:30 PM, then relax with a casual dinner at El Siboney on Catherine Street for authentic Paella Valenciana ($50 USD for two).
Day 3: Mangroves & Backcountry
- Morning: Drive to the Geiger Key Marina for a guided kayak eco-tour ($60 USD per person) through the winding mangrove tunnels, looking for iguanas, rays, and tropical jellyfish.
- Afternoon: Drive back toward Stock Island to have lunch at the Hogfish Bar & Grill ($40 USD), a local favorite with open-air seating and arguably the best hogfish sandwich in the Keys.
- Evening: Charter a small boat for a backcountry fishing trip ($400-$600 USD) to catch tarpon or bonefish as the sun sets over the flats, a truly serene experience away from the Duval Street noise.
Day 4: Flora & Farewell
- Morning: Visit the Key West Tropical Forest & Botanical Garden ($10 USD) on Stock Island to walk the boardwalks through native hammocks and wetlands that most tourists never see.
- Afternoon: Return to Old Town for a slice of chocolate-dipped Key Lime Pie at Kermit’s ($6 USD) and pick up final souvenirs at the Kino Sandals factory where leather sandals are made by hand.
- Evening: Enjoy a farewell dinner at Latitudes on Sunset Key (requires a ferry reservation, approx. $150 USD dinner), offering the most upscale dining view of the Key West harbor.
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