Welcome
We hope to guide you in the right direction during your limited time in Key West. Use our itineraries as an outline and fill in the details as you explore the island! Key West is best explored on foot as much as possible. Food is such a personal thing that we will leave it off the itinerary schedules but we recommend Breakfast @ Pepe's Cafe Lunch @ Paradise Cafe or Sandy’s Cafe for a Cuban Mix sandwich and some coffee; Dinner @ Louie's Backyard, Alonzo's Oyster Bar, Blue Heaven or Seven Fish. Squeeze in some ice cream @ Flamingo Crossing. We also suggest walking by Sloppy Joe's, Rick's Bar, Capt Tony's Saloon & Hog's Breath to check out the music and let your ears guide you on your Duval Crawl. Finally catch a couple of sunsets, preferably one from Mallory Square and one at sea on a sunset cruise by The Fury or Sebago. Enjoy your vacation holiday!
First Timer
Day 1
- Ride the Conch Tour Train for an overview
- Photo at the Southernmost Point
- Visit Ernest Hemingway’s home
- Walk Duval St stopping at shops or bars of interest
- Watch the Sunset Celebration @ Mallory Square
- Walk Duval St for food & entertainment
The Historian
Day 1
- Ride the Old Town Trolley
- Consider stopping at: Ernest Hemingway’s home, Lighthouse, Audubon house, Southernmost Point, Mel Fishers Museum
- Watch the Sunset Celebration @ Mallory Square
- Walk Duval Street for food & entertainment
Day 2
- Take a Walking Tour or Rent Bicycles
- Take a sunset sail on The Fury
Upcoming Events
Sunset Celebration at Mallory Square
Key West's world-famous Sunset Celebration takes place every evening at Mallory Square close to the foot of Duval Street. Featuring both renowned local and international artists and entertainers, the event invites visitors and locals alike to enjoy the sunset at water's edge. The event begins about two hours ahead of the sunset and ends soon after the sun sets. The performance takes place 365 days...
Fantasy Fest® 2024
Fantasy Fest is an annual 10-day celebration in Key West that began in 1979 to attract visitors to the beautiful, but typically quiet season. It has grown every year, becoming the wildest extravaganza around. It's a gathering of fun-loving people from around the globe who bring their creativity and imaginations to Key West every October. The events are a whirlwind of excitement, including costumin...
Offshore Powerboat Racing World Championships
The Race World Offshore (RWO) is bringing together teams and fans for an exciting Offshore World Championship experience in Key West from November 3rd-10th, 2024. Recognized as the leading Offshore Racing Sanctioning authority in the US, RWO aims to present an unforgettable week featuring the world's top offshore race teams. The event will be held in the Race Village, situated at Truman Waterfront...
Key West Triathlon
Key West Triathlon Finds a New Home The renowned Key West Triathlon, a major event in the global sports calendar, will be moving to a new location for the upcoming two years. The shift is attributed to the ongoing construction at the traditional venue, the S. Roosevelt Avenue. In a display of solidarity and support for the event, the College of the Florida Keys has stepped in as the temporary ho...
New Year's Eve: Conch Shell Drop at Sloppy Joe's
The arrival of 2025 is to be heralded on the island's Duval Street with the "drop" of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe's Bar, 201 Duval. Spectators gather on Duval for the annual gala, emceed by a rooftop host and featuring dancing in the street and a countdown to midnight recorded on a huge clock. Inside Live music on stage noon...
Key West Half Marathon & 5K
Join Us for the Celebratory 27th Annual Key West Half Marathon & Runfest: January 18th & 19th, 2025!
Upcoming Live Entertainment
Hank's Hair of the Dog Saloon
Hog's Breath Saloon
Irish Kevin's
Schooner Wharf Bar & Grill
Sloppy Joe's Bar
Latest News
Hemingway Days Events to Salute Key West’s Literary Tradition
Get ready to channel your inner Hemingway because Key West is about to turn up the literary heat with Hemingway Days 2024. From July 16-21, the island will be buzzing with events that celebrate the legacy of one of America’s greatest writers. Here’s the lowdown: What’s Happening? Art & History Exhibit: Kick off and wrap up the fest with a unique exhibit at the Key West Mu...
Get Ready for a Lobster-Fueled Extravaganza at Key West Lobsterfest, Aug. 8-11
Craving some fresh Florida seafood? The annual Key West Lobsterfest is back, running from Thursday to Sunday, August 8-11, promising a claw-some time with a range of lobster-themed events. What's on the Menu? Thursday, Aug. 8 - Kick things off at 6 p.m. with a traditional lobster boil at Caroline’s Café, set in the historic Porter Mansion courtyard. Enjoy jumbo shrimp, corn on the c...
Hemingway Look-Alike Contest Heats Up in Key West
What's Brewing? Key West is about to get a whole lot beardier as the 43rd annual Hemingway Look-Alike Contest kicks off from July 18-21. This year's event also marks the 125th birthday of the legendary writer himself. Expect around 150 "Ernests" to flock to Sloppy Joe's Bar, vying for the title of the best Hemingway doppelgänger. Main Events Preliminary Rounds: Thursday and Friday at 6:3...
Florida Keys Fourth of July Extravaganza: Fireworks, Mermaids, and Key Lime Pie
Brace yourselves, Florida Keys! This Fourth of July is set to be a dazzling mix of beach parties, fireworks, local parades, and even mermaids. Let’s dive into the festive plans scattered across the Keys. Key West: Party Central Kickstart your morning on July 4th with the Rotary Club of Key West's annual 5k Walk/Run at 7:30 a.m. Registration opens at 6:45 a.m. at Edward B. Knight Pier. The ...
Florida Keys Fishing Tournament Highlights for Summer and Fall 2024
July 4-6: Billy Knowles Memorial Poor Boys Tarpon Fly Tournament in Islamorada. Anglers compete for the most tarpon releases over 4 feet. The event happens at Lorelei Restaurant and Cabana Bar. Visit poorboys.info or email poorboystournment@gmail.com for details. July 12-13: Key West Association of Realtors Charity Fishing Tournament in Key West. Fish for the biggest dolphin fish with prizes for ...
Will Kimbrough to Rock Key West at Memorial Fest for Jimmy Buffett
Start your Labor Day weekend off right because we’ve got some major news. Will Kimbrough, Jimmy Buffett’s long-time collaborator and co-writer of "Bubbles Up," is set to perform at the first annual “Just a Few Friends Key West” Festival. This free show will take place on September 1st at Truman Waterfront Park, right after the Second Line parade. Expect to hear from some of...