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
1-Day Itinerary

Day 1

The Historian
2-Day Itinerary

Day 1

Day 2

More Itineraries

Upcoming Events

Sunset Celebration at Mallory Square
Sunset Celebration at Mallory Square
January 1 - December 31, 2024

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...

Hemingway Days
Hemingway Days
July 17 - July 21, 2024

Hemingway Days is a long-standing festival celebrated annually in Key West, Florida, paying tribute to the life and works of Ernest Hemingway, the eminent author who once resided there. Commencing in 1981 under the initiative of local residents, including Michael Whalton, the festival has seen substantial growth both in size and reputation, attracting globally acclaimed writers and ambitious entra...

Just A Few Friends
Just A Few Friends
August 30 - September 2, 2024

The "Just A Few Friends" event in Key West over Labor Day weekend offers a vibrant array of activities. It begins on Friday, August 30, with a proclamation by the Florida State Legislature declaring Jimmy Buffett Day and a Cheeseburger Contest welcome party on the beach. On Saturday, August 31, attendees can enjoy a bubbles brunch, walking tours, a 5K run/walk, and a Margarita bar crawl and scaven...

Parrots and Margaritas 5K Run/Walk & Flip-Flop Mile
Parrots and Margaritas 5K Run/Walk & Flip-Flop Mile
August 31, 2024 8:00 AM

WILL RUN, WALK, STROLL OR CRAWL FOR MARAGRITAS!Come Run/Walk on August 31st at 8:00 AM in Key West or participate virtually and be part of the 1st Annual Jimmy Buffett weekend celebration called Just a few Friends Key West. We will start and finish at Irish Kevin's for this awesome 5K event and rockin' post-race party because it's always 5 o'clock somewhere! NOT READY FOR A 5K? NO ...

It's 5 O'Clock in Key West: A Celebration of Jimmy Buffett
It's 5 O'Clock in Key West: A Celebration of Jimmy Buffett
September 1, 2024 6:00 AM

In 2024, Key West will host its annual Second Line Procession on September 1st, a vibrant event dedicated to celebrating the life and legacy of music icon Jimmy Buffett. This unique procession, which debuted in 2023 following Buffett's passing at 76 after a battle with skin cancer, encapsulates the essence of Key West and Buffett's spirit through music, stories, and his favorite things - rum, musi...

Fantasy Fest® 2024
Fantasy Fest® 2024
October 18 - October 27, 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...

More Events

Upcoming Live Entertainment

Boondocks Grille
Sunday, Jul 14, 2024

  • 6:00 PM - Jonathan Williams
  • Bull & Whistle Bar
    Sunday, Jul 14, 2024

  • 2:00 PM - David Warren
  • Comedy Key West
    Sunday, Jul 14, 2024

  • 8:30 PM - Greg Hahn
  • Green Parrot Bar
    Sunday, Jul 14, 2024

  • 1:00 PM - Cayman and Friends
  • 5:30 PM - The Ben Jernigan Band
  • Hog's Breath Saloon
    Sunday, Jul 14, 2024

  • 12:00 PM - Tim Hollohan
  • 4:30 PM - Royal South
  • 9:00 PM - Mark King Band
  • Irish Kevin's
    Sunday, Jul 14, 2024

  • 11:00 AM - Bradd Shadduck
  • 2:30 PM - Jeff Harris
  • 6:00 PM - Oren Polak
  • More Live Entertainment

    Latest News

    Hemingway Days Events to Salute Key West’s Literary Tradition
    June 24, 2024

    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
    June 24, 2024

    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
    June 20, 2024

    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
    June 19, 2024

    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
    June 12, 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
    June 10, 2024

    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...

    More News