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

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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...

The 48th Annual Swim Around Key West
The 48th Annual Swim Around Key West
June 21 - June 22, 2024

The 48th Annual Swim Around Key West, scheduled for Saturday, June 22, 2024, is a notable open-water swimming event. Organized by Anna Fugina, it features a challenging 12.5-mile course around Key West, with the start location at Higgs Beach. Key Highlights: The event is sensitive to tidal and weather conditions, affecting start times annually. Participants will navigate through Key West Harb...

Key Lime Festival
Key Lime Festival
July 3 - July 7, 2024

Key Lime Festival 2023: An Unforgettable Citrus Celebration The Key Lime Festival is an annual event held in the Florida Keys, celebrating the region's unique citrus, traditions, and people with a mix of eccentricity and fun. This festival is designed to provide a taste of what makes the Keys unique, from its vibrant culinary scene to its vibrant, quirky community. The upcoming 2023 Key Lime Fest...

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 & Mini-Rita Stroll
Parrots and Margaritas 5K Run/Walk & Mini-Rita Stroll
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 PR...

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Upcoming Live Entertainment

Bull & Whistle Bar
Sunday, Jun 16, 2024

  • 2:00 PM - David Warren
  • General Horseplay
    Sunday, Jun 16, 2024

  • 6:00 PM - Aaron Hudgins
  • Green Parrot Bar
    Sunday, Jun 16, 2024

  • 1:00 PM - Jess and Jill
  • 5:30 PM - Royal Hustle
  • Hank's Hair of the Dog Saloon
    Sunday, Jun 16, 2024

  • 12:00 PM - Billy Rueger
  • 5:00 PM - Jay Klein
  • 9:00 PM - Sid Duo
  • Hog's Breath Saloon
    Sunday, Jun 16, 2024

  • 12:00 PM - Elle Haley
  • 4:30 PM - Dan Harvey Duo
  • 9:00 PM - Mark King Band
  • Lagerheads Beach Bar & Watersports
    Sunday, Jun 16, 2024

  • 1:00 PM - Jonathan Williams
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    Latest News

    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...

    “Just a Few Friends Key West” Jimmy Buffett Memorial Event Set for Labor Day Weekend
    June 10, 2024

    Grab your flip-flops and margaritas, folks! The Key West City Commission has officially declared December 25th as "Favorite Son of the Conch Republic Day" to honor the legendary Jimmy Buffett. Thanks to local enthusiast Paul Menta and Mayor Teri Johnston, this tribute celebrates Buffett's lasting impact on Key West's culture and economy, from his early days at Crazy Ophelia's and Captain Tony's to...

    Hemingway 5k Sunset Run and Paddleboard Race to Make Waves in Key West
    June 06, 2024

    Get ready, athletes! This summer, the Hemingway 5k Sunset Run and Paddleboard Race is back to light up Key West with some high-energy action. Whether you're pounding the pavement or gliding on water, these two thrilling challenges are a nod to Ernest Hemingway’s adventurous spirit. Mark your calendars for Saturday, July 20, as part of the lively Hemingway Days celebration running from July 1...

    Key West Marlin Tournament: Cast for Cash and Channel Your Inner Hemingway
    June 05, 2024

    Get ready to reel in the big bucks and live out your Hemingway fantasies at the Key West Marlin Tournament, happening Wednesday through Saturday, July 17-20. With a whopping $50,000 up for grabs, anglers will be targeting blue marlin, white marlin, spearfish, and other "fun fish" species. Here’s the hook: Teams racking up the most points for marlin and spearfish over the three-day fishing f...

    Squeeze the Day: Key Lime Pie Takes Over Key West July 3-7
    May 29, 2024

    Get ready to pucker up, Key lime pie enthusiasts! The annual Key Lime Festival is back in Key West from July 3-7, celebrating Florida's beloved tangy treat. This year's lineup is packed with quirky and delicious events that are sure to zest up your summer. Pie-Eating Pandemonium The fun kicks off on July 3 at 5 p.m. with David Sloan, author of "The Key West Key Lime Pie Cookbook," at the historic...

    ‘I Love Stock Island’ Festival to Blend Cuisine, Arts and Waterfront Heritage
    May 24, 2024

    Festival Fun in the Florida Keys Get ready for a delightful blend of cuisine, arts, and waterfront heritage at the 'I Love Stock Island' Festival! This vibrant Florida Keys community, nestled near Key West, is set to showcase its charm from June 12-16. Here’s the scoop on what to expect: Wednesday Kickoff: Start the festival with an eco-friendly bang! Join the collaborative land-and-water ...

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