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

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The Historian
2-Day Itinerary

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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...

Key West Pride
Key West Pride
June 5 - June 9, 2024

Key West's PRIDE 2024 festival celebrates diversity with a tropical island vibe and a packed schedule of events. The event honors the philosophy of 'One Human Family' and highlights the island's open and accepting atmosphere. The festival's program is filled with unique events starting from Tuesday, June 6, with a pre-opening Pride event, "Real Men Do Drag" charity, to Sunday, June 11 with the Pri...

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...

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...

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Upcoming Live Entertainment

Bull & Whistle Bar
Thursday, May 23, 2024

  • 2:00 PM - David Warren
  • Comedy Key West
    Thursday, May 23, 2024

  • 8:30 PM - Tony V
  • General Horseplay
    Thursday, May 23, 2024

  • 6:00 PM - Sharese
  • Green Parrot Bar
    Thursday, May 23, 2024

  • 5:30 PM - Doc Elliot & Friends
  • Hank's Hair of the Dog Saloon
    Thursday, May 23, 2024

  • 1:00 PM - Reggae Lou
  • 5:00 PM - Carl & Nick Norman
  • 9:00 PM - Homegrown
  • Hog's Breath Saloon
    Thursday, May 23, 2024

  • 12:00 PM - Adam Lufkin
  • 4:30 PM - Dan Harvey Duo
  • 9:00 PM - Tony Baltimore Band
  • More Live Entertainment

    Latest News

    Hemingway Days Heat Up with Key West Marlin Tournament
    May 21, 2024

    By the Numbers: Event Dates: July 17-20, 2024 Location: Stock Island Marina Village, Key West, FL Cash Prizes: $50,000 up for grabs Register: Limited to 75 boats at KeyWestMarlin.com The Scoop: Buckle up, anglers! The Key West Marlin Tournament is making waves again, riding the crest of the Annual Hemingway Days Celebration. From July 17-20, Stock Island Marina Village will be buzzing wi...

    Catch the Big One: Key West Gator Club Dolphin Derby
    May 21, 2024

    Fishing Fanatics, Rejoice! The Key West Gator Club Dolphin Derby is back after a hiatus, and it’s making waves from June 21-23. Anglers, this is your shot at $15,000 in guaranteed cash prizes, perfectly timed with the peak dolphin fishing season in the Florida Keys. Headquarters: The action happens at Beachside Resort & Residences, 3841 N. Roosevelt Blvd. What's at Stake: Grand Priz...

    ‘Local’s Choice’ Tips from Laura Zequeira-Smith
    May 15, 2024

    Local flavor spices up Key West's cozy getaway spot at Alexander’s Guesthouse, where Laura Zequeira-Smith, the shining star and general manager, champions a "home away from home" vibe for the LGBTQ community and its allies. Formerly of the big leagues—specifically the Mandarin Oriental in New York—Laura accepted an offer from friends and current owners, Raul Diaz and Orlando Torr...

    Reel in the Fun: Key West's VFW Fishing Tournament Casts a Big Net with $65K Prize Pool
    May 13, 2024

    The weekend of June 14-16, Key West is not just a sun-soaked paradise but also the battleground for the 12th annual VFW Fishing Tournament, where over $65,000 in prizes is up for grabs. Anglers from all walks of life, including military members, veterans, first responders, and even kids, will compete in various categories, hoping to land the biggest catch. The star attraction? A whopping $50,000 c...

    Key West Pride to Celebrate Diversity and Disco June 5-9
    May 08, 2024

    Retro vibes and rainbow flags are set to make a splash at Key West Pride 2024, scheduled for June 5-9. Channel your inner disco diva and dive into a celebration of diversity with a 1970s disco-era theme, brought to you by the Key West Business Guild. This sun-soaked fest promises a lineup that's as colorful as the island's coral reefs—from late-night dance-offs to sunset sails, not forgettin...

    Solo Swimmers and Teams to Race 12.5 Miles Around Key West in June 8 Challenge
    May 07, 2024

    Ready to take on an exhilarating swimming challenge? Mark your calendars for June 8, when the annual College of the Florida Keys Swim Around Key West kicks off! This isn’t your typical dip in the pool—participants will brave a 12.5-mile open-water race that circles the entire island, testing their endurance against both the Atlantic Ocean and Gulf of Mexico. Starting bright and early ...

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