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...

Conch Republic Independence Celebration 2024
Conch Republic Independence Celebration 2024
April 19 - April 28, 2024

The Conch Republic Independence Celebration 2024 marks its 42nd anniversary with a variety of events showcasing their unique heritage and vibrant culture. Celebrations begin on Friday, April 19th, with an opening ceremony at Mallory Square, including the raising of colors and a Conch Shell-Horn Salute, accompanied by live entertainment. This is followed by a kick-off party and a Conch Shell Blowin...

Key West Songwriters Festival
Key West Songwriters Festival
May 1 - May 5, 2024

The Key West Songwriters Festival, now in its 27th year, stands as the largest event of its kind globally, renowned for propelling the careers of prominent country music artists like Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser, and Maren Morris. This festival has earned a reputation as a career catalyst for emerging talents in the country music scene. Drawing music ...

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...

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Upcoming Live Entertainment

Boondocks Grille
Friday, Apr 19, 2024

  • 6:00 PM - Andy Wescott Band
  • Celtic Conch Public House
    Friday, Apr 19, 2024

  • 5:00 PM - Tom Curtis
  • Comedy Key West
    Friday, Apr 19, 2024

  • 5:30 PM - Hemingway In a Funny Way
  • 8:30 PM - Mike Cronin
  • Green Parrot Bar
    Friday, Apr 19, 2024

  • 5:30 PM - Damon Fowler
  • Hank's Hair of the Dog Saloon
    Friday, Apr 19, 2024

  • 1:00 PM - Victoria
  • 5:00 PM - Adam Lufkin
  • 9:00 PM - Mark King Duo
  • Hog's Breath Saloon
    Friday, Apr 19, 2024

  • 12:00 PM - Elle Haley
  • 12:00 PM - Justin Angelo
  • 4:30 PM - Mark King Band
  • 4:30 PM - Mark King Duo
  • 9:00 PM - Nick Netherton Band
  • More Live Entertainment

    Latest News

    Team High Stakes Wins Inaugural Key West Sailfish Tournament
    April 16, 2024

    The inaugural Key West Sailfish Tournament ended with Team High Stakes taking the top spot, earning a cool $56,370. Captained by Jason Jonas, a Key West local, and featuring a mix of talent including his father Don Jonas, they landed four sailfish, securing their victory. Notably, Team Reel Wheels, skippered by Captain Clayton Baker, trailed closely, with Reece Kramer from Pompano Beach snagging t...

    Unwind and Unplug in the Florida Keys’ Backcountry
    April 15, 2024

    Ready to leave the fast lane for a bit? The Florida Keys backcountry offers just the ticket—a serene escape into nature's arms, away from the humdrum of everyday life. Picture this: endless skies, quiet waters, and a rich tapestry of marine life, all waiting in a secluded part of the world mostly unknown to tourists. Located on the north side of the iconic Overseas Highway, this shallow par...

    Toe Shoes and Tutus with a Twist: Les Ballets Trockadero Dances into Key West
    April 12, 2024

      Grab your tickets, folks! Les Ballets Trockadero de Monte Carlo, famously known as "the Trocks," are set to pirouette onto Key West this April 25th. What's the big deal? Picture this: a burly troupe of male dancers decked out in flamboyant tutus and toe shoes, performing pitch-perfect parodies of ballet classics like "Swan Lake." Yes, it’s all the ballet pre...

    Key West Sings: A Symphony of Songwriters
    April 10, 2024

    Good morning, Key Westers! While you've been tuning into your regular playlists, the music world is gearing up for something a bit more live, a tad more lyrical, and absolutely unforgettable. Mark your calendars for May 1-5, because Key West is transforming into the ultimate melody mecca with the 28th annual Key West Songwriters Festival. What's the Buzz? Imagine this: more than 225 of the cr&eg...

    Sharks, Strategies, and Surprises: The Spanish Fly Shark Tournament Recap
    April 10, 2024

    Good afternoon, ocean aficionados and sports enthusiasts! This weekend, the waters off the Florida Keys were more than just crystal clear—they were the arena for the ultimate test of skill, strategy, and a touch of luck in the renowned Spanish Fly Shark Tournament. The big catch of the day (or rather, the big releases) went to the Calico Creek team, hailing from Massachusetts and the sunny ...

    Unwind in Paradise: Your Ultimate Escape to the Florida Keys
    April 10, 2024

    The quintessential escape plan for when the real world gets a bit too real – a rejuvenating getaway to the Florida Keys. Let's face it, folks, our daily grind, coupled with the non-stop pings from our devices, can leave us feeling like a squirrel on a never-ending treadmill. It's precisely in these moments that the soul craves a reset button, and boy, do we have a suggestion for you! Enter...

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