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
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...

Sofia Talvik's "Center of the Universe" Tour
Sofia Talvik's "Center of the Universe" Tour
April 10, 2024 6:00 PM

Embark on a FREE Journey Through Sound and Story with Sofia Talvik's "Center of the Universe" Tour Experience the enchanting melodies of Sofia Talvik as she brings her latest masterpiece, "Center of the Universe," to the heart of the Florida Keys. This 2024 tour is a celebration of Sofia's ninth studio album, a project that has captivated audiences and critics alike, solidifying her position as a...

7 Mile Bridge Run
7 Mile Bridge Run
April 13, 2024 6:00 AM

The Annual 7 Mile Bridge Run will take place on April 13th, 2024. Registration is only available online at 7mbrun.com The race's 1,500 runners will traverse the entire segmental bridge spanning 6.79 miles over open water and connecting Marathon with Ohio Key in the middle of the Florida Keys. In 1982, Marathon Runners Club began a new tradition to mark the official opening of the 7 Mile Bridge. ...

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...

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Upcoming Live Entertainment

Boondocks Grille
Friday, Mar 29, 2024

  • 6:00 PM - Howard Livingston
  • 6:30 PM - Alfonse
  • Comedy Key West
    Friday, Mar 29, 2024

  • 8:30 PM - Emma Willman
  • Green Parrot Bar
    Friday, Mar 29, 2024

  • 5:30 PM - Colin Davis And Night People
  • Hank's Hair of the Dog Saloon
    Friday, Mar 29, 2024

  • 1:00 PM - Sharesse
  • 5:00 PM - Myles Mancuso
  • 9:00 PM - Chris Toler
  • Heroes Bar & Liberty Lounge
    Friday, Mar 29, 2024

  • 8:00 PM - Ike Kanakanui
  • Hog's Breath Saloon
    Friday, Mar 29, 2024

  • 12:00 PM - Elle Haley
  • 4:30 PM - Jason Lamson & Andy Westcott
  • 9:00 PM - Mike Stone Band
  • More Live Entertainment

    Latest News

    Ahoy, Mateys! The Conch Republic Turns 42, and Key West Is Throwing a Bash Fit for a Pirate
    March 18, 2024

    In the realm of quirky celebrations, Key West, Florida, is hoisting the colors for the Conch Republic's 42nd birthday with a bash that's as unconventional as its origin. From April 19 to 28, the island chain is set to come alive with over 20 colorful events that promise to blend a pirate's sense of adventure with a dash of island whimsy. This is not your average birthday party. A Little Rebellion...

    Sofia Talvik's "Center of the Universe" Tour Hits the Florida Keys
    March 18, 2024

    Ready to embark on a musical journey that’s truly out of this world? Sofia Talvik, the siren of Swedish-American folk, is docking her “Center of the Universe” tour at the Key West Library this April. If you’ve ever wondered what it sounds like when the melancholy of the Swedish soul meets the heart of American folk, this is your chance to find out. Who’s Sofia? A tr...

    A Dallas Angler Clinches Victory at the Prestigious March Merkin Permit Tournament
    March 18, 2024

    In an exhilarating turn of events deep in the Florida Keys, Robert Dougherty of Dallas, Texas, clinched victory at the 2024 March Merkin Permit Tournament, an event that wrapped up on March 14. Dougherty’s masterful catch-and-release of two permit fish, both reeled in on the nail-biting final day of the competition, scored a combined length of 130 centimeters. This impressive feat, measured ...

    Marine Conservation to Highlight Mote’s Ocean Fest in Key West April 20
    March 12, 2024

    Just when you thought Key West couldn't get any more ocean-centric, the Mote Marine Laboratory is gearing up to make a splash with its 2024 Ocean Fest. Scheduled for April 20, smack-dab in the middle of the Florida Keys’ protected marine sanctuary, this shindig is more than just a nod to the big blue—it's a call to arms for ocean lovers and conservationists alike. And hey, it's free, s...

    Mixing Art and History: Key West's Truman Little White House Brews Up TRU-ly Amazing Events
    March 11, 2024

    Just when you thought Key West couldn't get any more picturesque, the Harry S. Truman Little White House throws in a splash of paint and a dash of history to create something truly unique. In a blend that only the island can pull off, two TRU-ly Amazing Art events are set to offer creative spirits a once-in-a-lifetime experience — painting alongside a descendant of Truman himself. First up,...

    Blowin' in the Wind: Key West's Annual Conch Shell Blowing Contest
    March 10, 2024

    It's not every day that you see folks trying to make music with a conch shell, but down in Key West, Florida, that's exactly the spectacle dozens gathered to witness at the annual Conch Shell Blowing Contest this weekend. The competition ended on a high note with a tie in the men's division between Peter Drake and Brian Cardis, proving that "pucker power" is no joke when it comes to playing tunes ...

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