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

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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...

Tennessee Williams Birthday Party
Tennessee Williams Birthday Party
March 26, 2024 5:00 PM

The Tennessee Williams Museum celebrates the 113th birthday of renowned playwright Tennessee Williams with an array of events in March 2024. The main attraction, a birthday party at the museum on March 26 from 5:00 PM to 7:00 PM, is open to all and features champagne, cake, and the announcement of winners in both the short story and poetry contests. These contests, integral to the celebration, inv...

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
Thursday, Feb 22, 2024

  • 6:00 PM - Snacks & Five
  • Comedy Key West
    Thursday, Feb 22, 2024

  • 8:30 PM - Kevin Bozeman
  • General Horseplay
    Thursday, Feb 22, 2024

  • 6:00 PM - Sharese
  • 9:00 PM - Cayo Hueso Riot
  • Green Parrot Bar
    Thursday, Feb 22, 2024

  • 5:30 PM - Tony Baltimore & The Wilde Awake
  • Hank's Hair of the Dog Saloon
    Thursday, Feb 22, 2024

  • 1:00 PM - Tony Baltimore
  • 5:00 PM - Alex Anthony
  • 9:00 PM - Chris Toler
  • Hog's Breath Saloon
    Thursday, Feb 22, 2024

  • 12:00 PM - Dan Harvey
  • 4:30 PM - Jason Lamson Duo
  • 9:00 PM - Nick Netherton Band
  • More Live Entertainment

    Latest News

    Feast Your Eyes (and Taste Buds) on This: Taste of Key West 2024
    February 20, 2024

    Just when you thought Key West couldn't get any more appetizing, the 29th annual Taste of Key West rolls into town on March 25, ready to tantalize your taste buds and maybe even get you a little tipsy (responsibly, of course). Kicking off at 6 p.m. sharp at the scenic Truman Waterfront Park—yep, that's the one with the killer views of Key West Harbor—the night promises a smorgasbord of...

    Conch Shell Blowing Contest: Key West's Quirkiest Musical Tradition Takes Center Stage
    February 08, 2024

    In the bustling heart of Key West, where the sun shines just a bit brighter and the ocean breeze carries tales of the old and new, there’s a sound that’s distinctly the island’s own. This isn’t your run-of-the-mill music fest; it’s the 61st annual Conch Shell Blowing Contest, hitting the garden of the Oldest House Museum (322 Duval St.) Saturday, March 9. Think you've...

    Time Travelers and Tethered Balloons: Unraveling the UFO Mystery Over Fort Jefferson
    February 08, 2024

    In the latest episode of "Things You Didn't Know You Needed to Know," Scott C. Waring of ufosightingsdaily.com has kicked up a storm with his report on a supposed UFO fleet hovering over Fort Jefferson in sunny Key West, Florida. Dated February 1, 2024, and spotted on none other than Google Earth, this revelation could have you rethinking your next beach vacation. Now, before you start picturing ...

    Key West Toasts to Tennessee Williams: A Month-Long Literary Celebration
    February 06, 2024

    It's time to tip your hats to a literary legend in Key West, folks! This March, the island that Tennessee Williams once called home is rolling out the red carpet to celebrate the life and works of the iconic playwright. Williams, who crafted classics like “Night of the Iguana” and “The Rose Tattoo” from his Key West residence, is the star of the show all month long—co...

    Riding the Musical Wave in the Florida Keys: A Symphony of Sounds from Shore to Shore
    February 01, 2024

    It's not just the sea breeze that's making waves across the Florida Keys these days—there's a musical revolution afoot, and it's hitting every note from Grammy-winning ballads to classical symphonies. Whether you're a jazz enthusiast, a classic rock devotee, or a country music fan, the Keys are turning up the volume with a lineup that's as diverse as the islands themselves. Let's start wi...

    GardenFest: The Ultimate Nature Lover’s Day Out in Key West
    January 26, 2024

    Set your calendars for March 2nd, folks! The Key West Tropical Forest & Botanical Garden is throwing open its gates for "GardenFest Key West - The Green Market Place". And guess what? It's free! From 10 a.m. to 4 p.m., at 5210 College Road, you can immerse yourself in a unique open-air "living museum". This place isn’t just any garden - it's the only frost-free subtropical moist forest ...

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