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, 2025

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...

Southernmost Regatta
Southernmost Regatta
January 20 - January 25, 2025

Experience the Excitement of The Southernmost RegattaJanuary 20–25 | Key West, FloridaVisit: southernmostregatta.com The Southernmost Regatta is a premier sailing event bringing together elite sailing teams from around the globe to compete in the stunning azure waters off Key West, Florida. Over five consecutive days of exhilarating races, vibrant sails, and unmatched sportsmanship, this regatta ...

Mile 0 Fest
Mile 0 Fest
January 21 - January 25, 2025

Experience Five Unforgettable Nights of Music in ParadiseJanuary 21st - January 25th, 2025 Mile 0 Fest Key West invites music enthusiasts to indulge in a spectacular boutique festival where the rhythms of Red Dirt and Americana music meet the serene beauty of Key West. This premier annual event combines stellar performances by iconic and emerging artists with the island’s relaxed, vibrant atmosph...

Key West Food & Wine Festival
Key West Food & Wine Festival
January 21 - January 26, 2025

16th Annual Key West Food and Wine Festival is ​a series of wine and food themed events showcasing a diverse range of wines and inventive cuisine, hosted by their passionate creators at iconic island locations. Over 20 unique events including waterfront tastings, winemaker/chef collaborations and local funky events that present an authentic taste of Key West, Florida The place to be in January, ...

Florida Keys Seafood Festival
Florida Keys Seafood Festival
February 15 - February 16, 2025

Dive into the vibrant world of the Florida Keys Seafood Festival, a two-day extravaganza held at Key West’s Truman Waterfront Park on February 15–16, 2025. This annual event, now in its 19th year, is a joyous celebration of the local fishing community, offering attendees an unforgettable experience filled with the freshest seafood, lively entertainment, and family-friendly activities. A Seafood L...

NAS Key West Airshow
NAS Key West Airshow
March 29 - March 30, 2025

Experience the Thrill of the NAS Key West Southernmost Air Spectacular! March 29-30, 2025 | Naval Air Station Key West, Boca Chica FieldPrepare for a weekend of breathtaking aerial performances, featuring military and civilian acts, at the NAS Key West Southernmost Air Spectacular. This highly anticipated event offers free general admission and showcases the U.S. Navy Blue Angels alongside a stel...

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Upcoming Live Entertainment

Boondocks Grille
Monday, Jan 20, 2025

  • 12:00 AM - John Andrews
  • Captain Tony's Saloon
    Monday, Jan 20, 2025

  • 4:30 PM - Gabriel Wright
  • Comedy Key West
    Monday, Jan 20, 2025

  • 8:30 PM - The Music Comedy Jam!
  • Hank's Hair of the Dog Saloon
    Monday, Jan 20, 2025

  • 1:00 PM - Shastina Chiles
  • 5:00 PM - Carl & Nick Norman
  • 9:00 PM - Haley Ray duo
  • Hog's Breath Saloon
    Monday, Jan 20, 2025

  • 12:00 PM - Zack Seemiller
  • 4:30 PM - Dan Harvey Duo
  • 9:00 PM - KC Johns Band
  • Irish Kevin's
    Monday, Jan 20, 2025

  • 11:00 AM - Bradd Shadduck
  • 2:30 PM - Jeff Harris
  • 6:00 PM - NY Pauly
  • 10:00 PM - Mylo O’Maolain
  • More Live Entertainment

    Latest News

    Dive into Key West’s Sunken History at the Mel Fisher Maritime Museum’s Winter Lecture Series
    January 14, 2025

    Looking for a unique reason to head to Key West this winter? The Mel Fisher Maritime Museum is hosting a fascinating lecture series that’s perfect for history buffs, treasure enthusiasts, and curious travelers alike. From Spanish galleons loaded with treasure to tales of emancipation and the maritime slave trade, this series promises to uncover the rich and complex stories that make the Fl...

    Celebrity Jeopardy! Shines the Spotlight on the Florida Keys’ Conch Republic
    January 10, 2025

    Get ready to buzz in, trivia fans! The Florida Keys’ quirky and beloved "Conch Republic" recently stole the show on the newest season of Celebrity Jeopardy!, and it's got everyone talking about this slice of paradise. The episode, which aired on January 8, marked a fabulous opportunity for the "micronation" to flaunt its charm, history, and colorful cast of characters. A Spotlight on Trivia and T...

    Key West Art and Craft Festival: A Colorful Weekend by the Waterfront
    January 10, 2025

    If you’re dreaming of an artsy getaway surrounded by sun, sea, and creativity, mark your calendars for February 22-23. The Key West Art and Craft Festival is set to transform the picturesque Truman Waterfront Park into an open-air gallery, offering visitors a delightful mix of artistic treasures, food, and tropical vibes. From 10 a.m. to 5 p.m. each day, the scenic boardwalk at the end of Southar...

    Celebrate Hemingway's Legacy at Key West's Whimsical Look-Alike Extravaganza!
    January 10, 2025

    If Ernest Hemingway were alive today, where would he be? Chances are, he'd be raising a toast at Sloppy Joe's Bar during the 44th Annual Hemingway Look-Alike Contest in Key West, Florida. From July 23-27, 2025, this charming island city transforms into a literary lover's paradise, teeming with camaraderie, humor, and Hemingway’s enduring spirit. Why This Event Should Be on Your Bucket List Wheth...

    Taste the Ocean’s Bounty: Dive into the Florida Keys Seafood Festival
    January 09, 2025

    If the idea of feasting on the freshest seafood while celebrating the hardworking fishermen who harvest it excites you, then mark your calendar for the 19th Annual Florida Keys Seafood Festival. This vibrant weekend event, held on February 15-16, offers a true taste of the ocean alongside lively music, arts, and a slice of Keys culture. Highlights of the Festival Set against the picturesque back...

    Step Back in Time: Presidential Families Weekend at Key West’s Little White House
    January 08, 2025

    Discover History, Heritage, and Charm This Presidents Day This Presidents Day weekend, journey to Key West, Florida, for an unforgettable experience that merges history, heritage, and tropical charm. From February 13 to 17, the iconic Harry S. Truman Little White House will host Presidential Families Weekend, a captivating series of events celebrating America’s storied past and the preservation o...

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