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 or Croissants de France; 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

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Upcoming Events

Sunset Celebration at Mallory Square
Sunset Celebration at Mallory Square
January 01 - December 31, 2023

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 Triathlon
Key West Triathlon
December 10, 2023

Key West Triathlon Finds a New Home The renowned Key West Triathlon, a major event in the global sports calendar, will be moving to a new location for the upcoming two years. The shift is attributed to the ongoing construction at the traditional venue, the S. Roosevelt Avenue. In a display of solidarity and support for the event, the College of the Florida Keys has stepped in as the temporary ho...

New Year's Eve: Conch Shell Drop at Sloppy Joe's
New Year's Eve: Conch Shell Drop at Sloppy Joe's
December 31 - January 01, 2024

The arrival of 2024 is to be heralded on the island's Duval Street with the "drop" of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe's Bar, 201 Duval. Spectators gather on Duval for the annual gala, emceed by a rooftop host and featuring dancing in the street and a countdown to midnight recorded on a huge clock.  Inside Live music on stage noon...

The 18th Annual Florida Keys Seafood Festival: A Seafood Lover's Delight
The 18th Annual Florida Keys Seafood Festival: A Seafood Lover's Delight
January 13 - January 14, 2024

The Florida Keys Seafood Festival, a beloved tradition now in its 18th year, is more than just an event; it's a two-day celebration of the ocean's bounty. Taking place at Bayview Park in Key West, it welcomes seafood enthusiasts from all around to immerse themselves in the rich culinary culture of the Florida Keys. When is the Festival? The Festival will take place across two days: Saturday, ...

Key West Half Marathon & 5K
Key West Half Marathon & 5K
January 14, 2024

The 26th running of the Key West Half Marathon and 5K is on January 14th, 2024. The event expo & packet pick-up will take place outside of the Half Shell Raw Bar located at 231 Margaret Street on Friday and Saturday. Friday, January 12th from 3:00PM until 6:00PM. Saturday, January 13th from 12:00PM until 6:00PM. Limited packet pick-up (pre-registered participants only) available on rac...

Key West Food & Wine Festival
Key West Food & Wine Festival
January 23 - January 28, 2024

15th 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, ...

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Upcoming Live Entertainment

Boondocks Grille
Thursday, Nov 30, 2023

  • 6:00 PM - Circa 22
  • Comedy Key West
    Thursday, Nov 30, 2023

  • 8:30 PM - Mike Faverman
  • Green Parrot Bar
    Thursday, Nov 30, 2023

  • 5:30 PM - "COAST Is Clear Music & Arts Festival
  • Hank's Hair of the Dog Saloon
    Thursday, Nov 30, 2023

  • 1:00 PM - Tony Baltimore
  • 5:00 PM - Sheldon
  • 9:00 PM - Ross Brown
  • Hog's Breath Saloon
    Thursday, Nov 30, 2023

  • 12:00 PM - Ross Brown
  • 4:30 PM - Dan Harvey Duo
  • 9:00 PM - Reggie Sullivan Band
  • Irish Kevin's
    Thursday, Nov 30, 2023

  • 11:00 AM - Joe the Show
  • 2:30 PM - Oren Polak
  • 6:30 PM - Irish Kevin
  • 10:30 PM - Jeff Harris
  • More Live Entertainment

    Latest News

    Key West's Unforgettable Summer Festivities: Dirty Heads & Sublime with Rome Concert and the 26th Annual Key West Lobsterfest
    July 10, 2023

    Key West is preparing for a remarkable summer bash that promises to engage the senses and produce enduring memories. The city is gearing up to host two of the most anticipated events of the summer: the electrifying concert featuring Dirty Heads and Sublime with Rome, followed by the culinary carnival of the 26th Annual Key West Lobsterfest. Unleashing So Cal Vibes: Dirty Heads & Sublime with ...

    Over 125 'Ernests' to Compete in Key West's Annual Hemingway Look-Alike Contest
    June 16, 2023

    Key West, Florida Keys, is preparing to host its 42nd annual Hemingway Look-Alike Contest as part of the Hemingway Days festival. This year, more than 125 stout, bearded men are expected to emulate the world-renowned author's appearance and persona. Ernest Hemingway, a significant figure in American literature, had called Key West home for a significant part of the 1930s. The Competition The...

    Ernest Hemingway Days Set to Celebrate the Literary Icon from July 18-23 in Key West, Florida
    June 14, 2023

    Fans of Ernest Hemingway, the Nobel laureate, are gearing up for a week-long celebration in honor of his life, work, and lifestyle. The annual Hemingway Days festival is scheduled for Tuesday through Sunday, July 18-23, and pays homage to Hemingway's illustrious legacy. He lived and penned many of his iconic works on the island during the 1930s. The highlights of the festival will include: The...

    Key West Pride: A Colorful Commemoration of the 20th Anniversary of 1.25-Mile-Long Rainbow Flag
    June 11, 2023

    The Key West Pride Parade in Florida celebrated the 20th anniversary of the unfurling of a 1.25-mile-long rainbow flag, which had been displayed along the city's Duval Street from the Gulf of Mexico to the Atlantic Ocean during Pride 2003. Marking this significant milestone, the pride festivities incorporated a three-night light show projected by a laser array, turning the sky above Duval Street i...

    Key West Realtors Charity Fishing Tournament Slated for June 30-July 1
    May 30, 2023

    The Key West Association of Realtors has announced the upcoming Charity Fishing Tournament to be held on June 30 and July 1. This event will not only provide participants the thrill of competition, but it will also support a worthy cause, as tournament proceeds are earmarked to benefit Fair Insurance Rates in Monroe (FIRM). Tournament Details The tournament is set in the waters surrounding t...

    Key West's Quirky Regatta: Skippers Pilot Plywood-and-Duct-Tape Boats
    May 28, 2023

    The city of Key West, Florida, recently hosted the Schooner Wharf Minimal Regatta, a peculiar boat race involving over 25 vessels. While some boats capsized along the course, a majority of them managed to stay afloat, maintaining the regatta's festive atmosphere. The Offbeat Regatta's Unique Rules The uniqueness of this regatta stems from its rules. Participants are tasked with building a boat f...

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