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

Day 2

More Itineraries

Upcoming Events

Key Lime Festival
Key Lime Festival
June 30 - July 04, 2023

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...

Hemingway Days
Hemingway Days
July 20 - July 22, 2023

Hemingway Days is a long-standing festival celebrated annually in Key West, Florida, paying tribute to the life and works of Ernest Hemingway, the eminent author who once resided there. Commencing in 1981 under the initiative of local residents, including Michael Whalton, the festival has seen substantial growth both in size and reputation, attracting globally acclaimed writers and ambitious entra...

Fantasy Fest® 2023
Fantasy Fest® 2023
October 20 - October 29, 2023

Every October, Fantasy Fest brings thousands of fun-loving people from around the world to Key West for an incredible 10-day extravaganza. Since its inception in 1979, the event has grown to become the wildest party around, featuring costuming, parades, libations and excitement. It is an opportunity to let your creativity and imagination run wild and to experience paradise in a unique way. The 20...

Offshore Powerboat Racing World Championships
Offshore Powerboat Racing World Championships
November 05 - November 12, 2023

The Key West Offshore Racing World Championship is to begin on Sunday, November 5th, 2023 kicking off the week with a parade of the world's fastest boats. The first race starts on Wednesday the 8th with 1st race time at 10 am, followed by 12:30 pm, 1:30 pm, and 2:30 pm start times. The second race starts on Friday the 10th and the third race starts on Sunday the 12th, both with the same race sta...

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, ...

More Events

Upcoming Live Entertainment

Captain Tony's Saloon
Monday, May 29, 2023

  • 4:30 PM - Gabriel Wright
  • Hank's Hair of the Dog Saloon
    Monday, May 29, 2023

  • 12:30 PM - Shastina Chiles
  • 4:30 PM - TBD
  • 8:30 PM - TBD
  • Hog's Breath Saloon
    Monday, May 29, 2023

  • 12:00 PM - Zack Seemiller
  • 4:30 PM - Nick Brownell
  • 9:00 PM - Dan Harvey Band
  • Irish Kevin's
    Monday, May 29, 2023

  • 11:00 AM - Jeff Harris
  • 2:30 PM - Bradd Shadduck
  • 6:00 PM - NY Pauly
  • 10:00 PM - Jack Wolf
  • Kiki's Sandbar Bar & Grille
    Monday, May 29, 2023

  • 6:00 PM - Andy Westcott
  • La Te Da
    Monday, May 29, 2023

  • 8:30 PM - 3Sum - Piano Bar
  • More Live Entertainment

    Latest News

    Dolphin Fish Tournament in Florida Keys Set for June 23-25
    May 16, 2023

    Anglers from all walks of life will be gathering in the Florida Keys for a highly anticipated event - the Florida Keys PBA Dolphin Tournament, taking place from June 23-25. This tournament is not just a test of skill, but also a noble initiative to benefit two praiseworthy causes, the Autism Society of the Keys and the Love Fund. About the Event The Florida Keys PBA Dolphin Tournament is hos...

    Celebrating Two Decades of the Sea-to-Sea Rainbow Flag at Key West Pride 2023
    May 08, 2023

    Overview The globally recognized Key West Pride event is scheduled to take place from Wednesday through Sunday, June 7-11, 2023. This year, the festival marks the 20th "birthday" of Key West's iconic 1.25-mile sea-to-sea rainbow flag. The Key West Business Guild will present a three-night laser light show to celebrate this landmark occasion and to honor the Florida Keys' unifying "One Human Famil...

    Key West's VFW Fishing Tournament Set for June 16-18
    May 03, 2023

    Key West's 11th annual VFW Fishing Tournament is inviting all fishing enthusiasts to compete over a three-day period, from June 16-18. Male and female anglers of all ages, including first responders, veterans, and active-duty service members, have a chance to test their skills against five species of fish. Tournament Details Target Species: The tournament aims to catch five specific species ...

    Swimmers and 'Mermaids' to Circle Key West During 12.5-Mile Race June 17
    May 02, 2023

    On June 17, swimmers, relay teams, and "mermaids" will embark on a unique aquatic adventure as they circle Key West in a 12.5-mile open-water race through the Gulf of Mexico and Atlantic Ocean. The College of the Florida Keys' Swim Around Key West welcomes competitors of all ages, as they vie for awards in various age categories. Sanctioned by the World Open Water Swimming Association, the event c...

    Kinetic Sculpture Parade of Recycled Creations to Mark Earth Day in Key West
    March 21, 2023

    The Papio Kinetic Sculpture and Art Bike Parade will take place in Key West on April 22 to celebrate Earth Day. The parade will feature colorful mobile sculptures made from recycled materials, powered only by human effort. The event is in honor of Stanley Papio, a folk artist who used to weld recycled car parts, pipes, and wire to create sculptures. The parade is intended to inspire eco-friendly r...

    Key West Woman Scores Historic Win at March Merkin Permit Tournament
    March 21, 2023

    Kathryn "Kat" Vallilee of Key West has made history at the March Merkin Permit Tournament, becoming the first woman to win the tournament since its inception in 2006. The Florida Keys event, which targets permit, a notoriously elusive gamefish, saw 25 teams of elite permit enthusiasts take part in the 2023 tournament under challenging fishing conditions. Tournament veteran Vallilee was named grand...

    More News