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

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Upcoming Events

Fantasy Fest® 2022
Fantasy Fest® 2022
October 21 - October 30, 2022

The 2022 theme is "Cult Classics & Cartoon Chaos"  Checkout The official Fantasy Fest website for the full schedule of events.

PHiP's Annual Meeting of the Minds
PHiP's Annual Meeting of the Minds
November 03 - November 05, 2022

Parrot Heads in Paradise's annual Meeting of the Minds Convention is for members in good standing of a Parrot Heads In Paradise, Inc. chartered, official Parrot Head Club. Members of this organizatio...

Offshore Powerboat Racing World Championships
Offshore Powerboat Racing World Championships
November 06 - November 13, 2022

The Key West Offshore Racing World Championship is to begin on Sunday, November 6th, 2022 kicking off the week with a parade of the world's fastest boats. The first race starts on Wednesday the 9th w...

Key West Half Marathon & 5K
Key West Half Marathon & 5K
January 15, 2023

The 25th running of the Key West Half Marathon and 5K is on January 15th, 2023. The event expo & packet pick-up will take place outside of the Half Shell Raw Bar located at 231 Margaret Street on...

Key West Food & Wine Festival
Key West Food & Wine Festival
January 25 - January 29, 2023

14th 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 ...

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Upcoming Live Entertainment

Comedy Key West
Tuesday, Oct 4, 2022

  • 8:30 PM - The MadHouse Open Mic
  • Hog’s Breath Saloon
    Tuesday, Oct 4, 2022

  • 12:00 PM - Joel Nelson
  • 4:30 PM - Cliff Cody
  • 9:00 PM - Glass Cats
  • Sloppy Joe's Bar
    Tuesday, Oct 4, 2022

  • 12:00 PM - Brian Roberts
  • 5:30 PM - Jonathan Williams Duo
  • 10:00 PM - Turning the Tide
  • Smokin' Tuna Saloon
    Tuesday, Oct 4, 2022

  • 9:00 PM - Nick Brownell Band
  • Sunset Pier
    Tuesday, Oct 4, 2022

  • 1:00 PM - Tony Roberts
  • 6:00 PM - Robert Albury Band
  • Tipsy Rooster Liquor Store and Bar
    Tuesday, Oct 4, 2022

  • 8:00 PM - John Solinski
  • More Live Entertainment

    Latest News

    Festival to Celebrate Stock Island's Seafaring Spirit, Arts and Cuisine
    May 17, 2022

    The I Love Stock Island Festival is a family-friendly event that celebrates the island's heritage, community and unpretentious charm. The festival includes food and drink events, art strolls, live music, and other activities scheduled Wednesday throu...

    'Sailors' to Steer Quirky Craft in Key West's Minimal Regatta May 29
    May 13, 2022

    The Schooner Wharf Minimal Regatta is a wacky race where teams compete in either the kayak/canoe design or open design categories using only a sheet of plywood, two 2-by-4s, duct tape, and fasteners. Awards are given for the fastest boat, most creati...

    Key West Pride to Feature Parties, Performances and a Parade June 1-5
    May 10, 2022

    The subtropical island of Key West is to welcome revelers to its annual Pride celebrations Wednesday through Sunday, June 1-5. Scheduled festivities showcase the diversity and equality that help make the continental United States’ southernmost ...

    Swimmers to Circumnavigate Key West June 18 in 12.5-Mile Race
    May 10, 2022

    The College of the Florida Keys Swim Around Key West is a 12.5-mile open-water race in both the Atlantic Ocean and Gulf of Mexico that takes place on Saturday, June 18. Registration is open to solo competitors or relay teams of two to six swimmers, w...

    Key West Songwriters Fest Stars Top American Music Makers
    May 09, 2022

    The Key West Songwriters Festival wrapped up its 26th year with a bang, treating music lovers to over 50 shows featuring 175 chart-topping hit-makers, talented newcomers and other performing songwriters.Several thousand people gathered on Key West's ...

    Key West Songwriters Festival May 4-8
    April 02, 2022

    The Key West Songwriters Festival is a five-day event that showcases some of America’s hottest contemporary hits and classics from May 4-8. This year’s lineup includes Riley Green, Ernest, and songwriting superstars Dean Dillon, Chuck Can...

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