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

Jimmy Buffett and The Coral Reefer Band
Jimmy Buffett and The Coral Reefer Band
February 11, 2023

Jimmy Buffett and The Coral Reefer Band are bringing their Second Wind Tour to Key West, Florida, with two performances scheduled for Thursday and Saturday, February 9th and 11th at the Coffee Butler ...

Tennessee Williams Birthday Party
Tennessee Williams Birthday Party
March 26, 2023

On March 26th, the Tennessee Williams Museum will be hosting a birthday celebration for Tennessee Williams, who would have been 112. The event will include champagne, cake, and the announcement of the...

7 Mile Bridge Run
7 Mile Bridge Run
April 01, 2023

The Annual 7 Mile Bridge Run will take place on April 1st, 2023. Registration is only available online at 7mbrun.com The race's 1,500 runners will traverse the entire segmental bridge spanning 6.79 m...

NAS Key West Airshow
NAS Key West Airshow
April 15 - April 16, 2023

Naval Air Station Key West is inviting the public to join them in celebrating two centuries of Navy history in Key West and Monroe County during the Southernmost Air Spectacular. This two-day event on...

Conch Republic Independence Celebration 2023
Conch Republic Independence Celebration 2023
April 21 - April 30, 2023

The Conch Republic is celebrating its 41th birthday this year with a 10-day festival of fun and games. The Conch Republic is a symbolic nation that was established in 1982 when the Florida Keys secede...

Key West Songwriters Festival
Key West Songwriters Festival
May 03 - May 07, 2023

The Key West Songwriters Festival is an annual event held in Key West, Florida that celebrates the faces, voices and stories behind the songs. Most of the festival shows are free to enter, and some re...

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Upcoming Live Entertainment

Boondocks Grille
Sunday, Feb 5, 2023

  • 6:00 PM - Fried Newt
  • Green Parrot Bar
    Sunday, Feb 5, 2023

  • 1:00 PM - Barry Cuda & The Sharks
  • 3:00 PM - Richard Crooks Annual Second Line
  • 5:30 PM - Bill Blue Memorial
  • Hank's Hair of the Dog Saloon
    Sunday, Feb 5, 2023

  • 1:00 PM - Kari Wolf
  • 5:00 PM - Sheldon Benton& K-Rush
  • 9:00 PM - Myles Mancuso
  • Hog's Breath Saloon
    Sunday, Feb 5, 2023

  • 12:00 PM - Tim Hollohan
  • 4:30 PM - Alex Anthony
  • 9:00 PM - Mike Veal Band
  • Irish Kevin's
    Sunday, Feb 5, 2023

  • 11:00 AM - Joe the Show
  • 2:30 PM - Oren Polak
  • 6:30 PM - Matty Q
  • 10:30 PM - Jay and Jim Show
  • La Te Da
    Sunday, Feb 5, 2023

  • 4:00 PM - Tea Dance
  • 8:30 PM - 3Sum - Piano Bar
  • More Live Entertainment

    Latest News

    Tune In to Musical Performances, Concerts and Music Festivals this Winter Season
    February 01, 2023

    The Florida Keys is an exciting destination for music lovers this season with a variety of musical performances, concerts and music festivals. The Studios of Key West, located on 533 Eaton St., is hosting renowned performers such as Libby York, Ama...

    Jimmy Buffett Concerts Set for Feb. 9 and 11 in Key West
    January 18, 2023

    Jimmy Buffett and The Coral Reefer Band are bringing their Second Wind Tour to Key West, Florida, with two performances scheduled for Thursday and Saturday, February 9th and 11th at the Coffee Butler Amphitheater in Truman Waterfront Park. Tickets go...

    7 Mile Offshore Grand Prix
    January 06, 2023

    Race World Offshore is set to bring offshore racing back to Marathon, FL after a 6 year hiatus with the Inaugural 7 Mile Offshore Grand Prix. Taking place April 28th - 30th, the racecourse will run alongside the Old Seven Mile Bridge, allowing specta...

    An Inspector Calls Kicks off 2023 at Waterfront Playhouse
    January 02, 2023

    The Waterfront Playhouse is proud to present a classic mystery, JB Priestley's An Inspector Calls. Starting January 12, the production will feature a stellar cast including Dan Waller, David Black, Barbara Mundy, Jillian Todd, J. Michael Wright, Arth...

    Handmade Works by Artisans to Highlight Key West Craft Show
    December 22, 2022

    Creative spirits will be showcased in Key West on the weekend of January 28-29. Attendees can explore the work of approximately 100 artisans from both the region and across the country at the 37th Annual Key West Craft Show. The show is free to the p...

    What's New in Key West for Winter 2022-23
    December 17, 2022

    2023 marks the 200th anniversary of Monroe County, and they are planning heritage activities to celebrate this milestone. In addition, Naval Air Station Key West is also celebrating their bicentennial with the Southernmost Air Spectacular featuring t...

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