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!
- Ride the Old Town Trolley
- Consider stopping at: Ernest Hemingway’s home, Lighthouse, Audubon house, Southernmost Point, Mel Fishers Museum
- Watch the Sunset Celebration @ Mallory Square
- Walk Duval Street for food & entertainment
Upcoming Live Entertainment
Tune In to Musical Performances, Concerts and Music Festivals this Winter Season
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
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
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
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
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
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...