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
Festival to Celebrate Stock Island's Seafaring Spirit, Arts and Cuisine
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
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
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
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
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
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...