Welcome
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 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
Day 1
- Ride the Conch Tour Train for an overview
- Photo at the Southernmost Point
- Visit Ernest Hemingway’s home
- Walk Duval St stopping at shops or bars of interest
- Watch the Sunset Celebration @ Mallory Square
- Walk Duval St for food & entertainment
The Historian
Day 1
- 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
Day 2
- Take a Walking Tour or Rent Bicycles
- Take a sunset sail on The Fury
Upcoming Events
Sunset Celebration at Mallory Square
Key West's world-famous Sunset Celebration takes place every evening at Mallory Square close to the foot of Duval Street. Featuring both renowned local and international artists and entertainers, the event invites visitors and locals alike to enjoy the sunset at water's edge. The event begins about two hours ahead of the sunset and ends soon after the sun sets. The performance takes place 365 days...
Florida Keys Seafood Festival
Experience Fresh Local Seafood and Live Music at the Florida Keys Seafood Festival The Florida Keys Seafood Festival is a premier two-day celebration held at Key West’s Truman Waterfront Park, where the local fishing community showcases the freshest catch in the Keys. This annual event, taking place on February 15th and 16th, offers a vibrant mix of culinary delights, live music, family-friendly ...
NAS Key West Airshow
Experience the Thrill of the Key West Air Show Featuring the Blue Angels The NAS Key West Southernmost Air Spectacular delivers high-flying excitement on March 29-30, 2025 at Naval Air Station Key West’s Boca Chica Field. This premier Key West air show features breathtaking aerial demonstrations by elite military and civilian performers, including the legendary U.S. Navy Blue Angels. Attendees en...
7 Mile Bridge Run
Experience the Iconic 44th Annual 7 Mile Bridge Run in the Florida Keys! The 44th Annual 7 Mile Bridge Run will take place on Saturday, April 5th, 2025, offering a breathtaking and unparalleled experience for runners worldwide. Participants will traverse the iconic 6.79-mile-long segmental bridge, stretching over the pristine waters of the Florida Keys and connecting Marathon to Ohio Key. This ex...
Conch Republic Independence Celebration 2025
The Conch Republic Independence Celebration 2024 marks its 42nd anniversary with a variety of events showcasing their unique heritage and vibrant culture. Celebrations begin on Friday, April 19th, with an opening ceremony at Mallory Square, including the raising of colors and a Conch Shell-Horn Salute, accompanied by live entertainment. This is followed by a kick-off party and a Conch Shell Blowin...
Key West Songwriters Festival
Experience the Magic of the 29th Annual Key West Songwriters Festival Discover the stories behind the songs at the 29th Annual Key West Songwriters Festival, the world’s largest celebration of its kind. Presented by BMI and Rams Head Promotions, this iconic event takes place April 30 - May 4, 2025, in the charming and intimate settings of Key West, Florida. Over the course of five unforgettable ...
Upcoming Live Entertainment
Hank's Hair of the Dog Saloon
Hemingway Distillery
Latest News
Florida Keys: A Music Lover’s Paradise Awaits
At The Studios of Key West, music takes center stage with rooftop concerts and intimate performances, including jazz vocalist Libby York, folk legend John McCutcheon, and bluegrass masters Henhouse Prowlers. Meanwhile, Impromptu Classical Concerts of Key West offers world-class ensembles like the Dover Quartet and rising star pianist Avery Gagliano at the historic St. Paul’s Episcopal Church. For...
Celebrate Tennessee Williams’ Legacy at the Key West Festival
If you’ve ever dreamed of immersing yourself in the world of a literary giant while soaking up the charm of an island paradise, the Tennessee Williams Key West Festival is calling your name. March marks the 114th birthday of Tennessee Williams, the legendary playwright behind A Streetcar Named Desire and Cat on a Hot Tin Roof. Williams called Key West home for more than 30 years, often crediting ...
Curtain Up! Florida Keys Theater Season Brings Magic to the Stage
The Florida Keys are known for their turquoise waters, stunning sunsets, and laid-back island vibe—but this year, they’re also a hotspot for top-tier theater. The 2025 performing arts season is packed with musicals, comedies, and dramas that promise to entertain locals and travelers alike. In the Upper Keys, The Key Players bring romance to the stage with Almost, Maine (Feb. 27–March 9), a charmi...
Key West’s “Conch Honk” Brings a Blast of Fun on March 8
Ever wanted to make music with a seashell? In Key West, they take that dream to a whole new level. On Saturday, March 8, locals and visitors alike will “blow their own horns” at the 62nd annual Conch Shell Blowing Contest, a quirky, only-in-the-Keys tradition that celebrates the island’s seafaring past. Blowing into a conch shell—pronounced “konk”—dates back centuries, once used by Native America...
Key West Orchid Festival: A Blooming Paradise Awaits Orchid Lovers
Calling all orchid enthusiasts and flower lovers alike—mark your calendars for the Key West Orchid Festival, happening Friday, Feb. 28, through Sunday, March 2, at the picturesque West Martello Garden Club, 1100 Atlantic Blvd. at Higgs Beach. This vibrant, three-day celebration of exotic and colorful orchids is a must-visit event in the Florida Keys. Whether you’re a seasoned grower or som...
Unlock the Secrets of Key West’s Hidden Gardens This February
Calling all garden lovers and tropical daydreamers! Imagine strolling through some of Key West’s most lush, private gardens, usually hidden behind charming fences and walls. Well, here’s your chance. The annual garden tours, hosted by the Key West Garden Club, are back on Friday and Saturday, February 21–22, and they’re offering you exclusive access to five stunning, one-of-a-kind spaces. Between...