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...
Southernmost Regatta
Experience the Excitement of The Southernmost RegattaJanuary 20–25 | Key West, FloridaVisit: southernmostregatta.com The Southernmost Regatta is a premier sailing event bringing together elite sailing teams from around the globe to compete in the stunning azure waters off Key West, Florida. Over five consecutive days of exhilarating races, vibrant sails, and unmatched sportsmanship, this regatta ...
Mile 0 Fest
Experience Five Unforgettable Nights of Music in ParadiseJanuary 21st - January 25th, 2025 Mile 0 Fest Key West invites music enthusiasts to indulge in a spectacular boutique festival where the rhythms of Red Dirt and Americana music meet the serene beauty of Key West. This premier annual event combines stellar performances by iconic and emerging artists with the island’s relaxed, vibrant atmosph...
Key West Food & Wine Festival
16th 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 locations. Over 20 unique events including waterfront tastings, winemaker/chef collaborations and local funky events that present an authentic taste of Key West, Florida The place to be in January, ...
Florida Keys Seafood Festival
Dive into the vibrant world of the Florida Keys Seafood Festival, a two-day extravaganza held at Key West’s Truman Waterfront Park on February 15–16, 2025. This annual event, now in its 19th year, is a joyous celebration of the local fishing community, offering attendees an unforgettable experience filled with the freshest seafood, lively entertainment, and family-friendly activities. A Seafood L...
NAS Key West Airshow
Experience the Thrill of the NAS Key West Southernmost Air Spectacular! March 29-30, 2025 | Naval Air Station Key West, Boca Chica FieldPrepare for a weekend of breathtaking aerial performances, featuring military and civilian acts, at the NAS Key West Southernmost Air Spectacular. This highly anticipated event offers free general admission and showcases the U.S. Navy Blue Angels alongside a stel...
Latest News
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...
Dive into Key West’s Sunken History at the Mel Fisher Maritime Museum’s Winter Lecture Series
Looking for a unique reason to head to Key West this winter? The Mel Fisher Maritime Museum is hosting a fascinating lecture series that’s perfect for history buffs, treasure enthusiasts, and curious travelers alike. From Spanish galleons loaded with treasure to tales of emancipation and the maritime slave trade, this series promises to uncover the rich and complex stories that make the Fl...
Celebrity Jeopardy! Shines the Spotlight on the Florida Keys’ Conch Republic
Get ready to buzz in, trivia fans! The Florida Keys’ quirky and beloved "Conch Republic" recently stole the show on the newest season of Celebrity Jeopardy!, and it's got everyone talking about this slice of paradise. The episode, which aired on January 8, marked a fabulous opportunity for the "micronation" to flaunt its charm, history, and colorful cast of characters. A Spotlight on Trivia and T...
Key West Art and Craft Festival: A Colorful Weekend by the Waterfront
If you’re dreaming of an artsy getaway surrounded by sun, sea, and creativity, mark your calendars for February 22-23. The Key West Art and Craft Festival is set to transform the picturesque Truman Waterfront Park into an open-air gallery, offering visitors a delightful mix of artistic treasures, food, and tropical vibes. From 10 a.m. to 5 p.m. each day, the scenic boardwalk at the end of Southar...
Celebrate Hemingway's Legacy at Key West's Whimsical Look-Alike Extravaganza!
If Ernest Hemingway were alive today, where would he be? Chances are, he'd be raising a toast at Sloppy Joe's Bar during the 44th Annual Hemingway Look-Alike Contest in Key West, Florida. From July 23-27, 2025, this charming island city transforms into a literary lover's paradise, teeming with camaraderie, humor, and Hemingway’s enduring spirit. Why This Event Should Be on Your Bucket List Wheth...