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...
Key West Literary Seminar
Discover the 42nd Annual Key West Literary Seminar: “Family” Date: January 9–12, 2025Location: San Carlos Institute, 516 Duval Street, Key West, FL The Key West Literary Seminar returns for its 42nd year, inviting literature enthusiasts to explore the theme of “Family” with a lineup of 20 distinguished American and international authors. This four-day literary celebration promises a rich blend o...
Key West Half Marathon & 5K
Discover the 27th Annual Key West Half Marathon & Runfest! January 18–19, 2025 | Key West, FloridaExperience the ultimate destination race this winter! The 27th Annual Key West Half Marathon & Runfest invites thousands of runners from across the globe to bask in Key West’s warm January weather, race alongside the sparkling Atlantic Ocean, and immerse themselves in the vibrant culture of t...
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, ...
Upcoming Live Entertainment
Hog's Breath Saloon
Latest News
Florida Keys 2025: A Year of Unforgettable Adventures
If you're dreaming of a destination that blends tropical beauty with vibrant culture, the Florida Keys should top your 2025 travel list. With a calendar packed full of events ranging from quirky festivals to awe-inspiring spectacles, there’s always something to celebrate in this slice of paradise. Let’s dive into the highlights and discover what awaits in the Conch Republic. January: A Month of...
Groove and Sunshine: Key West’s Mile 0 Fest is a Must-See Musical Escape
Picture this: balmy breezes, turquoise waters, and five days of electrifying music that embodies the heart of Americana and “Red Dirt” soundscapes. Welcome to Mile 0 Fest, where the rhythms of the road meet the soul of the subtropics. Taking place January 21-25, this vibrant festival transforms the southernmost tip of the United States into a haven for music lovers. A Lineup That Rocks the Roots ...
Key West Scores Big: The 33rd Kelly McGillis Classic Brings Global Excitement to Paradise
Discover a Week of Competition, Camaraderie, and Culture in Vibrant Key West This January, the sun-soaked streets and crystal-clear waters of Key West will set the stage for an unforgettable event that blends adrenaline-pumping sports with the laid-back charm of this tropical paradise. The 33rd Kelly McGillis Classic International Women’s & Girls’ Flag Football Championship, running Januar...
Symphonic Nights in Paradise: Key West Welcomes the South Florida Symphony Orchestra
Escape to the enchanting island city of Key West, where music, culture, and coastal charm come together for an unforgettable experience. This season, the South Florida Symphony Orchestra, led by the visionary Maestra Sebrina Maria Alfonso, celebrates its 27-year legacy with a trio of spectacular performances sure to captivate music lovers of all kinds. Set against the backdrop of turquoise waters ...
Sail Into Paradise: The Southernmost Regatta Brings Thrills to Key West
Imagine the sun-kissed waters of Key West, the rhythmic snap of sails catching the wind, and the adrenaline-charged energy of world-class sailing teams battling it out. From January 20–25, this idyllic island—famous for its laid-back charm and subtropical beauty—will transform into a sailor's paradise as it hosts the Southernmost Regatta, a renowned international sailing event that promises exhila...
Reel in the Action: Key West Kingfish Mayhem Tournament 2025
Are you ready to test your angling skills in the pristine waters of the Florida Keys? The Key West Kingfish Mayhem Tournament, running from January 15–19, 2025, promises adrenaline-pumping competition, jaw-dropping catches, and some serious cash prizes. Whether you're a seasoned angler or just along for the ride, this event is the ultimate winter escape. Why Key West? Every year, the turquoise w...