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 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, ...
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...
Upcoming Live Entertainment
Hank's Hair of the Dog Saloon
Hog's Breath Saloon
Irish Kevin's
Latest News
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...
Taste the Ocean’s Bounty: Dive into the Florida Keys Seafood Festival
If the idea of feasting on the freshest seafood while celebrating the hardworking fishermen who harvest it excites you, then mark your calendar for the 19th Annual Florida Keys Seafood Festival. This vibrant weekend event, held on February 15-16, offers a true taste of the ocean alongside lively music, arts, and a slice of Keys culture. Highlights of the Festival Set against the picturesque back...
Step Back in Time: Presidential Families Weekend at Key West’s Little White House
Discover History, Heritage, and Charm This Presidents Day This Presidents Day weekend, journey to Key West, Florida, for an unforgettable experience that merges history, heritage, and tropical charm. From February 13 to 17, the iconic Harry S. Truman Little White House will host Presidential Families Weekend, a captivating series of events celebrating America’s storied past and the preservation o...
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...