Don't miss this magical nautical display of holiday lights on board every manner of watercraft in Key West Harbor. The judges stand is located at Schooner Wharf, 202 William St. Viewing is available from all along the Harbor Walk. The parade starts at 8 p.m.
Join the fun at the Key West Artisan Market on select Sundays! Discover local artisans showcasing colorful handmade crafts, unique jewelry, and delicious treats. Enjoy live music, tasty bites from local food vendors, and soak up the festive island vibes. It’s the perfect place to support creativity and find one-of-a-kind treasures!
Discover the vibrant flavors and local treasures at the Key West Farmer's Market, held every Thursday at the Truman Waterfront Pier. Browse an array of stalls brimming with freshly harvested produce, artisanal goods, and handmade crafts, all crafted with passion by local vendors. Immerse yourself in the lively atmosphere, where the scent of ripe fruits mingles with the sounds of live music, creating an unforgettable experience for visitors and locals alike.
Come check out this festive event during your stay! Guests are encouraged to bring an unwrapped toy for the Monroe County Domestic Abuse Shelter. Classic cars from every era will be decked out for the holidays, hosted by the Florida Keys Southernmost Car Club in honor of founder Dick Moody. Non-member cars may even enter free with an unwrapped toy—making it a fun and meaningful outing for all.
The Southernmost Regatta event in Key West presents five days of exhilarating racing set against the stunning backdrop of the island's azure waters. Open to both One Design and ORC Racing/Cruising Keelboats, it provides a thrilling opportunity to compete on the open sea while immersing oneself in the vibrant island culture. As winter chills settle in elsewhere, participants can bask in the warmth of camaraderie, rekindling friendships amidst the excitement of competitive sailing.
Join the fun at the Key West Artisan Market on select Sundays! Discover local artisans showcasing colorful handmade crafts, unique jewelry, and delicious treats. Enjoy live music, tasty bites from local food vendors, and soak up the festive island vibes. It’s the perfect place to support creativity and find one-of-a-kind treasures!
17th 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 Florida Keys Seafood Festival is a vibrant celebration of the region's rich maritime heritage and culinary delights. Visitors can indulge in an array of freshly caught seafood, from succulent stone crab claws to delectable lobster tails, all prepared by local chefs with expert care. Amidst the lively entertainment and adult beverage offerings, visitors can savor a diverse selection of freshly prepared seafood dishes while perusing local crafts and enjoying the vibrant atmosphere, making it a must-attend event for seafood enthusiasts and culture seekers alike.
This Art Festival is a time-honored tradition dating back to the early 60’s when Old Island Days was a 10-week celebration of special events. The art show has grown to nearly 100 artists from near and far spreading up Whitehead Street and down onto Caroline Street into the beautiful Truman Annex residential gated community. Fine Craftsmen and Artists will be selected to show and sell their original work in beautiful Old Town Key West.
It’s Fun FOR ALL And ALL For FUN The 44th Anniversary of Our Independence! Calling Conch Republic Patriots, Pirates and Partiers – Declare Your FUN-dependence! Head to Key West’s 44th Annual Conch Republic Independence Celebration 2026. Conch Republic Days 2026 celebrates Key West’s One Human Family and the diversity of its Conch-stituents dedicated to bringing Humor, Peace and Respect […]
The Key West Songwriters Festival is the largest festival of its kind in the world, and known as a career starter for top country talent. The festival has kicked off the careers of household names such as Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser and Maren Morris. In its 29th year, […]
The City of Key West is hosting a free community celebration, “America’s 250th,” at Key West’s Truman Waterfront Park on Saturday, June 27, 2026 (5–10 p.m.) to mark the nation’s 250th anniversary.
The event includes a downtown patriotic parade, formal ceremony with honors for military, veterans, and first responders, and a live “Salute to America” music program featuring local performers. Attendees can also expect food and drink vendors, a children’s activity area, community booths, and a sunset waterfront celebration. Admission is free.