Discover the essence of the holidays in Key West with our overview guide. Find all the key festive events and activities. Whether Key West is your backyard or a new adventure, our guide brings you the best of the holidays.
One of the standout attractions this season is the Key West “Bight” before Christmas® Celebration, where the waterfront transforms into a dazzling display of lights and local art. You can also wander along the enchanting Key West Harbor Walk of Lights, illuminated with an array of vibrant decorations that perfectly capture the island's festive spirit. And the Key West Holiday Historic Inn Tour is something you definitely don't want to miss, offering a glimpse into the charm of decorated inns steeped in history. See more details on these and other fun events and activities below!
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Top Holiday Events In and Around Key West
- Key West Harbor Walk of Lights
- Key West “Bight” before Christmas® Celebration
- Annual Lighting of the City Christmas Tree
- Key West Holiday Historic Inn Tour
- Annual Custom House Holiday Concert & Bazaar
- Wesley House Family Services’ Annual Holiday Village & BeLighted Bike Ride
- Holiday Tours on the Trolley
- Key West Triathlon
- Key West Lighted Boat Parade
- Fury’s Annual Sunset Sail with Santa
See these and even more events listed below!
Key West Holiday Light Displays
Key West “Bight” before Christmas® Celebration
What to Expect:
Holiday light displays and maritime-themed decorations.
Description:
The Key West “Bight” before Christmas Celebration features a spectacular display of holiday lights and creative displays around the Key West Bight Marina and Historic Seaport. Enjoy thousands of lights honoring maritime history, live music, and festive activities.
Where: Key West | More Info: Key West “Bight” before Christmas® Celebration
Key West Harbor Walk of Lights
What to Expect:
Nautical-themed holiday lights and decorations along the Key West waterfront.
Description:
The Key West Harbor Walk of Lights is a nautical-themed holiday display honoring the maritime history of Key West. The event features tens of thousands of lights, dozens of lighted palm trees, a lobster trap holiday tree, and a nautically decorated pine tree adorned with fishing buoys that resemble giant ornaments.
Where: Key West | More Info: Key West Harbor Walk of Lights
Key West Holiday Historic Inn Tour
What to Expect:
Guided tours of historically decorated homes.
Description:
Explore Key West's historic inns during the holiday season with guided tours that highlight beautifully decorated homes and festive traditions.
Where: Key West | More Info: Key West Holiday Historic Inn Tour
Annual Lighting of the City Christmas Tree
What to Expect:
Illumination of the city's Christmas tree with festive music and decorations.
Description:
The Annual Lighting of the City Christmas Tree is a cherished tradition where the city's Christmas tree is illuminated, accompanied by holiday music and festivities at Bayview Park, presented by First Horizon Foundation.
Where: Key West | More Info: Annual Lighting of the City Christmas Tree
Holiday Tours on the Trolley
What to Expect:
Guided tour of Key West's elaborately decorated homes and neighborhoods.
Description:
Explore Key West's beautifully decorated homes and neighborhoods on a guided holiday lights tour. Enjoy special holiday lights glasses and neighborhood caroling as you take in the island's festive atmosphere.
Where: Key West | More Info: Holiday Tours on the Trolley
Key West Lighted Boat Parade
What to Expect:
Synchronized light and sound show on historic boats.
Description:
The Key West Lighted Boat Parade features a maritime parade route illuminated by creative light displays, showcasing nautical creativity and festive spirit.
Where: Key West | More Info: Key West Lighted Boat Parade
Key West Holiday Markets and Shopping
Monthly Artisan Market
What to Expect:
Unique local crafts and live entertainment.
Description:
The Key West Artisan Market is a vibrant event showcasing local artisans and vendors. It features handmade arts and crafts, unique jewelry, clothing, home goods, and more. The market includes culinary delights, fresh produce, and live entertainment, creating a diverse and engaging experience for both locals and tourists.
Where: Key West | More Info: Monthly Artisan Market
Key West Holiday Shows and Entertainment
Annual Custom House Holiday Concert & Bazaar
What to Expect:
Holiday light show on historic Custom House.
Description:
The Annual Custom House Holiday Concert & Bazaar features Key West's finest artisans, musicians, and choirs, along with a holiday light show by Key West High School’s Conch 5 Studios. The event offers a treasure trove of unique gift items, live holiday music, and festive libations.
Where: Key West | More Info: Annual Custom House Holiday Concert & Bazaar
Coast is Clear Music Festival
What to Expect:
Intimate music sessions at historic venues.
Description:
The COAST Is Clear Music & Arts Festival is a locally and independently produced cultural celebration in Key West, featuring intimate shows, unforgettable sessions, and iconic local hangouts. The event includes a sandlot baseball tournament, classic Old Town park activities, surprise late-night sets, and performances at world-famous and off-beaten-path venues. It is held in the historic Bahama Village section of Old Town, Key West, and offers a laid-back weekend experience.
Where: Key West | More Info: Coast is Clear Music Festival
Key West Other Holiday Activities
Wesley House Family Services’ Annual Holiday Village & BeLighted Bike Ride
What to Expect:
Family-friendly holiday celebration with bike ride and obstacle courses.
Description:
The Wesley House Family Services’ Annual Holiday Village & BeLighted Bike Ride is a family-friendly event featuring photos with Santa, community booths with games and crafts, food booths, music, and local performances. The event includes two large holiday-themed inflatable obstacle courses for kids and a bike ride that follows the same route as the Fantasy Fest Parade.
Where: Key West | More Info: Wesley House Family Services’ Annual Holiday Village & BeLighted Bike Ride
Key West Triathlon
What to Expect:
Challenging multi-sport event with diverse distances.
Description:
The Key West Triathlon is a premier triathlon event featuring various distances, including international, duathlon, aquabike, and long sprint triathlons. Held at Higgs Beach, this event promises a challenging yet rewarding experience for athletes.
Where: Key West | More Info: Key West Triathlon
Fury’s Annual Sunset Sail with Santa
What to Expect:
Family-friendly holiday sail with Santa and festive drinks.
Description:
Join Fury's Annual Sunset Sail with Santa for a holiday celebration on the waters of Key West, featuring complimentary beer, wine, and snacks, and a special appearance by Santa.
Where: Key West | More Info: Fury’s Annual Sunset Sail with Santa
Christmas Ultimate Adventure H2.0
What to Expect:
Action-packed water sports and snorkeling in a state-certified ocean waterpark.
Description:
Embark on a thrilling 3.5-hour adventure in Key West with Fury's Ultimate Adventure H2.0. This action-packed tour includes reef snorkeling, parasailing, jet skiing, a banana boat ride, and access to Florida's only state-certified ocean waterpark. Enjoy refreshing snacks and beverages throughout the day.
Where: Key West | More Info: Christmas Ultimate Adventure H2.0
Waterfront Winter Wonderland
What to Expect:
Custom ice skating rink with thrilling rides and festive celebrations.
Description:
The Waterfront Winter Wonderland at the Coffee Butler Amphitheater in Key West features an ice skating rink, games, rides, attractions, music, and light displays. The event includes themed skate nights, live music performances, and special holiday experiences like photo opportunities with Santa and crafts.
Where: Key West | More Info: Waterfront Winter Wonderland
Hometown Holiday Parade
What to Expect:
Charming hometown parade with holiday floats and Santa's appearance.
Description:
The Key West City Hometown Holiday Parade is a free event featuring holiday floats, tons of kids of all ages, and a guest appearance by Santa. The parade starts at Truman Avenue and White Street, then proceeds down Duval Street to Eaton Street.