JANUARY
Key West Theater, Key West | January 8 & 21, February 5 & 17, March 5 & 25, 2026 – See Ben Harrison Live in Concert
Ben Harrison’s concerts at the Key West Theater bring humor, personality, and original music together in a small, intimate setting.
A Peek Into Island Life: Audiences experience the island’s character through his witty anecdotes and songs inspired by local life. Older children and teens will enjoy the playful energy, while adults can appreciate the clever humor and rich storytelling.
Enjoy a Unique Point of View: Each performance feels personal, drawing the audience into the experience. It’s an opportunity to enjoy music and entertainment that is quintessentially Key West.
January 19 – 24 – Key West – The Southernmost Regatta
Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid sportsmanship during five consecutive days of racing. Competition is open to One Design and ORC Racing / Cruising Keelboats. Spectators can watch the races from various waterfront venues, mingle with sailors and view sailboats at the Galleon Resort’s marina, 617 Front Street, after each day’s races.
January 27 – 31- Jam Out at Mile 0 Fest – Key West
Families can enjoy five days of Red Dirt and Americana music at Mile 0 Fest, set against the island’s sun-soaked outdoor venues. A Welcoming Vibe: The festival blends lively performances with a laid-back atmosphere, giving everyone space to dance, sing, or just relax on the grass. Plenty to Eat: Food vendors and local shops add to the experience, so you can enjoy snacks and shop for unique items between sets.
January 28 – February 1 – Key West Food and Wine Festival
2026 Key West Food and Wine Festival. The Key West Food and Wine Festival is recognized as one of the best food and wine festivals in the country by the Travel Channel. If you’re a foodie, Key West is the place to be in January with over 20 unique events.
January 30 – 31 – Islamorada – 36th Annual Swamp Guides Ball Fishing Tournament & Auction
In this annual all-release competition, organized by the Florida Keys Fishing Guides Association, anglers target three species – bonefish, redfish and snook. The tournament benefits the Florida Keys Fishing Guides Foundation and the Guides Trust Foundation, organizations that provide funds to people in the local fishing industry in times of need. Guides are welcome to register and fish as anglers. Tournament activities take place at Safe Harbor Angler House, mile marker 80.5 bayside. The online auction is open to all, not just registered anglers.
White Street, Key West | Third Thursday of Each Month in 2026 – Enjoy Local Art at The Art Walk
The White Third Thursday Art Walk brings families into the heart of Key West’s creative scene.
A Range of Artistic Displays: Galleries, live demonstrations, and performance art make every turn interesting. Kids can explore visual and performance art while adults enjoy the works of painters, photographers, and jewelers.
Look Up at Local Architecture: The event is also a chance to see the island’s architecture and street life, adding to the experience. Enjoy the views of homes behind iconic picket fences, showcasing beautiful, coastal-chic designs.
Walking through the Art Walk offers a mix of discovery, creativity, and community energy for everyone in the family.
Stock Island, Key West | Second and Fourth Sundays of Each Month in 2026 – Explore Animal Lovers’ Paradise at the Animal Farm
Visiting the Monroe County Sheriff’s Animal Farm lets families meet a range of animals, from sloths and goats to birds and a capybara.
A Great Place for Kids: The farm has a welcoming atmosphere that encourages hands-on interactions. Children can feed animals and learn about their care, making the experience both fun and educational.
For Every Animal Lover: Parents can enjoy watching their kids connect with animals they don’t see every day. It’s a playful, memorable outing for animal enthusiasts of all ages.
FEBRUARY
Key West Theater, Key West | January 8 & 21, February 5 & 17, March 5 & 25, 2026 – See Ben Harrison Live in Concert
Ben Harrison’s concerts at the Key West Theater bring humor, personality, and original music together in a small, intimate setting.
A Peek Into Island Life: Audiences experience the island’s character through his witty anecdotes and songs inspired by local life. Older children and teens will enjoy the playful energy, while adults can appreciate the clever humor and rich storytelling.
Enjoy a Unique Point of View: Each performance feels personal, drawing the audience into the experience. It’s an opportunity to enjoy music and entertainment that is quintessentially Key West.
February 14 – 15 – Florida Keys Seafood Festival
Florida Keys Seafood Festival 2026 A two-day celebration of the bounty of the sea the 20th Annual Florida Keys Seafood Festival is Saturday, February 14th from 11:00 a.m. to 8:00 p.m. AND Sunday, February 15th from 11:00 a.m. to 5:00 p.m., at Truman Waterfront Park, Key West. There is a $10 admission charge per person.
Truman Waterfront Market, Key West | Every Thursday – Enjoy Local Produce at Truman Waterfront Farmers Market
Shopping at the Truman Waterfront Farmers Market is a colorful, engaging outing for families, letting kids learn what’s in season while connecting with members of the local community.
Something for Everyone: Fresh produce, ready-to-eat meals, and artisan goods line the stalls, giving visitors plenty to explore. Kids can enjoy tasting local snacks while adults browse crafts and meet local vendors.
Idyllic Vistas: The market’s waterfront location provides scenic views, making a stroll between stalls relaxing and enjoyable. It’s a place to connect with the community, discover new foods, and pick up one-of-a-kind souvenirs.
White Street, Key West | Third Thursday of Each Month in 2026 – Enjoy Local Art at The Art Walk
The White Third Thursday Art Walk brings families into the heart of Key West’s creative scene. A Range of Artistic Displays: Galleries, live demonstrations, and performance art make every turn interesting. Kids can explore visual and performance art while adults enjoy the works of painters, photographers, and jewelers.
Look Up at Local Architecture: The event is also a chance to see the island’s architecture and street life, adding to the experience. Enjoy the views of homes behind iconic picket fences, showcasing beautiful, coastal-chic designs.
Walking through the Art Walk offers a mix of discovery, creativity, and community energy for everyone in the family.
Stock Island, Key West | Second and Fourth Sundays of Each Month in 2026 – Explore Animal Lovers’ Paradise at the Animal Farm
Visiting the Monroe County Sheriff’s Animal Farm lets families meet a range of animals, from sloths and goats to birds and a capybara.
A Great Place for Kids: The farm has a welcoming atmosphere that encourages hands-on interactions. Children can feed animals and learn about their care, making the experience both fun and educational.
For Every Animal Lover: Parents can enjoy watching their kids connect with animals they don’t see every day. It’s a playful, memorable outing for animal enthusiasts of all ages.
MARCH
March 23 – Taste of Key West
Annual Taste of Key West! Join us for Taste of Key West 2026 at Truman Waterfront on Monday, March 23rd! This open-air event promises an assortment of beverages and palate-pleasing plates. Restaurants and food vendors from across the Lower Keys and Key West donate their staffs’ time and extraordinary culinary talents.
Key West Theater, Key West | January 8 & 21, February 5 & 17, March 5 & 25, 2026 – See Ben Harrison Live in Concert
Ben Harrison’s concerts at the Key West Theater bring humor, personality, and original music together in a small, intimate setting.
A Peek Into Island Life: Audiences experience the island’s character through his witty anecdotes and songs inspired by local life. Older children and teens will enjoy the playful energy, while adults can appreciate the clever humor and rich storytelling.
Enjoy a Unique Point of View: Each performance feels personal, drawing the audience into the experience. It’s an opportunity to enjoy music and entertainment that is quintessentially Key West.
White Street, Key West | Third Thursday of Each Month in 2026 – Enjoy Local Art at The Art Walk
The White Third Thursday Art Walk brings families into the heart of Key West’s creative scene.
A Range of Artistic Displays: Galleries, live demonstrations, and performance art make every turn interesting. Kids can explore visual and performance art while adults enjoy the works of painters, photographers, and jewelers.
Look Up at Local Architecture: The event is also a chance to see the island’s architecture and street life, adding to the experience. Enjoy the views of homes behind iconic picket fences, showcasing beautiful, coastal-chic designs.
Walking through the Art Walk offers a mix of discovery, creativity, and community energy for everyone in the family.
Stock Island, Key West | Second and Fourth Sundays of Each Month in 2026 –Explore Animal Lovers’ Paradise at the Animal Farm
Visiting the Monroe County Sheriff’s Animal Farm lets families meet a range of animals, from sloths and goats to birds and a capybara.
A Great Place for Kids: The farm has a welcoming atmosphere that encourages hands-on interactions. Children can feed animals and learn about their care, making the experience both fun and educational.
For Every Animal Lover: Parents can enjoy watching their kids connect with animals they don’t see every day. It’s a playful, memorable outing for animal enthusiasts of all ages.
APRIL
From April 17-26 Celebrate the 44th Anniversary of the Conch Republic Independence Celebration!
Experience ten unforgettable days packed with family-friendly festivities, vibrant local culture, and adventures on land and sea in historic Key West.
Start each day at the CRIC 2025 Welcome Center, located in the iconic Key West Historic Seaport, your hub for information and excitement throughout the event. Set sail aboard stunning historic schooners, including Danger Charters’ Danger’s Prize, the elegant America 2.0, or the luxurious catamaran Argo Navis. Enjoy thrilling snorkel trips, sunset sails, and unforgettable all-day sea adventures.
Kick off the celebrations on Friday, April 18th, at the lively Opening Ceremony at Mallory Square, featuring live music and a vibrant conch shell-horn salute. Later, don’t miss the famed Conch Shell Blowing Contest at Schooner Wharf Bar, where you’ll party with pirates under the stars!
On Saturday, April 19th, shop unique, locally-crafted treasures at the 41st Annual Conch Republic Art & Craft Duval Street Fair, or join the popular Conch Crawl Pub Stroll featuring cocktails at seven historic Key West saloons—complete with a collectible T-shirt! Later, cheer on flamboyant racers during the hilarious CR Drag Races on Duval.
Relax on Sunday, April 20th, at the charming KW Artisan Market at Higgs Beach, featuring local artists and specialty foods. Later, groove to world-class jazz at Jazz in the Gardens hosted by The Gardens Hotel’s enchanting wine gallery.
Don’t miss Hot Havana Night on Tuesday, April 22nd, at Kaya Island Eats. Salsa the night away with authentic Cuban cuisine, rum cocktails, and exciting auctions, all benefiting the TREE Institute International.
Witness a playful reenactment of the famous Great Sea Battle on Friday, April 25th, alongside Mallory Square. Watch from premier locations like Ocean Key Resort & Spa’s Sunset Pier, as the Conch Republic’s whimsical forces take on the US Coast Guard in this humorous maritime spectacle.
The celebration continues on Saturday, April 26th, with the quirky and colorful Julie Hansen Memorial Bed Races on Duval—a whimsical contest where decorated beds race for glory. Later that evening, enjoy thrilling boxing and wrestling action during Ricky Jackson’s Brawl on Duval.
Finally, celebrate sailing heritage during the 40th Annual Schooner Wharf Wreckers Cup Race Series on Sunday, April 27th, capped off with a festive awards party featuring a BBQ dinner and lively music.
The Conch Republic was established in 1982 as a tongue-in-cheek response to a U.S. Border Patrol blockade of the Florida Keys. Mayor Dennis Wardlow’s declaration of secession was a symbolic act of protest, embodying the community’s “Sovereign State Of Mind” and their spirit of independence. Today, these celebrations continue to foster a sense of unity and pride among the locals. Join thousands in this spectacular island event that perfectly blends humor, history, and Key West’s vibrant island spirit! Discover the full schedule of events, purchase early bird tickets, and grab exclusive merchandise at ConchRepublic.com.
April 29 – May 3 – Key West Songwriters Festival
The Key West Songwriters Festival is the largest festival of its kind in the world. The festival spans five days and nights, where songwriters introduce crowds to the faces, voices, and stories behind the songs! The festival takes place in Key West, Florida, at the most popular beaches, boats, bars, resorts, and Historic Theaters.
Stock Island, Key West | Second and Fourth Sundays of Each Month in 2026 – Explore Animal Lovers’ Paradise at the Animal Farm
Visiting the Monroe County Sheriff’s Animal Farm lets families meet a range of animals, from sloths and goats to birds and a capybara.
A Great Place for Kids: The farm has a welcoming atmosphere that encourages hands-on interactions. Children can feed animals and learn about their care, making the experience both fun and educational.
For Every Animal Lover: Parents can enjoy watching their kids connect with animals they don’t see every day. It’s a playful, memorable outing for animal enthusiasts of all ages.
White Street, Key West | Third Thursday of Each Month in 2026 – Enjoy Local Art at The Art Walk
The White Third Thursday Art Walk brings families into the heart of Key West’s creative scene.
A Range of Artistic Displays: Galleries, live demonstrations, and performance art make every turn interesting. Kids can explore visual and performance art while adults enjoy the works of painters, photographers, and jewelers.
Look Up at Local Architecture: The event is also a chance to see the island’s architecture and street life, adding to the experience. Enjoy the views of homes behind iconic picket fences, showcasing beautiful, coastal-chic designs.
Walking through the Art Walk offers a mix of discovery, creativity, and community energy for everyone in the family.
MAY
Stock Island, Key West | Second and Fourth Sundays of Each Month in 2026 – Explore Animal Lovers’ Paradise at the Animal Farm
Visiting the Monroe County Sheriff’s Animal Farm lets families meet a range of animals, from sloths and goats to birds and a capybara.
A Great Place for Kids: The farm has a welcoming atmosphere that encourages hands-on interactions. Children can feed animals and learn about their care, making the experience both fun and educational.
For Every Animal Lover: Parents can enjoy watching their kids connect with animals they don’t see every day. It’s a playful, memorable outing for animal enthusiasts of all ages.
White Street, Key West | Third Thursday of Each Month in 2026 – Enjoy Local Art at The Art Walk
The White Third Thursday Art Walk brings families into the heart of Key West’s creative scene.
A Range of Artistic Displays: Galleries, live demonstrations, and performance art make every turn interesting. Kids can explore visual and performance art while adults enjoy the works of painters, photographers, and jewelers.
Look Up at Local Architecture: The event is also a chance to see the island’s architecture and street life, adding to the experience. Enjoy the views of homes behind iconic picket fences, showcasing beautiful, coastal-chic designs.
Walking through the Art Walk offers a mix of discovery, creativity, and community energy for everyone in the family.
JUNE
June 3 – 7 – Key West Pride
2026 Dates – JUNE 3rd – 7th CELEBRATE ONE HUMAN FAMILY The Key West Pride event is one of the largest and most popular LGBTQ celebrations in the United States. Full of vibrant energy, spectacular events, and fun Key West activities, this is an event not to be missed.
Stock Island, Key West | Second and Fourth Sundays of Each Month in 2026 – Explore Animal Lovers’ Paradise at the Animal Farm
Visiting the Monroe County Sheriff’s Animal Farm lets families meet a range of animals, from sloths and goats to birds and a capybara.
A Great Place for Kids: The farm has a welcoming atmosphere that encourages hands-on interactions. Children can feed animals and learn about their care, making the experience both fun and educational.
For Every Animal Lover: Parents can enjoy watching their kids connect with animals they don’t see every day. It’s a playful, memorable outing for animal enthusiasts of all ages.
White Street, Key West | Third Thursday of Each Month in 2026 – Enjoy Local Art at The Art Walk
The White Third Thursday Art Walk brings families into the heart of Key West’s creative scene.
A Range of Artistic Displays: Galleries, live demonstrations, and performance art make every turn interesting. Kids can explore visual and performance art while adults enjoy the works of painters, photographers, and jewelers.
Look Up at Local Architecture: The event is also a chance to see the island’s architecture and street life, adding to the experience. Enjoy the views of homes behind iconic picket fences, showcasing beautiful, coastal-chic designs.
Walking through the Art Walk offers a mix of discovery, creativity, and community energy for everyone in the family.
JULY
July 1 – 5 – Key Lime Festival
Welcome to the Key Lime Festival: America’s Favorite Citrus Celebration! In the Florida Keys we like to celebrate the things that make our islands unique. Citrus, eccentrics, people & pie. Our celebrations are fun, odd & unforgettable. Our people are too. Come on down to the birthplace of Key Lime Pie for a little taste.
July 22 – 26 – Sloppy Joe’s Annual Hemingway Days
Hemingway Days 7/22/26 – 7/26/26 Key West’s Most Whimsical Tribute to Papa Hemingway Welcome to the Key West’s most iconic and whimsical tribute to one of the greatest literary figures of the 20th century, Ernest Hemingway. Held annually in sunny Key West, this event celebrates Hemingway’s life in Key West and enduring legacy.
Stock Island, Key West | Second and Fourth Sundays of Each Month in 2026 – Explore Animal Lovers’ Paradise at the Animal Farm
Visiting the Monroe County Sheriff’s Animal Farm lets families meet a range of animals, from sloths and goats to birds and a capybara.
A Great Place for Kids: The farm has a welcoming atmosphere that encourages hands-on interactions. Children can feed animals and learn about their care, making the experience both fun and educational.
For Every Animal Lover: Parents can enjoy watching their kids connect with animals they don’t see every day. It’s a playful, memorable outing for animal enthusiasts of all ages.
White Street, Key West | Third Thursday of Each Month in 2026 – Enjoy Local Art at The Art Walk
The White Third Thursday Art Walk brings families into the heart of Key West’s creative scene.
A Range of Artistic Displays: Galleries, live demonstrations, and performance art make every turn interesting. Kids can explore visual and performance art while adults enjoy the works of painters, photographers, and jewelers.
Look Up at Local Architecture: The event is also a chance to see the island’s architecture and street life, adding to the experience. Enjoy the views of homes behind iconic picket fences, showcasing beautiful, coastal-chic designs.
Walking through the Art Walk offers a mix of discovery, creativity, and community energy for everyone in the family.
AUGUST
August 5 – 9 – Key West Lobsterfest
Get Ready to Crack! Key West Lobsterfest 2026 Dates are Set! The wait is officially over! Get your butter warmers ready because we are thrilled to announce the dates for the biggest and tastiest summer celebration on the island: Key West Lobsterfest 2026 is happening from Wednesday, August 5th through Sunday, August 9th! Join us!
August 10 – 16 – Key West Rum Fest 2026
The Grand Tasting Event, held at the Key West Theater on Saturday, August 16, 3:30 – 5:30 pm. Savor an outstanding variety of rums from over 30 vendors, meet master distillers, and indulge in island cuisine. Tickets and event details are available at rumfestkeywest.com
Stock Island, Key West | Second and Fourth Sundays of Each Month in 2026 – Explore Animal Lovers’ Paradise at the Animal Farm
Visiting the Monroe County Sheriff’s Animal Farm lets families meet a range of animals, from sloths and goats to birds and a capybara.
A Great Place for Kids: The farm has a welcoming atmosphere that encourages hands-on interactions. Children can feed animals and learn about their care, making the experience both fun and educational.
For Every Animal Lover: Parents can enjoy watching their kids connect with animals they don’t see every day. It’s a playful, memorable outing for animal enthusiasts of all ages.
White Street, Key West | Third Thursday of Each Month in 2026 – Enjoy Local Art at The Art Walk
The White Third Thursday Art Walk brings families into the heart of Key West’s creative scene.
A Range of Artistic Displays: Galleries, live demonstrations, and performance art make every turn interesting. Kids can explore visual and performance art while adults enjoy the works of painters, photographers, and jewelers.
Look Up at Local Architecture: The event is also a chance to see the island’s architecture and street life, adding to the experience. Enjoy the views of homes behind iconic picket fences, showcasing beautiful, coastal-chic designs.
Walking through the Art Walk offers a mix of discovery, creativity, and community energy for everyone in the family.
SEPTEMBER
September 3 – 7 – Labor Day weekend
- Key West Brewfest: This multi-day event is a long-standing Labor Day tradition that features beer tastings, food, and music. It runs from Thursday through Labor Day Monday and includes more than 200 different beers from over 60 breweries.
- Just a Few Friends – Key West: This celebration of the life and music of Jimmy Buffett will take place from September 3–7, 2026. The event includes concerts, a parade, walking tours, and other activities. A source indicates that the festival will begin on a Thursday with a special event.
Stock Island, Key West | Second and Fourth Sundays of Each Month in 2026 – Explore Animal Lovers’ Paradise at the Animal Farm
Visiting the Monroe County Sheriff’s Animal Farm lets families meet a range of animals, from sloths and goats to birds and a capybara.
A Great Place for Kids: The farm has a welcoming atmosphere that encourages hands-on interactions. Children can feed animals and learn about their care, making the experience both fun and educational.
For Every Animal Lover: Parents can enjoy watching their kids connect with animals they don’t see every day. It’s a playful, memorable outing for animal enthusiasts of all ages.
White Street, Key West | Third Thursday of Each Month in 2026 – Enjoy Local Art at The Art Walk
The White Third Thursday Art Walk brings families into the heart of Key West’s creative scene. A Range of Artistic Displays: Galleries, live demonstrations, and performance art make every turn interesting. Kids can explore visual and performance art while adults enjoy the works of painters, photographers, and jewelers.
Look Up at Local Architecture: The event is also a chance to see the island’s architecture and street life, adding to the experience. Enjoy the views of homes behind iconic picket fences, showcasing beautiful, coastal-chic designs.
Walking through the Art Walk offers a mix of discovery, creativity, and community energy for everyone in the family.
OCTOBER
October 16 – 25 – Key West Fantasy Fest!
2026 Theme: Musical Icons & Iconic Musicals Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season.
Stock Island, Key West | Second and Fourth Sundays of Each Month in 2026 – Explore Animal Lovers’ Paradise at the Animal Farm
Visiting the Monroe County Sheriff’s Animal Farm lets families meet a range of animals, from sloths and goats to birds and a capybara.
A Great Place for Kids: The farm has a welcoming atmosphere that encourages hands-on interactions. Children can feed animals and learn about their care, making the experience both fun and educational.
For Every Animal Lover: Parents can enjoy watching their kids connect with animals they don’t see every day. It’s a playful, memorable outing for animal enthusiasts of all ages.
White Street, Key West | Third Thursday of Each Month in 2026 – Enjoy Local Art at The Art Walk
The White Third Thursday Art Walk brings families into the heart of Key West’s creative scene.
A Range of Artistic Displays: Galleries, live demonstrations, and performance art make every turn interesting. Kids can explore visual and performance art while adults enjoy the works of painters, photographers, and jewelers.
Look Up at Local Architecture: The event is also a chance to see the island’s architecture and street life, adding to the experience. Enjoy the views of homes behind iconic picket fences, showcasing beautiful, coastal-chic designs.
Walking through the Art Walk offers a mix of discovery, creativity, and community energy for everyone in the family.
NOVEMBER
Stock Island, Key West | Second and Fourth Sundays of Each Month in 2026 – Explore Animal Lovers’ Paradise at the Animal Farm
Visiting the Monroe County Sheriff’s Animal Farm lets families meet a range of animals, from sloths and goats to birds and a capybara.
A Great Place for Kids: The farm has a welcoming atmosphere that encourages hands-on interactions. Children can feed animals and learn about their care, making the experience both fun and educational.
For Every Animal Lover: Parents can enjoy watching their kids connect with animals they don’t see every day. It’s a playful, memorable outing for animal enthusiasts of all ages.
White Street, Key West | Third Thursday of Each Month in 2026 – Enjoy Local Art at The Art Walk
The White Third Thursday Art Walk brings families into the heart of Key West’s creative scene.
A Range of Artistic Displays: Galleries, live demonstrations, and performance art make every turn interesting. Kids can explore visual and performance art while adults enjoy the works of painters, photographers, and jewelers.
Look Up at Local Architecture: The event is also a chance to see the island’s architecture and street life, adding to the experience. Enjoy the views of homes behind iconic picket fences, showcasing beautiful, coastal-chic designs.
Walking through the Art Walk offers a mix of discovery, creativity, and community energy for everyone in the family.
November 26 weekend – Key West Thanksgiving
Thanksgiving Day in 2026 is on Thursday, November 26. While a full schedule for the holiday weekend has not yet been announced, events from previous years often repeat.
Check back as we move closer to the holiday for more information and schedules!
DECEMBER
Stock Island, Key West | Second and Fourth Sundays of Each Month in 2026 – Explore Animal Lovers’ Paradise at the Animal Farm
Visiting the Monroe County Sheriff’s Animal Farm lets families meet a range of animals, from sloths and goats to birds and a capybara.
A Great Place for Kids: The farm has a welcoming atmosphere that encourages hands-on interactions. Children can feed animals and learn about their care, making the experience both fun and educational.
For Every Animal Lover: Parents can enjoy watching their kids connect with animals they don’t see every day. It’s a playful, memorable outing for animal enthusiasts of all ages.
Enjoy Local Art at The Art Walk
White Street, Key West | Third Thursday of Each Month in 2026 – Enjoy Local Art at The Art Walk
The White Third Thursday Art Walk brings families into the heart of Key West’s creative scene.
A Range of Artistic Displays: Galleries, live demonstrations, and performance art make every turn interesting. Kids can explore visual and performance art while adults enjoy the works of painters, photographers, and jewelers.
Look Up at Local Architecture: The event is also a chance to see the island’s architecture and street life, adding to the experience. Enjoy the views of homes behind iconic picket fences, showcasing beautiful, coastal-chic designs.
Walking through the Art Walk offers a mix of discovery, creativity, and community energy for everyone in the family.
Christmas in Key West – A full schedule for 2026 is not yet available, but a few dates for the 2026 holiday season in Key West have been announced. Christmas Day falls on Friday, December 25, 2026.
| December 21–26, 2026 | A Road Scholar-organized trip, “The Holidays in Key West,” is scheduled to take place. |
| December 25, 2026 | Christmas Day, which will include a “Christmas Ultimate Adventure” trip. |
| December 26, 2026 | Florida Keys Southernmost Car Club Holiday Classic Car Show. |
| December 31, 2026 | New Year’s Eve celebrations, including the annual Conch Shell Drop at Sloppy Joe’s Bar. |
- The Harbor Walk of Lights, where the Key West Historic Seaport is decorated with holiday lights.
- The Lighted Boat Parade, with decorated boats sailing past Sunset Key and Mallory Square.
- The Key West Christmas Parade on Duval Street, featuring floats and marching bands.
- The Lobster Trap Tree Lighting at a local seafood restaurant.