The Southernmost Regatta – 2025
The Southernmost Regatta - 2025 Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid [...]
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2025 40th Annual Schooner Wharf Bar Wrecker’s Cup Race Series
2025 40th Annual Schooner Wharf Bar Wrecker’s Cup Race Series The much anticipated Schooner Wharf Bar Wrecker’s Cup Race Series is scheduled for the last [...]
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2025 40th Annual Schooner Wharf Bar Wrecker’s Cup Race Series
The 2025 40th Annual Schooner Wharf Bar Wrecker’s Cup Race Series The 2025 40th Annual Schooner Wharf Bar Wrecker’s Cup Race Series The much anticipated [...]
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NAS Key West Southernmost Air Spectacular March 29 and 30, 2025
The Blue Angels & other military & civilian acts will fill the skies of the Florida Keys March 29-30th, at the NAS Key West [...]
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43rd Annual Conch Republic Independence Celebration
43rd Annual Conch Republic Independence Celebration Get your tickets here!
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Key West Songwriters Festival 2025
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. [...]
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2025 Schooner Wharf Bar Minimal Regatta
2025 Schooner Wharf Bar Minimal Regatta Calling All Ship Wrights! Sunday, May 25, 2025 Minimal Regatta Construction Rules 1. One sheet of 4' x [...]
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Key West Pride 2025
KEY WEST PRIDE 2025! SPONSORED IN PART BY Celebrate PRIDE on a tropical island that is legendary for its laid-back style and its open and [...]
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Taste of The Keys
Taste the Keys is a month-long culinary celebration running October 1–31, showcasing delicious cuisine from some of the best restaurants in the Florida Keys. Enjoy [...]
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Just a Few Friends Key West 2025
Just a Few Friends Key West 2025 August 29 – September 1, 2025 A four-day island celebration honoring Jimmy Buffett’s legacy with live music, food, [...]
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Key West Fantasy Fest 2025
Key West Fantasy Fest 2025 - October 17-26, 2025! Fantasy Fest Background: Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in [...]
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Key West Powerboat Races – Race World OffShore
WAYS TO WATCH LIVE! Key West, FL – November 5th, 7th, & 9th, 2025 Race World Offshore is gearing up to deliver an unforgettable week [...]
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Bight Before Christmas Lighting of The Bight: Key West Harbor Walk of Lights 2025
At the 16’ Nautical Christmas Tree on the Harbor Walk of Lights at William St.Wednesday, Nov. 26 – Free The Lighting of the 2025 “Harbor Walk of Lights” at the Key West Historic Seaport Main Harbor Walk Lighting at [...]
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20th Annual Pet Pictures with Santa™ – Hosted by The All Animal Clinic
Thursday, December 4 – FREE to attend 6:00pm – 8:00pm 2025 Pet Pictures with Santa™ – Hosted by The All Animal Clinic Professional photos by [...]
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2025 Key West City “Hometown Holiday Parade”
Saturday, December 6 – FREE 2025 Key West City “Hometown Holiday Parade” Starts at 6:30pm LOCATION: Parade starts on Truman Ave. (at White St.) then proceeds [...]
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Schooner Wharf Bar 2025 Tree Trimming Party and Toy Drive
Sunday, December 7 – FREE to Attend Schooner Wharf Bar 2025 Tree Trimming Party and Toy Drive Starting at 6:00PM LOCATION: Schooner Wharf Bar and Galley [...]
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Schooner Appledore Lighted Boat Parade Party
Saturday, Dec. 13 Schooner Appledore Lighted Boat Parade Party 7:30pm – 9:30pm Be a participant in the 2025 The Lighted Parade aboard the Schooner Appledore [...]
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The 34th Annual Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade
The 34th Annual Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade sails into the holiday season on Dec. 13th. Key West’s Historic Seaport has been transformed [...]
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2025 “Holiday Classic Car Show” & Toy Drive
Conch Republic Seafood Company parking lot – on the Harbor Walk of Lights at Greene St.Sunday, December 21 The Florida Keys Southernmost Car Club presents 2025 “Holiday Classic Car Show” & Toy Drive FREE • 11:00am – 3:00pm LOCATION: Conch Republic [...]
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Lowering of the Pirate Wench at Midnight at Schooner Wharf Bar!
Lowering of the Pirate Wench at Midnight! LOCATION: Schooner Wharf Bar and Galley On the Harbor Walk of Lights at William St. Great Food, Holiday Drinks [...]