20th Annual Florida Keys Seafood Festival
20th Annual Florida Keys Seafood Festival FEBRUARY 15-16, 2026 Two Days of Seafood, Music & Family Fun Attend the 20th Annual Florida Keys Seafood Festival [...]
Mile 0 Fest 2026
Mile 0 Fest 2026 Key West Mile 0 Fest is a five-day Red Dirt and Americana music festival held every year in Key West, Florida, [...]
The Southernmost Regatta 2026
The Southernmost Regatta 2026 Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid [...]
New Year, Old Town Charm: Why January Is the Perfect Time to Experience the Key West Historic Seaport
New Year, Old Town Charm: Why January Is the Perfect Time to Experience the Key West Historic Seaport New Year, Old Charm: [...]
The Cheryl Cates Memorial Foundation And The Key West Holiday Season
The Cheryl Cates Memorial Foundation and The Key West Holiday Season The Cheryl Cates Memorial Foundation was founded in honor of Cheryl Hollon [...]
2025 Bight Before Christmas Festivities at Key West Historic Seaport Are Just Around The Corner!
2025 Bight Before Christmas Festivities at Key West Historic Seaport Are Just Around The Corner! The holiday season is just around the [...]
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 [...]
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 [...]
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 [...]
Bight Before Christmas Lighting of The Bight: Key West Harbor Walk of Lights 2025
Wednesday, Nov. 26 – Free The Lighting of the 2025 “Harbor Walk of Lights” at the Key West Historic Seaport Main Harbor Walk Lighting at [...]