Raise Your Glass: St. Patrick’s Day 2026 At The Key West Historic Seaport
Raise Your Glass: St. Patrick's Day 2026 at the Key West Historic Seaport Celebrate St. Patrick’s Day at the Key West Historic Seaport 🍀 If you’re looking for a uniquely tropical way to celebrate St. Patrick’s Day, the waterfront at the Key West Historic Seaport offers the perfect blend of Irish tradition and laid-back island fun. With live music, festive drinks, waterfront dining, and lively celebrations throughout the district, it’s one of the best places in Key West to spend March 17. Here are some of the best ways to enjoy St. Patrick’s Day at the Key West [...]
⛵Schooner Wharf Wreckers Cup Race Series + Open Air Art & Music Affair 💙
⛵Schooner Wharf Wreckers Cup Race Series + Open Air Art & Music Affair 💙 Schooner Wharf Bar Wrecker's Cup Race Series  Ladies and Gentlemen: Start your sails! The second race of the popular and much anticipated Schooner Wharf Bar Wrecker's Cup Race Series is set for Sunday, February 22! Come meet fellow sailors, enjoy a fun day on the water and celebrate the “victor’s spoils” with us. All entries qualify for a chance to win a $400 Custom Made Helm Saddle courtesy of C Cushions out of Bacliff, Texas! The Captains Meeting is held Saturday, February [...]
Ideas For a Lovely Valentine’s Day at The Key West Historic Seaport
Ideas For a Lovely Valentine's Day at The Key West Historic Seaport 💝 Fall in Love at the Key West Historic Seaport This Valentine’s Day Looking for a Valentine’s Day that feels magical, memorable, and unmistakably Key West? Make your way to the Key West Historic Seaport—the ultimate waterfront destination for celebrating love in style. With world-class dining, live music, unique shops, and breathtaking harbor views, the Seaport sets the perfect backdrop for your Valentine’s Day plans. 🌅 Waterfront Romance with Island Vibes Stroll the historic docks, feel the sea breeze, and enjoy unforgettable sunset views—the kind that [...]
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: Why January Is the Perfect Time to Experience the Key West Historic Seaport January in Key West is a breath of fresh ocean air—and there’s no better place to soak it in than the Key West Historic Seaport. As the holiday crowds thin and the island settles into its most comfortable rhythm, the Seaport comes alive with cool breezes, golden sunsets, and authentic Old Key West charm. Perfect Weather for Waterfront WanderingJanuary brings some of [...]
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 Cates, a near lifelong resident of Key West who had a passion for serving others. The mission of the Cheryl Cates Memorial Foundation is to assist families and children in need in Monroe County, Florida and improve their quality of life by making grants directly to them and other charitable organizations in order to meet needs that are not otherwise being addressed. Cheryl Hollon Cates was born in 1953 in Jacksonville, Florida. At the age [...]
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 corner, and there’s no better place to experience it than at the Key West Historic Seaport! The waterfront will once again sparkle with thousands of twinkling lights, festive décor, and that unmistakable island cheer during the annual Lighting of the Harbor Walk of Lights, which kicks off the variety of Bight Before Christmas celebrations starting from Thanksgiving and lasting all the way through the new year! 🌴 A Key West Holiday Tradition Each year, the [...]