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 [...]
September Serenity at the Key West Historic Seaport
September Serenity at the Key West Historic Seaport September in Key West carries its own kind of magic. At the heart of it all [...]
Summer Serenity at the Key West Historic Seaport – August 2025
Summer Serenity at the Key West Historic Seaport – August 2025 Key West, Florida is renowned for its vibrant culture, stunning sunsets, and [...]
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 [...]
Set Sail Through History: The Historic Seaport Sail | Harry S. Truman in Key West
Set Sail Through History: The Historic Seaport Sail | Harry S. Truman in Key West January 10, 2025 | 10:00AM-12:00PM CALLING ALL [...]
Romantic Escapade: A Valentine’s Day Guide to Key West Historic Seaport 2024
Romantic Escapade: A Valentine's Day Guide to Key West Historic Seaport 2024 Valentine's Day is just around the corner. Whether you're spending [...]
A Valentine’s Day to Remember at The Key West Historic Seaport
A Valentine's Day to Remember at The Key West Historic Seaport 2023 Valentine's Day is just around the corner. Whether you're spending the day [...]
The Southernmost Regatta powered by Sailing Inc.
The Southernmost Regatta offers 5 consecutive days of high-quality racing on the picturesque blue waters of Key West, FL. The event is open to One [...]
Dolphin Watch by Honest Eco®
- Environmental Educators - Sustainable Nature Tours - First Wild Dolphin Watch in the Florida Keys - First to remove single-use plastic water bottles [...]
Jolly II Rover
Come sail Key West’s most photographed ship – the Jolly II Rover, a square rigged topsail schooner! A Key West sailing adventure aboard the [...]