Offering exclusive private sailing charters on your choice of great classic boats.
Sunset Sail Key West is a small, locally-owned fleet of sailboats and sailors in beautiful Key West, Florida.
We love sailing, and that’s what we’re here to do! Join us on one of our boats and experience the Florida Keys from the best place you can-out on the water! We depart daily from Key West and Stock Island on our authentic sailing vessels.
It’s not just about sunset sails either! Come sailing with us to snorkel the backcountry, have your wedding or private party, or see anything form the sunrise to the full moon.
Enjoy a Day Sail On Our Custom Sloop High Tide
High Tide Sailing Along Nicely
Choose From Our Fleet Of Classic Sailboats
Snorkel Gear Provided
Meet Our Fun Loving Crew!
Gourmet Cheese And Tropical Drink Add Ons
Local
Eat and Drink
- Classic Harbor Line - Key West (0.0 miles) - Dedicated to providing the most perfect hospitality and sailing experience one could find in Key Wes...
- Smokin Tuna Saloon - Key West (0.3 miles) - SMOKIN’ TUNA SALOON “There’s Something Fishy going On" The Best Kept Secret in Old Town Key...
- Key West Pub Crawl - Key West (0.3 miles) - Are you looking for the ultimate Key West tradition? Come along and do the “Duval Crawl™”. Key...
- Bone Island Haunted Pub Crawl - Key West (0.3 miles) - Are you ready for some "spirited" fun? Join us on a spine-tingling adventure through Bone Is...
- Bone Island Haunted Pub Crawl - Key West (0.3 miles) - Are you ready for some "spirited" fun? Join us on a spine-tingling adventure through Bone Is...
See and Do
- Classic Harbor Line Key West (0.0 miles) - Dedicated to providing the most perfect hospitality and sailing experience one could find in Key Wes...
- Classic Harbor Line Key West (0.0 miles) - Dedicated to providing the most perfect hospitality and sailing experience one could find in Key Wes...
- Sunset Sail Key West Key West (0.0 miles) - Offering exclusive private sailing charters on your choice of great classic boats. Sunset Sail Key We...
- Key Lime Bike Tours Key West (0.2 miles) - Cruising the best of Old Key West! Join us on a leisurely tour around historic Key West, the souther...
- Key West Pub Crawl Key West (0.3 miles) - Are you looking for the ultimate Key West tradition? Come along and do the “Duval Crawl™”. Key...
Shopping
- Smokin Tuna Saloon - Key West (0.3 miles) - SMOKIN’ TUNA SALOON “There’s Something Fishy going On" The Best Kept Secret in Old Town Key...
