Three people sitting on a sailboat at sunset near Casa Morada, our resort in Islamorada.

Float Away in the Florida Keys

Whether you want to set forth on your own paddleboard or if a chartered cruise on one of our beautiful boats is more your style, we understand that being in the Keys is synonymous with being on the water. Activities in the Keys are all about salt-kissed breezes and sea-splashed memories. Explore the beautiful, crystal blue seas surrounding our private island or venture afar to spot our manatee neighbors with our exclusive sailing offerings.

About Sol Sister: Our beloved Sol Sister is a 32 ft. 'Baby' Chesapeake Bay Skipjack. She was built by hand in Maine in 1982 and has recently undergone a full renovation. She has called Casa Morada home since 2003. She can comfortably seat up to 6 passengers alongside her two-person crew, and she has a spacious and beautiful forward aft space that is ideal for a shared cocktail, chilled bottle of wine, and snacks while you sail. Designed to navigate the shallow waters of Chesapeake Bay, these powerful boats were traditionally used to haul fishing nets and oyster dredges. They were used regularly until the 1980s, when motorized boats finally took over. As a custom-made vessel, the Sol Sister is truly one of a kind and features classic lines, a smooth ride, and cuts through the water beautifully. She is available for reservations for sunset cruises as well as day sailing adventures, which can include lunch and a refreshing swim.

Set Sail on the Sol Sister

In the Keys, sunsets are real showstoppers. Islamorada sunsets are world famous, and there is no better way to explore them than on our beautiful historic sailing boat, the Sol Sister. We offer sailing excursions for two hours for up to 6 people, or hire our entire boat for a private cruise for you and your sweetheart. Captain Bill and first mate Elle will love to show you their favorite spots around the Keys and will enchant you with their seafaring tales.
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Boats moored on the shore at Casa Morada with clear skies, palm trees, and calm sea in the background.

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