CasaMorada | Islamorada, Florida

Set Sail in the Caribbean Keys

Whether you want to set forth on your own paddle board or if a chartered cruise on one of our beautiful boats is more your style, we understand that being in Keys is synonymous with being on the water. Explore the beautiful crystal blue seas surrounding our private island or venture afar to spot our manatee neighbors with our exclusive sailing offerings.

Set Sail on the Sol Sister

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.

Private Two Hour Sail $400

Please contact the front desk to book.


Our beloved Sol Sister is a 32ft -“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 six 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.

Tour Islamorada on the Gypsy Soul

Experience the coastline with the newest addition to our marine family; our beautiful Gypsy Soul, a classic motor-launch.

Join us for a leisurely 2 hour tour of our coastline with our intrepid captain Bill Todd, a sailor, marine environmentalist, local history buff and longtime Islamorada resident as he guides you through the history of the Florida Keys and the natural wildlife that graces our tropical locale. Islamorada is best viewed from the water, and the Gypsy Soul is a wonderful vessel from which to view it. 

Enjoy beautiful waterfront homes, historic places, and even experience the Florida Keys National Marine Sanctuary, where dolphins, turtles, and manatees are frequent visitors. The Gypsy Soul provides a comfortable berth from which to experience the best of what the keys have to offer, and and is shaded for a comfortable and cool ride. Add a picnic to your adventure, or a swim at the nearby Coral Garden for a perfect day on the water.

Price:  $300 / 2 hours