Sunset Cruise from Islamorada in the Florida Keys | Island Tours

Book a Sunset Cruise in Islamorada

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Take a Sail Or Tour the Island!

Our Customized Boat Tours with Captain Bill and Elle begin at 10:00 am daily and depart at your convenience.

Let us know what you would like to do and when you’d like to leave.

Kayaks Paddleboards are provided for our guests free of charge…

Sol Sister Sunset Sail…

Amazing Memories Sailing Nightly …

Islamorada Sunsets are world famous, and there’s no better way to experience one than aboard “Sol Sister”. Our 32ft Historic Skipjack, Sol Sister. The evening breeze with just the sound of water lapping by, there’s nothing quite like it. Hundreds of our guests have raved about it and return time and again. Your hosts Capt. Bill and First Mate Elle are standing by for your sunset sailing (or day sailing!) pleasure. Reserve your spot by contacting the concierge desk.

Two Hour Sunset Sail $300 per couple
Private Two Hour Sail $400

Sol Sister sunset sail

People riding Sol Sister during sunset


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 lived at Casa Morada since 2003.

Sol Sister has been modified to comfortably seat up to 6 passengers and features a small dining area forward just perfect for snacks and drinks.

Designed for the shallow waters of Chesapeake Bay, these powerful boats were used to haul fishing nets and oyster dredges and were hard at work until the 1980’s. Being custom made, she is truly one of a kind. With her historic lines, classic wide and smooth ride, Sol Sister is the perfect sailboat for the Florida Bay.

Sol Sister is also available for day-sailing adventures which can include lunch and a refreshing swim.

Sol Sister drawing
Skipjack plans


$300 / 2 hours

Your personalized Island-Tour adventure begins the newest addition to our Casa Morada Tours family, “Gypsy Soul” our Classic Motor-Launch.

Join us for a leisurely 2 hour tour of our coastline, presented in a compelling, clear and entertaining narrative by Master Captain, Bill Todd, Sailor, Marine Environmentalist, local history buff and longtime Islamorada resident.

Islamorada is best viewed from the water, and Gypsy Sol is the perfect vessel! You’ll enjoy the beautiful waters, the lovely waterfront homes, historic places and even experience the Florida Keys National Marine Sanctuary. She offers an excellent view, is comfortable and shaded for a cool ride. Make it a picnic with a swim at a nearby Coral Garden!

Island Tour adventure


$300 / 2 hours

There’s plenty of “Waterin’ Holes” & Restaurants on the waterfront. Visit them in style! The Islamorada Sandbar has become a famous place to see and be seen, located just minutes away from Whale Harbor Bridge.