Our Boats

Sailing St. ThomasDaydreamer & Coconut Cruises has evolved from it’s inception in 1989. Today we are still operating and offering the widest variety of day sail charters available, on our totally remodeled trimaran Coconut and our custom built catamaran Daydreamer. We are proud to have the best crew and captains in the Caribbean. They have been with us for many years and take great pride in combining safety, professionalism and outstanding customer service. Our main goal is to provide our guests with the very best day of their vacation. Over the years we have had the pleasure of sailing these waters and meeting thousands of interesting people who live and visit here, helping us create and provide unique trips maximizing the Caribbean experience for our guests. We are truly blessed.

Our original philosophy remains the same... Provide a memorable experience on a first class boat, with first class service in a professional, FUN manner. It is our mission to make sure your time with us is better than you could imagine!

Thanks in advance for choosing us. I guarantee you will have a great time on any and all of our trips!

~ Diane Davis


  • Fresh water shower
  • Clean and comfortable restrooms
  • Easy access boarding ladders
  • Quality snorkel gear
  • Floatation devices
  • Very open bar
  • Daydreamer’s waterslide!!!!
  • Plenty of space and comfort!

Daydreamer day sailing

Daydreamer is a custom built 55’ catamaran USCG/SOLAS certified for 49 passengers. She has enormous space, very comfortable seating, custom bar/galley, a large clean and comfortable restroom, and our original trademark waterslide! She is also a great sailing machine with over 1300 sq.ft of working sail area! You can sail at 14 knots and never spill your drink!

Coconut Day Sailing

Coconut is a customized 50’ Newick trimaran USCG certified for 41 passengers. She offers lots of cushioned seating, her cockpit is fitted with tables and a shade awning that can provide shade over 2/3 of the boat.  Our great “sugar scoop” allows for super easy access to the water.  On any given day she gives our larger boat a run for the money when it comes to speed and comfort.