Day Sailing - Daydreamer & Coconut Cruises

Let's go sailing!!! Fun in the sun on Daydreamer catamaran Fun in the Sun on our Catamarans...
Daydreamer and Coconut!!!

Day Sailing to St. John or British Virgin Islands departing from St. Thomas, U.S. Virgin Islands

Children 12 and Under Receive a 50% Discount.  Children under 2 are Free.


Peter Bay

Daydreamer Catamaran Day Sailing

Daydreamer Catamaran Day Sailing

Full Day St. John Sail

9 am - 3:45 pm $130 + gratuity

One of the benefits our multihull boats is that they offer the combination of speed and comfort. This enables us to explore more of the uninhabited, barrier islands around St. John. We try to take you off the beaten path to show you some of those places you've dreamt about! Whether its snorkel instruction, serving you delicious food & beverages, or just telling tales, our dynamic crew will help make your day memorable, safe and fun.

Great sailing, lots of snorkeling and beachcombing, excellent service and food all combine to make this a great value and a fantastic day.

Full Day Sail To St. John Menu

Sandy Cay

Daydreamer Catamaran Day Sailing

Daydreamer Catamaran Day Sailing

Full Day Sail to Jost Van Dyke, British Virgin Islands

8 am - 4 pm $125 + $60 pp customs fees (subject to change) + lunch + gratuity Passport Required

For a truly unique trip, join us for our sail to one of the most unspoiled jewels of the Caribbean. Set sail from St. Thomas for one of the small cays between St. Thomas & St. John where a fantastic morning swim/snorkel await. From there we head to Jost! While the crew takes care of customs, guests enjoy the famous Foxy’s for lunch, shopping, & entertainment.

After lunch, we bid farewell to "town" and cruise to pristine White Bay. There you can enjoy the fun of the infamous Soggy Dollar Bar or Ivan's Beach Bar. Just relax and enjoy the beauty and quiet of this beautiful beach and lagoon while having a refreshing afternoon swim. Our sail home is a spectacular spinnaker run, making for a great way to finish off the perfect day.

Full Day Sail To Jost Van Dyke Menu

Snacks offered on afternoon cocktail sail on Daydreamer

Sunset sail on Daydreamer

Cocktail Sail

4:30 pm - 6:00 pm (Winter season) | 5:00 pm - 6:30 pm (Summer season) $60 + gratuity

End the day and start the evening by enjoying the scenery of some of our less traveled areas between St. Thomas and St. John while watching another beautiful sunset in paradise. Great sailing, hors d' oeuvres, cocktails, and music make this trip a must for everyone who comes to the islands!

Snacks include: assorted cheeses & crackers, fresh veggie crudite and dip; very open bar.


1/2 Day Snorkel Sail

1 pm - 4 pm $80 + gratuity

This trip offers a nice taste of our waters without taking up your whole day. We sail to the coast of an uninhabited island, for excellent snorkeling amongst beautiful tropical marine life.

Snacks include: Fresh vegetable crudites with pretzels and dip; very open bar.

St John Trunk Bay

1/2 Day Sail with Lunch

Sunday, Tuesday - Friday

11 am - 3 pm or 12 pm - 4 pm  $105 + gratuity

Wake up late and still be on time to enjoy plenty of great sailing to beautiful St. John. Lie on the beach, swim, snorkel, or read a book on’s your day! Includes our Caribbean style buffet lunch and open bar.

1/2 Day Sail with Lunch Menu

***Please note: All day sails depart from the beach at the Sugar Bay Resort & Spa on St. Thomas, U.S. Virgin Islands. With private charters, we may be able to arrange a pick up location more convenient to your party.

(If passenger minimums are not met, all sails are subject to cancellation.)