Enjoy a private sunset sail near St. John with Calypso Charters, where vibrant Caribbean sunsets and crystal-clear waters create an unforgettable experience. Perfect for relaxing or celebrating in style.
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for all fitness levels; minimal physical exertion required.
Wildlife
History
St. John has a rich colonial history that influenced the island’s cultural heritage and maritime traditions.
Conservation
Calypso Charters practices eco-friendly sailing and supports marine conservation efforts in the Virgin Islands.
Calypso Charters
Enjoy a private sunset sail near St. John with Calypso Charters, where vibrant Caribbean sunsets and crystal-clear waters create an unforgettable experience. Perfect for relaxing or celebrating in style.
Calypso Charters is a Saint John–based boat operator offering day sails and private charters in the U.S. and British Virgin Islands. Operating from Saint John's, Saint John, Calypso Charters runs three signature experiences: the Calypso - Jost Van Dyke Sail (an 8-hour sailing adventure), A Trip to LimeOut (a 7-hour day trip), and the CAT 5 private charter aboard a 36’ power catamaran with capacity for up to 12 guests.
Each full-day trip includes on-board amenities described in the trip summaries: continental breakfast and an open bar are provided on select departures, snorkeling stops at prime reef locations, and beach time at White Bay and other St. John beaches. The Jost Van Dyke sail features breakfast, snorkeling, Great Harbor exploration, and time in White Bay. The LimeOut trip focuses on remote barrier island snorkeling, tacos and craft cocktails at LimeOut, and beach access. The CAT 5 private charter offers a customizable itinerary, sunbathing on bean bag chairs, and a smooth ride for small groups.
Calypso Charters emphasizes personalized private charters and small-group day trips. Guests booking the CAT 5 can expect a maximum of 12 passengers, enabling an intimate experience and flexible route planning. Departure point is Saint John's, Saint John, providing convenient access for visitors to St. John and nearby islands. Trip durations are listed per experience, with the Calypso - Jost Van Dyke Sail running approximately eight hours and A Trip to LimeOut about seven hours; private CAT 5 charters are scheduled based on customer selection. Detailed itineraries, on-board inclusions, and vessel information are provided on the listing to help travelers make an informed booking decision on The Adventure Collective.
Departure
Saint John's, Saint John
Local departures from St. John
Trip Durations
7–8 hours
Day trips to nearby islands
Vessels
Calypso & CAT 5 (36’)
Power catamaran and sailing options
Private Capacity
Up to 12 guests
Intimate private charters available
Reserve the Calypso - Jost Van Dyke Sail, A Trip to LimeOut, or the CAT 5 private charter today — clear itineraries and vessel details make booking simple.
Bring Reef-Safe Sunscreen
Protect your skin and marine life by choosing environmentally safe sunscreen for the sail.
Arrive Early to Explore
Plan to arrive 30 minutes before departure to settle in and enjoy the dock area’s views.
Stay Hydrated
Evenings on the water can be warm – bring water bottles to stay refreshed onboard.
Secure Footwear Recommended
Wear sandals or shoes with good grip, as boat decks can be slippery when wet.
Reef-Safe Sunscreen
Protects your skin and the ocean ecosystem during your sail.
summer
Light Jacket or Windbreaker
Keeps you warm as evening ocean breezes pick up near sunset.
fall
Polarized Sunglasses
Reduces glare and enhances your view of the sparkling sea.
Non-Slip Boat Shoes
Improves safety when moving on wet deck surfaces.