Not quite sure of what to expect on your USVI crewed sailing charter? This charter vacation is “all about you”, as you set the pace and can choose to do as much or as little as you’d like. Your experienced crew will provide suggestions each day based on your group’s specific interests, what you’re up for that day, plus of course the weather at hand. The itinerary below is just a sample itinerary to provide you with a feel for what’s available on one of our USVI catamaran charters. Contact us to begin planning your USVI charter.

Day 1

12:00 pm - Pickup at American Yacht Harbour dock or Yacht Haven Grande Marina in St. Thomas (your crew will arrange ground transportation from the airport/hotels with one of their trusted taxi drivers in advance)

1:00 pm - Lunch and snorkeling at Caneel Bay, St. John, USVI

3:00 pm - Relaxing sail to Maho Bay, St. John. Enjoy paddle boarding, a walk on the beach or snorkeling with the sea turtles. Watch the sunset while enjoying cocktails and hors d’ouevres and enjoy an evening of good food, games and togetherness.

Day 2

8:00 am - Breakfast, then dinghy over to Mary’s Point or Whistling Cay for a guided snorkel tour, learning about the coral reef ecosystem plus fish and coral identification

11:00 am - back to the boat for Lunch and relaxation

3:00 pm - Enjoy a leisurely sail to Waterlemon Cay, St. John. Enjoy a short hike to the Annaberg ruins for a fascinating historical tour or check out great snorkeling, world class fly fishing in the salt flats or simply relax and enjoy the calm of the afternoon.

8:00 pm - Night dive around Waterlemon Cay for any experienced and adventurous divers in the group!

Day 3

8:00 am - Breakfast followed by a nice hike/snorkel at Waterlemon Cay (depending on what was accomplished the day before) OR a quick motor sail up to Newfound Bay to try your hand at snaring a Caribbean lobster!

1:00 pm - Shoot over to Coral Bay to enjoy fresh cocktails, tasty tacos and a fun, festive atmosphere at Lime Out OR sail to Salt Pond Bay. Enjoy a quiet afternoon on a lovely white sand beach surrounded by gorgeous views. Other options include snorkeling at Booby Rock, a dive excursion, or a hike on the Rams Head Trail for an epic sunset view!

St Croix Option!

Day 4 - 5

Interested in exploring the largest island in the VI territory? St. Croix is a quiet, friendly island with a fascinating history and known for a burgeoning restaurant industry. Located approximately 35 miles south of St. Thomas and St. John, it's an exciting “beam reach” sail to and from St. Croix and therefore weather and guest dependent. With a one-way trip being approximately 4 to 5 hours of open water sailing, your crew can further discuss this itinerary option as your charter draws near plus once you're aboard and the Captain knows what the weather is doing. Once at St. Croix, enjoy world class diving on the North Shore, snorkeling with sea turtles at Buck Island, and fascinating historical relics and stories. If permissible, your crew can help rent a car and go explore the rainforest, beautiful beaches and enjoy the local culture. Fancy a round of golf? Then check out the Buccaneer for a unique island golfing experience. Plus, don’t forget to stop by the Norma’s Domino Club to enjoy local concoctions and feed the beer drinking pigs! History buff? Then tour Fort Christian, Fort Frederick, Estate Whim or the famous Cruzan Rum factory. Sail back to St. Thomas the morning of Day 6.

Day 4

8:00 am - Breakfast then enjoy an early morning hike up the Ram’s Head Trail. Return to the vessel for a relaxing, mid-morning sail to the Lovango/Congo Cay cut.

1:00 pm - Lunch. Feeling adventurous? Dive the legendary Carvel Rock, making sure to look for old cannon balls and other relics. You may even get lucky and see some local black tip reef sharks. Not a diver but still looking for an adrenaline rush? Ask your captain about some local cliff jumping options or try to surf the cut at Mingo Cay.

5:00 pm - Sunset sail to the World Famous Magens Bay, St Thomas (weather dependent) and enjoy a sunset swim, paddleboard or walk on the longest beach in St. Thomas!

Day 5

8:00 am - Breakfast followed by WATER SPORTS! Magens Bay is the perfect spot for wakeboarding, water skiing and tubing. Not into the action? Then hide out on one of the small, secluded strips of beach where you will have “the place all to yourself!”

12:00 pm - Lunch and then enjoy some time on the beach or visiting the Magens Bay Beach Bar and Boutique for some cocktails and a shopping fix. Beached out? Then try an island tour!

Day 6

8:00 am - Breakfast then motor sail up to Little St. James for a gorgeous snorkel/dive at “Ledges” or “Cow and Calf”. Enjoy lunch at the Pizza Pi boat in Christmas Cove, Great St. James (if open).

4:00 pm - Set sail for historic Buck Island off St. Thomas for a quiet evening, an ideal spot to take in the sunset, plus the opportunity to learn the history of Buck Island and its highlights.

Day 7

8:00 am - Breakfast then snorkel the wreck of the Cartanza, an old freighter with a fascinating history and/or dinghy over to Turtle Cove to swim with the turtles!

11:00 am - Downwind sail to Honeymoon Beach, Water Island. Enjoy lunch aboard and then spend the afternoon on the beach or rent golf carts and explore the island.

5:00 pm - Dinner is served and then take a leisurely sunset sail through historic downtown Charlotte Amalie and enjoy cocktails/hors d’oeuvres aboard while your crew provide a fun, historical tour of the area. Spend the night at anchor in the harbor or stay on the dock at Yacht Haven Grande (dockage at charterer’s expense). Enjoy some local nightlife or talk to your crew about throwing a fun theme party!

Day 8

8:00 am - Breakfast. Try a walking tour of historic Charlotte Amalie! Check out Emancipation Gardens, the 99 steps and the historic Fort Christian. Take advantage of duty-free shopping at vendor’s plaza or in any of the downtown boutiques.

11:00 am - Return to the boat to pack for a noon departure. Crew will arrange transportation to your hotel or the airport.

Why Choose Carefree Yacht Charters®?

Our Experience & Expertise Are Priceless

Our Experience Makes Us Unique: We're a top 5 Crewed Yacht Charter Company with over 25 years of industry experience. Our tenure includes 14 years in business as the Owners and Brokers of Carefree Yacht Charters plus 12 years as the Owners and Crew of our own highly successful yacht in the USVI, BVI, & Caribbean. When combined, we are uniquely qualified to expertly handle your vacation of a lifetime. Contact us today to get started.

Our Expertise Sets Us Apart: Our clients rely on prompt, honest and sound advice, a strict adherence to ethical and fiduciary responsibilities, an in-depth knowledge about the yachts, crews, and destinations we recommend, plus a Carefree Charter Process that results in trips of a lifetime, time and time again. Read what our clients have to say.

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Call us in our South Florida office at 954-980-9281, Toll Free at 888-670-6884, or complete our Quick Request Form. We'll match you with a charter that fits your budget, style and interests. Or, get started by viewing a sampling of our popular USVI yacht charters or our popular BVI yacht charters. .