Paradise Connections Yacht Charters Sample Crewed Yacht Charter Itinerary for US Virgin Islands (USVI)

Destinations & Sample Itineraries

U.S. Virgin Islands: St. Thomas, St. John & St Croix

Map of US Virgin Islands (USVI)

The United States Virgin Islands – America's Paradise
Come and enjoy yourselves.

This sample itinerary will give you an idea of how much you can enjoy your charter vacation without leaving US waters. The crew are always happy to discuss and change the route depending on weather and, of course, your suggestions.

The all-inclusive charter week offers you a private Captain and Chef (additional crew on larger yachts), guest cabins with ensuite bathrooms, all meals and beverages aboard including ship’s bar, appetizers, cruising permits and mooring ball fees. All meals enjoyed ashore will be at your expense.

Day 1

After your arrival at the St. Thomas International Airport (STT), take a taxi to meet your crewed charter yacht where it is docked or anchored. Your crew will advise on transportation and arrival information. You may board your yacht at noon and, in Caribbean style, cold local-specialty cocktails will be served. From American Yacht Harbor in Red Hook, you can motor or sail to Cinnamon Bay on St.John for lunch onboard. Snorkel the nearby reefs and then take a leisurable sail to Maho Bay, St. John where you can enjoy watching the turtles come up for air, walk on the beach or paddle board around the bay which is very protected for your night anchorage. This is also where we have enjoyed memorable sunsets while sipping on a cold beverage and hors d’oeuvres. Just a good way to unwind after traveling to paradise.

Day 2

Enjoy a pleasant breakfast, then dinghy over to Mary’s Point or Whistling Cay for a guided snorkel tour, learning about the coral reef ecosystem and fish/coral identification. Return to the yacht for a lovely lunch onboard and a swim. Enjoy a short sail up the channel to Watermelon Cay, St John. There is a nice shoreside trail to the Annaberg Ruins where you will enjoy a historical tour of the sugar plantation and slavery. You can also choose a shorter walk up to Murphy’s Mansion with amazing views over the bay. Nearby the mooring field you will have an opportunity to kayak, paddle board and snorkel or dive around the Cay and for the fishermen, there are salt flats for bone-fishing or fly-fishing. Another calm anchorage for stargazing.

Day 3

Breakfast followed by a nice hike/snorkel at Waterlemon Cay or motor sail up to Newfound Bay for some fishing and lobster hunting. Continue on to Coral Bay to enjoy some time walking around this quaint town or the swim up festive “Lime Out” floating bar or sail to Salt Pond Bay. Enjoy a quiet afternoon on a gorgeous white sand beach surrounded by gorgeous views. Other options include snorkeling at Booby Rock, a Scuba dive or take a hike on Ram Head Trail for an Epic sunset view with St. Croix in the distance.

Day 4

After a hearty breakfast, Enjoy a downwind sail to Lameshur Bay for a lunch stop and water sports. In the afternoon sail to Cruz Bay on the Western side of St. John. Your crew will moor the yacht near the harbor and take the tender in to explore this very colorful town and meet the friendly locals at Mongoose Junction. Stop in for a cold one at the street-side Woody’s bar with a World famous happy hour. The yacht will find a calm anchorage near Caneel Bay for the night where you can enjoy another perfect sunset over St. Thomas.

Day 5

Breakfast followed by lots of water-sports after a beam reach sail to Magens Bay. Weather permitting this is the perfect spot for wakeboarding, paddle-boarding, water skiing and tubing. Not up to the water fun? Chill out on the beach where you can find secluded sections of beach all to yourself or stop at the Beach Bar and Boutique for shopping and enjoying local cocktails.

Days 4 & 5 - Alternate itinerary: St Croix

Interested in exploring the largest island in the VI territory? St. Croix is a quiet, friendly island with a fascinating history and a burgeoning restaurant industry. St Croix is located approximately 35 miles south of St. Thomas and St. John. It is an exciting beam reach sail to and from St. Croix, with the one-way trip being 4-5 hours of compelling, open water sailing.

Once arrived in St Croix, you’ll enjoy world-class diving on the North Shore, snorkeling with sea turtles at Buck Island, and fascinating historical relics and stories.

Perhaps you'd like to rent a car and explore the rainforest, beautiful beaches and enjoy the local culture.

Fancy a round of golf? Check out the Buccaneer for a unique island golfing experience.

History buff? Tour Fort Christian, Fort Frederick, Estate Whim, or the famous Cruzan Rum factory.

Sail back to St. Thomas the morning of Day 6.

Day 6

Motor or sail over to Great St. James where you can tuck in to Christmas Cove. Here is some of the best snorkeling where spotted eagle rays and turtles are in abundance. Close to shore is a shallow ledge where a large variety of smaller schools of colorful fish hide. This anchorage is part of the Parks division and mooring balls are free. Not too far West lays “Cow and Calf” which is perfect for Scuba diving near the anchorage. Set Sail for historic Buck Island on St. Thomas and enjoy a quiet evening, enjoying the sunset and the pretty scene.

Day 7

After breakfast, 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. Head off on a 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. At sunset it is nice to slowly motor through the cuts through historic downtown Charlotte Amalie and enjoy cocktails and hors d’oeuvres while your crew anchors in the harbor or dock at Yacht Haven Grande (dockage possibly at charterer’s expense). Enjoy some local nightlife or enjoy an Epic theme party.

Day 8

After breakfast you have the chance to see more of the 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 and if you are carrying your purchases, a taxi will be on standby to return you to the dock. Now it is time to pack and say farewell to your crew until you return for the next unforgettable trip on an epic yacht charter. Your crew will arrange transport to the airport or accommodations if you decide to stay in paradise a little longer.

Remember, there are many variations to this sample itinerary. Your charter will be customized to fulfill the dreams of your charter party. That's the beauty of a Virgin Islands crewed charter yacht sailing vacation.

If you want to scuba dive, there are boats that specialize in this activity. They will be well-equipped and have a divemaster or dive instructor aboard and will make sure you dive on some spectacular spots. Another possibility is to do a "rendezvous" dive. This is where a yacht will coordinate with shore-based dive operators to take you on a dive.

Or maybe you want to spend more time sailing than at anchor and improve your sailing skills at the same time. Your experienced captain will be happy to oblige your wishes.

Whether you want an active nightlife visiting local hot spots or just enjoy the pleasure of quiet, secluded anchorages, a charter yacht in the Virgin Islands can accommodate your desires.

And, of course, if your idea of the ideal vacation is no itinerary at all, then a crewed yacht charter vacation is the perfect choice. You can decide each morning over coffee in the cockpit what you want to do that day (even if it's nothing at all), and it's OK to change your mind, too!

Our professional crews will make sure each charter guest experiences the perfect personalized itinerary for their Virgin Islands sailing vacation.

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