USVI Charter Yacht Itinerary is starting to look like it may be possible before the British Virgin Islands opens. There are still many questions to be answered for this to happen. For those wondering what a possible itinerary may look like through the USVI, I give you Charter Caribe’s sample Below.


“Not sure of what to expect on your first crewed charter in the USVI? This trip is “all about you!”, since you can do as much or as little as you’d like. We have compiled a sample itinerary below to give you an idea of just how much you can accomplish within a week on charter. Just remember, the beautiful thing about this type of vacation is that there is no set itinerary, and it’s all up to you! The crew will always be happy to provide suggestions based on your group’s interests or, quite simply, “how you’re feeling that day.”

Let's have some fresh lobster on your USVI Charter yacht Itinerary
Let’s have some fresh Lobster!

Day 1 USVI Charter Yacht Itinerary St Thomas to Maho Bay St John

Noon Pickup at American Yacht Harbour dock in St. Thomas (crew will arrange transportation and provide meeting information)
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’oeuvre and enjoy an evening of good food, games, and togetherness.

USVI Charter Yacht Itinerary
Cocktail Hour on your Charter Yacht

Day 2 USVI Charter Yacht Itinerary Whistling Cay, Waterlemon Cay

8 am 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 ID.
11 am Back to the boat for Lunch and relaxation
3 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 pm Night dive around Waterlemon Cay!

USVI Charter Yacht Itinerary
USVI Charter Yacht Itinerary taking in Annaberg Sugar Plantation

Day 3- Waterlemon Cay, Coral Bay, Rams Head

8 am Breakfast followed by a nice hike/snorkel at Waterlemon Cay (depending on what you accomplished the day before) OR a quick motor sail up to Newfound Bay to try your hand at snaring a Caribbean lobster!
1 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 gorgeous white sand beach surrounded by magnificent views. Other options include snorkeling at Booby Rock, a dive excursion or hike Rams Head for an epic sunset view!

Turtles and Yachts OH MY! USVI Charter Yacht Itinerary

Option for including St Croix in your USVI Charter Yacht Itinerary

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 a burgeoning restaurant industry.
St Croix, located approximately Thirty-five miles south of St. Thomas and St. John; it’s 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 STX, you’ll enjoy world-class diving on the North Shore, snorkeling with sea turtles at Buck Island, and fascinating historical relics and stories!

Cannons for poles on Hassel Island USVI
Cannons for poles on Hassel Island USVI

If permissible, your crew can help 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.
Don’t forget to stop by the Norma’s Domino Club to enjoy local concoctions and feed the beer drinking pigs!
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 4 Lovango Cay Cut, Magens Bay St Thomas

8 am Breakfast. 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 pm Lunch. Are you feeling adventurous? Dive the legendary Carvel Rock, making sure to look for old cannonballs and other relics. You may even get lucky and see some local blacktip 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 pm Sunset sail to the World Famous Magens Bay, St Thomas (weather dependent) and enjoy a sunset swim, paddle or walk on the longest beach in St. Thomas!

USVI Charter Yacht Itinerary
Snorkel around Watermelon Cay off St John USVI

Day 5 Magens Bay water sports

8 am Breakfast followed by WATER SPORTS! Magens Bay is the perfect spot for wakeboarding, foiling, water skiing, and tubing. Not into the action? Hideout on one of the small, secluded strips of the beach where you’ll have “the place to yourself!”
Noon Lunch Enjoy some time on the beach or visiting the Magens Bay Beach Bar and Boutique for some day drinking and shopping fun.

Beached out? Try an island tour!

Water Skiing on your USVI Charter Yacht Itinerary

Day 6 Little St James, Christmas Cove, Buck Island

8 am Breakfast Motor sail up to Little St. James for a gorgeous snorkel/dive at “Ledges” or “Calf and Cow.” Enjoy lunch at Pizza Pi, in Christmas Cove, Great St. James (if open).
4 pm Set Sail for historic Buck Island (STT) and enjoy a quiet evening, enjoying the sunset and learning the history of Buck Island and the highlights.

Cocktail hour off of Caneel Bay on St John USVI

Day 7 Buck Island, Water Island, Charlotte Amalie

8 am Breakfast Snorkel, the wreck of the Cartanza, an old freighter with a fascinating history! And dinghy over to Turtle Cove to swim with the turtles!
11 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 pm Dinner Take a leisurely sunset sail through historic downtown Charlotte Amalie and enjoy cocktails/hors d’oeuvres while your crew provides 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 the charterer’s expense).
Enjoy some local nightlife or talk to your crew about throwing an epic theme party!

Snorkeling and finding Sea Urchins- USVI Charter Yacht Itinerary

Day 8 Charlotte Amalie USVI Charter Yacht Itinerary

8 am Breakfast. Try a walking tour of historic Charlotte Amalie! Check out Emancipation Gardens, the 99 steps, and the landmark Fort Christian.
Take advantage of duty-free shopping at the vendor’s plaza or in any of the downtown boutiques.
11 am Return to the boat to pack for a noon departure. The crew will arrange transportation to your hotel or the airport.
12:01 pm Book your next charter!

USVI Charter Yacht Itinerary

Thank you to Charter Caribe for allowing us to use their marketing materials. Our link takes you to the yachts in this fleet that we are happy to suggest


Check out our Blog Entry on St Thomas Vacation All Inclusive Yacht Charters

Visit Hassle Island, USVI, for the best Caribbean History that we have seen!

Take a St John Yacht Charter

Charter Yacht Grace

Charter Yacht Twin Flame


Select your yacht for your USVI Charter yacht Itinerary


Looking for more USVI Charter Yacht options? No problem! Use our yacht search to find more and fine tune your perfect Caribbean vacation.

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