U.S. Virgin Islands

*7 Night Sample Itinerary

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’ve compiled a sample itinerary below to give you an idea of just how much you can accomplish within the span of a week on charter. Just remember, the nice 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. This sample includes all meals, snacks, ship’s bar, and hors d’ oeuvres unless other arrangements are made.  

Day 1

12 pm – Pickup at American Yacht Harbour dock in St. Thomas (crew will arrange transportation and provide rendezvous info)

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’ oeuvres — enjoy an evening of good food, games, and togetherness.

Day 2

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!

Day 3

8 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 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 gorgeous views. Other options include snorkeling at Booby Rock, a dive excursion, or hike Rams Head for an epic sunset view!

ALTERNATE OPTION: ST. CROIX! 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. Located approximately 35 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 exciting, 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! 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? 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

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. 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!

Day 5

8 am- Breakfast followed by WATER SPORTS! Magens Bay is the perfect spot for wakeboarding, foiling, water skiing, and tubing. Not into the action? Hide out on one of the small, secluded strips of beach where you’ll have the place to yourself!

12pm- Lunch. Enjoy some time on the beach or visiting the Magens Bay Beach Bar and Boutique for some day drinking and shopping fun. Beach’d out? Try an island tour!

Day 6

8 am- Breakfast and 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 it’s highlights.

Day 7

8 am- 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!

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 charterer’s expense). Enjoy some local nightlife or talk to your crew about throwing an epic theme party! 

Day 8

8 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 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!