Destinations & Sample Itineraries
U.S. Virgin Islands: St. Thomas & St. John
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 vacation.
Day 1 - St Thomas to Maho Bay, St John
- Noon : Board your yacht in St. Thomas.
- 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, kayaking, a walk on the beach, or snorkeling with the sea turtles. Watch the sunset while enjoying cocktails and hors d’oeuvres. Enjoy your first evening of good food, games, and togetherness.
Day 2 - St. John: 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.
Day 3 - St. John: 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
Day 4 - Lovango Cay Cut to 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.
Day 5 - St. Thomas, Magens Bay
- 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.
Day 6 - Little St James, Christmas Cove to 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 in Christmas Cove, Great St. James.
- 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.
Day 7 - Buck Island, Water Island, St. Thomas: Charlotte Amalie
- 8 am : Breakfast. Snorkel, the wreck of the Cartanza, an old freighter with a fascinating history. 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 possibly at the charterer’s expense).
- Enjoy some local nightlife or talk to your crew about throwing an epic theme party!
Day 8 - St. Thomas: Charlotte Amalie
- 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 Contact Paradise Connections to Book Your Next Charter !!!
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.