Sample 7-night itinerary for the Virgin Islands

The Caribbean Virgin Islands, including the US and British Virgin Islands, are known as a sailor’s paradise for their many clustered islands with protected bays, clear waters, colorful reefs, water sports and fun beach bars. The following is a sample 7 night cruising itinerary to give you some idea of the possibilities available for your crewed yacht charter vacation. Your group may plan a different itinerary than this sample itinerary and your crew will be able to make many suggestions that will show you the best vacation depending on your group’s interests.

Day 1

Swimming in the Caribbean

Welcome! After meeting your crew they will help you aboard and let you settle into your cabins. Once you have a tropical cocktail in hand the crew will give a brief safety briefing and show you around your private charter yacht. Now is a great time to discuss plans for the week or put final touches on a planned itinerary taking into account the direction of the breeze. Then it's time to hoist the sails and head to your first Caribbean beach or bay so you can dive into the warm, clear water!

If you are meeting your yacht in St Thomas, USVI

Set sail to St John which is home to a large National Park that covers much of the island both above and below water and is home to tropical and migrating birds, fish, corals and other marine life. Dive into the waters at picturesque Trunk Bay and then head over to Francis Bay, St John for dinner, drinks and your first evening aboard in the Virgin Islands.

The following morning you will clear out of US customs in St Thomas and sail over to Tortola and clear into the British Virgin Islands. You can pick up the rest of the itinerary from here and subtract one of the BVI anchorages.

If you are meeting your yacht in Tortola, BVI.

Sail the short reach to exclusive Peter Island. Here you will anchor in the pristine water at Deadman's Bay and take your first swim in the turquoise waters of the Caribbean Sea. After a delicious lunch aboard it's time to set sail to Salt Island and snorkel (or scuba dive) the Wreck of the Rhone, famous for its part in the movie, 'The Deep', then on to Cooper Island for dinner and your first night aboard under the starry Caribbean sky.

Virgin Gorda beaches

Day 2

After a swim or paddleboard and a nourishing breakfast it is time to raise the anchor and head to one of the most recognized place in the BVI's is The Baths, a unique formation of large boulders, set along the beach of the southern tip of Virgin Gorda. You can explore the many sandy rock caverns either by foot or by snorkel – or relax aboard with a cocktail, a good novel and your favorite tunes. In the afternoon we will sail to The North Sound, the BVI's watersports playground. The protected waters in The North Sound lend themselves to water activities including windsurfing, water-skiing, kayaking, a game of volleyball on the beach, or take the opportunity to see some of the Virgin Islands flora and hike up to Gorda Peak, the highest point on Virgin Gorda.

After all the action you will be ready for appetizers and sundowners back aboard the yacht while the sun sets. followed by a hearty dinner.

Sail to Anegada

Day 3

Following breakfast, take part in an adventurous sail to Anegada, a flat coral atoll in the north west corner of the BVIs which is completely surrounded by a reef. In long years past large ships have been lost on the reef, providing an underwater paradise for scuba divers and snorkelers alike. A trip to Loblolly Bay for some unforgettable snorkeling is a must. Anegada is surrounded by a mile of the most glorious white sand beaches and is also renowned for the best grilled lobster in the Caribbean. Lunch will be served on board. Famous for its local lobster, Anegada is the perfect place to enjoy dinner ashore.

Necker Island British Virgin Islands

Day 4

After breakfast aboard, haul up the anchor, raise the spinnaker and sail downwind for Monkey Bay, Guana Island. Get involved in the sailing or lay out and watch the world sail by. After snorkeling and lunch, sail along the north shore of Tortola to Cane Garden Bay, a palm lined beach with a lively Caribbean feel. Cocktail hour back on your yacht, while the sun sets over the islands ends another perfect day, followed by good food and good company.

Day 5

Soggy Dollar Bar, Jost Van Dyke

Reaching north again set sails for Jost Van Dyke, the beach bar capital of the islands. Drop the anchor at Sandy Cay for lunch and kayak ashore to explore the island. Then its off to White Bay on Jost Van Dyke, home to the legendary white sandy beach and the Soggy Dollar Bar or to Great Harbour, home of the world famous Foxy's, where you are often entertained by Foxy himself. Or head to one of Jost Van Dyke’s very secluded anchorages and watch as pelicans dive for their supper and just relax under Caribbean stars and warm evening breezes.

Dinner aboard a crewed yacht charter

Day 6

After a relaxed morning coffee and breakfast, up anchor and raise the sails to head around Tortola’s West End where you can make stop at Soper’s Hole which has souvenir and gift shops in a picturesque setting. Then an invigorating sail upwind to Norman Island of piracy fame, for a lunch stop at The Caves. The Caves are a Marine National Park which provides stunning snorkeling and the adventurous can swim into the caves where pirates of old stashed their booty! As the sun starts to dip we can either head into The Bight for some lively nightlife at the famous floating bar The Willy T, or to the seclusion of beautiful Benures Bay for a last idyllic evening in the BVIs.

Day 7

The Indians, British Virgin Islands

The Indians are a short sail from Norman Island and offer an excellent deep water scuba dive or cliff snorkel. The Indians are large rock pillars rising from the sea bed that abound with a rich variety of fish, sponges and corals. Float along with shoals of Sergeant Majors and Creole Wrasse as they feed on rich plankton blooms.

Depending on where you’re departing the yacht, set sail to your final evening anchorage which is close to your end port. Time to have a celebratory evening meal, cocktails and reminiscing about your fun and adventurous week spent sailing the Caribbean Virgin Islands.

Day 8

After a breakfast and a swim it is time to take stock of the great week you’ve had with family and friends, take some last group photos, say your goodbyes and make plans to return as your crew guides the yacht you to your departure port by noon for your onward journey.

Itinerary disclaimer: Some places on this itinerary can be inaccessible due to closure, time constraints with your charter or weather.

Customized itinerary

Your itinerary is flexible and can involve as much or little sailing as you’d like. This is what one of our guest’s final itinerary looked like:

Sailing itinerary for the Virgin Islands

Virgin Island Videos

Guest video aboard catamaran Miss Kirsty
Virgin Islands flyover with catamaran Whisper

Why choose Sailing Directions for your Virgin Islands Yacht Charter Vacation?

"Sailing Directions itself did everything I could ever ask. We were matched with a perfect vessel and the support from the booking through the cruise was thorough and professional. Thank you again for everything!"

Sailing Directions is dedicated to crewed yacht charters in the Caribbean with most of our focus and expertise in the Virgin Islands. We know the yachts and crews well, we book a high volume of charters and which allows us to get you the best terms on the best boats. Sailing Directions is a top 5 charter brokerage for the Virgin Islands crewed yacht fleet and we have been in business for over 10 years with great customer reviews. Learn more about our charter brokerage company and the value we offer you as our customer.

Group aboard Crewed Catamaran

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