“You Make the Memories, We’ll Make the Arrangements”

A sailing vacation in the USVI-BVI is a holiday that is great for families, groups of friends, and couples. The following 7-Night USVI-BVI Sailing Itinerary is one sample of places to see and things to do while in the islands. Of course, we will tailor your trip according to your preferences and interests.

Xenia 74 USVI/BVI sailing itinerary
Yacht Xenia-74

Day 1 St Thomas – St John (USVI)

Meet your yacht and crew at Yacht Haven Grande Marina, St Thomas. After a brief safety meeting, you set sail for Christmas Cove near Great St James for lunch and an afternoon of snorkeling. This spot usually has lots of turtles as well as a beautiful reef that is teeming with tropical fish. In the afternoon sail to St John and anchor either behind Lovango Cay or Leinster Bay, depending on conditions. Spend your first night on your private yacht.


  • Snorkeling
  • Stand-up Paddleboarding
  • Kayaking
  • Checking out Pizza-Pi the floating pizza restaurant
USVI/BVI Sailing Itinerary 7-Night
Yacht Haven Grande Marina, St Thomas

Day 2 St John – Norman Island (BVI)

On day two, enjoy a made-to-order breakfast. Then, sail to St John. Much of this island is under the supervision of the National Park Service so it has been kept from overuse. Such a pristine environment makes a wonderful environment for the island’s many artists including painters, musicians, and writers. There are lots of hiking trails to explore, beaches to walk, and unique restaurants to try.

st John USVI
St John, USVI


  • Hike to the Annaberg Ruins.
  • Snorkel Waterlemon Cay.
  • Shop. Near Cruz Bay there’s a nice collection of shops and restaurants.

After a morning of activity, head to the BVI and clear customs. Then, sail to the Indians to snorkel and have lunch. The anchorage for the evening will be in Privateer Bay, Norman Island.

Norman Island BVI
Norman Island

This is a great place for floating, kayaking, paddle boarding, or simply enjoying the sunset. If you would like, take the dinghy into the Bight to check out the beach or bar.

Day 3 Norman Island – Cooper Island

Awake on day three to the aroma of breakfast and freshly brewed coffee. Jump in the water to swim, snorkel, or paddleboard. If you’d rather explore on land, go for a hike on Norman Island. Be sure to bring your camera because the scenery is spectacular.

yacht yes dear
Yacht YES DEAR offers scuba diving on board.

Once you’re ready, the captain will sail through Sir Francis Drake Channel up to Cooper Island. Arrive at Haulovers Bay where you can snorkel or dive. Haulovers Bay is a private anchorage where marine life flourishes! After lunch, head to the evening’s anchorage in Manchioneel Bay by Cooper Island Beach Resort.


Day 4 Cooper Island – Virgin Gorda

In the morning, leave Cooper Island and sail to Virgin Gorda. Anchor away from the crowds by the private beach of Trunk Valley Bay.

USVI-BVI Sailing Itinerary 7-Night the Baths

Then it’s just a short sail to Long Bay, Virgin Gorda for the evening’s anchorage.


  • Walk the stunning secluded beach in the morning
  • Have lunch
  • Lounge on the yacht
  • Watersports
  • Visit the Baths in the afternoon

Day 5 Virgin Gorda – Anegada

Anegada Day! Get an early start for the 1 ½ hour-sail to the island of Anegada. Anegada is markedly different from the other islands of the BVI in that it is flat, rather than mountainous. (It’s flat because it is formed from limestone and coral rather than from volcanic activity.) This idyllic island is quiet and isolated with some amazingly beautiful white sand beaches.

USVI-BVI Sailing Itinerary 7-Night Anegada Beach
Anegada Beach


  • Take a taxi to the beach. Some of the best beaches are Cow Wreck Beach, Loblolly Beach, Flash of Beauty, and Windlass Bight Beach.
  • Rent scooters or a car
  • Have a lobster dinner at The Wonky Dog or the Anegada Reef Hotel. Potter’s by the Sea serves lunch and dinner. Ask your captain to make reservations by 4 pm.
  • Visit Flamingo Pond. Here, flamingos and other sea birds have been re-established.
  • Snorkel
  • Kitesurf

Day 6 Anegada – Scrub Island

On day six of your 7-night USVI-BVI Sailing Itinerary set sail for Scrub Island. The beautiful Scrub Island Resort and Marina offers dining, a spa, shopping, a fitness center, and more. Other activities on the island include beaches, hiking, diving, and snorkeling.


  • Paddleboard
  • Kayak
  • Snorkel
  • Walk on the beach
  • Dinner at Scrub Island Resort
  • Have sundowners on the yacht

Day 7 Scrub Island – Jost van Dyke

Today’s destination is Jost Van Dyke. On the way, the first stop at Sandy Spit, a unique sandbar that is iconic in the BVI. From here you can take a leisurely hike to the Bubbly Pools. After lunch, move to White Bay.


  • Have a drink at the famous Soggy Dollar Bar
  • Visit the variety of other fun beach-bar-style establishments
  • Enjoy sunbathing on the beautiful white sand beach
  • Bubbly pools
beach time
Beach time

Choose to either sail back to St John in the evening for dinner or stay in Great Harbor on Jost Van Dyke if the group wants to go to Foxy’s for post-dinner drinks and dancing! That’s one of the joys of a yacht charter — the schedule is flexible.

Day 8 Jost van Dyke – St Thomas

After breakfast, head back to Yacht Haven Grande (about a 2-hour motor sail) in order to clear customs by 11 am. Once cleared, head back to the boat for a final toast. If you’ve enjoyed this 7-Night USVI-BVI Sailing Itinerary, check out the longer sample USVI-BVI sailing itineraries.

Contact us at 1-321-777-1707 or complete this form to discuss your vacation plans.