Sample Itinerary

Day 1

Board Yes Dear midday on Tortola, which is the capital of the British Virgin Islands. Hanrie will have lunch underway and your first cool island-inspired cocktail will be waiting. After lunch and a short chat with Christiaan about your itinerary, a relaxing sail takes you across the Sir Francis Drake Channel to Norman Island, the model for the epic novel, “Treasure Island” by Robert Louis Stevenson. At Norman Island, you’ll snorkel the Caves before heading into The Bight to watch the sunset while you enjoy sun-down cocktails and appetizers. After dinner it is off to The Willy-T a floating Bar and Schooner and one of the most legendary and infamous bars in the BVIs.

white bay jost van dyke

Day 2

After breakfast you can hike to the top of Spy Glass Hill, a known pirate lookout point. To cool off you might snorkel the Indians or Rainbow Canyons. After lunch, you’ll enjoy a short upwind sail to Peter Island, famous for the aptly named Peter Island Resort, which is a secluded retreat boasting romantic white sand beaches and unmatched island fare. Take a late afternoon stroll, meandering through the exclusive resort either stopping at the beach bar for a cool drink overlooking Dead Man’s Bay and Chest (“15 men on a dead-man’s chest, yo ho ho and a bottle of rum”) or hike the 5-mile loop which provides postcard vistas and an up close and personal look at a variety of indigenous, exotic, flowering plants overlooking Reef Bay, White Bay and Drake’s Channel. Following dinner on board, you will sip after-dinner cocktails or coffee on the trampoline watching for falling stars or maybe on the swim platform to view the tarpon show.

RMS Rhone underwater

Day 3

Today starts with a short sail to Salt Island to scuba or snorkel the RMS Rhone, one of the world’s top five wreck dives. A hike around the salt ponds of Salt Island will be in order to walk off lunch. Later you will motor around to Cooper Island for some spectacular snorkeling off Cistern point, an open reef alive with juvenile fish of endless varieties. In the afternoon, perhaps take the opportunity to explore the charming eco -friendly Cooper Island Beach Club or snorkel with the resident sea turtles. The day concludes with a short sail to a spectacular anchorage to enjoy the sunset and more of Liezl’s fantastic fare.

Day 4

Not to be missed are The Baths on Virgin Gorda. This awe-inspiring natural attraction is a collection of giant boulders which form a spectacular maze of pools and grottoes, leading to beautiful Devil’s Bay Beach. Here, Christiaan will meet you with your snorkel gear so that you may explore the boulders underwater, as well. Mooring for lunch just outside Spanish Town makes it easy to pop into the shops to purchase souvenirs or meet up with one of our preferred taxi drivers, who will take you on a guided tour of the island and the National Park. A gorgeous sail up the west coast of Virgin Gorda concludes in North Sound, where you may anchor at the Bitter End Yacht Club to enjoy the nightlife, or you may choose a quiet anchorage along Eustatia Reef, with views of Eustatia and Necker Islands. Eustatia is an extensive reef which begins at Prickly Pear Island, reaches around behind Eustatia Island passing Saba Rock and ending at Virgin Gorda’s Oil Nut Bay.

Day 5

An exhilarating morning sail up to Anegada will get the day started. Anegada, the drowned island, is nestled within the third largest barrier reef in the world. It is the only inhabited British Virgin Island formed from coral and limestone rather than being of volcanic origin. While the other islands are mountainous, Anegada is flat and low with its greatest elevation being 28 feet. This explains why for most of your 15 mile sail from Virgin Gorda the island is not visible. After lunch, head over to Cow Wreck or Loblolly Beaches to stroll the beautiful but relatively deserted north shore. Informality and relaxation are the key elements of Anegada. Deserted beaches, fringed reefs and the unique flora and fauna of the salt ponds, home to the pink flamingo, await your exploration. Lobster dinner on the beach is a unique experience. Andre will place your order early in the day as the lobsters need to be caught and prepared for grilling on the open-pit barbecues right on the beach where you dine.

Day 6

An early start from Anegada ensures plenty of time to sail back to Guana Island for snorkeling at Muskmelon Bay or Monkey Point. Following another taste-tantalizing lunch from Hanrie’s galley, you will enjoy a scenic sail along the beautiful, rugged north shore of Tortola. Tonight, you may choose to spend the evening at quiet Brewer’s Bay to enjoy a paddleboard to the beach, a hike up to the Bat Cave, or participate in some water sports. Another anchorage option would be to continue around the corner to lively Cane Garden Bay.

Bitter End Yacht Club

Day 7

A leisurely morning sail will take you to Sandy Spit or Sandy Cay for a stroll on one of the most photographed islands in the Caribbean. Next stop is White Bay, one of the BVI’s most beautiful and famous beaches. For the brave, a “Rum Shack Crawl” starts with Bushwackers at Gertrude’s, followed by Painkillers at The Soggy Dollar Bar and finishes at Ivan’s Stress Free Bar for whatever concoction you desire. By sundown, White Bay is tranquil so you may wish to make this your overnight anchorage. Alternately, it is easy to make a quick move around the corner to Great Harbour so you can enjoy the nightlife at Foxy’s Tamarind Bar.

Day 8

Early risers may wish to go for a morning stroll to experience the quiet beauty of White Bay Beach before heading back to Tortola where it all began. Time to bid Yes Dear goodbye until next time.