Cruising the Virgin Islands is an exhilarating experience and with a seasoned Captain onboard, you can relax and enjoy the sound of the soft winds brushing the sails. Spend your days calling each island home – from St. Thomas to Tortola and all the treasures in between. Our crews are happy to help you map out a trip all your own with a custom BVI sailing itinerary. The key to enjoying life on island time is to not be too ambitious. If an island is calling your name, stay the day and enjoy on island sightseeing, biking through the mountains or hiking to see the views of the islands from above. We promise they do not disappoint.
We know you can’t wait to set sail. This page is designed to provide you with some ideas to help you customize your own adventure. These destinations and descriptions are presented to you based upon our own personal recommendations and we welcome you to steal this page verbatim and consider your trip planned!
USVI / BVI sailing itinerary – departure from St. Thomas, USVI
Board your charter and let the fiesta begin! Set sail or motor to St. John, a jade-hued island consisting of 11,000 acres of preserved National Park and some 5,000 inhabitants. Dock at Cruz Bay, a popular tourist destination on St. John which has many shops and cafes ranging from small smoothie and food vendors to high-end jewelry and craft gift stores. Cruz Bay is a hub for visitors and boasts Wharfside Village as well as Mongoose Junction – both offering everything from souvenir knick knacks, luxury handicrafts and jewelry boutiques. There are also plenty of watering holes and in the evenings Cruz Bay can transform into a lively little destination. Mongoose Junction is a premier shopping destination in the Virgin Islands. The buildings and streets have a storied history – as they were designed and inspired by Danish plantations and built using local coral, brick and stone. Or you may opt to spend the day at Trunk Bay Beach – the most photographed beach in the U.S. Virgin Islands and home to underwater trails that make for fantastic snorkeling for beginners. The beach has a snack bar, changing room and showers if you plan to venture onto the island for shopping after a swim. For dinner, your onboard private chef will prepare a gourmet meal to be enjoyed open-air style on the boat or for a fine dining experience on land head to ZoZo’s at the Sugar Mill. Sitting atop the ruins of an 18th-century sugar mill overlooking the private Cruz Bay, ZoZo’s meshes fine Italian with Caribbean flare such as it’s Wild Boar Cacciatore or Fettuccine Carbonara featuring Caribbean lobster. Enjoy a nightcap under the stars or a movie in the main salon.
Breakfast and mimosas to start Day 2 off right! A morning cruise over to Waterlemon Cay in Leinster Bay, St. John for excellent snorkeling or hop on the dinghy and go ashore for hiking or a self-guided tour of the historic Annaberg sugar mill plantation ruins dating back to 1718. The view from the ruins overlooks the bay and certainly doesn’t disappoint – it’s a great family photo opportunity. Return to the boat for lunch and proceed to West End (locally known as Soper’s Hole), Tortola to clear British Virgin Islands Customs and Immigration. Here you can snag any provisions you may have forgotten (toothbrush or some shades) and check out the colorful shops before we head to The Bight, a former private hideaway, at Norman Island to moor for the night. Since you’ll be arriving later in the day, we’ll likely find mooring near the William Thornton, better known as the Willie T, a floating barge that serves as a restaurant and bar. Watch for cannonball dives off the sterncastle and feel free to take the dinghy to climb aboard and join the fun. Be warned that local island spirits can result in varying levels of patron disrobement and festivities can continue late into the night. Nightcap onboard as the sound of a Caribbean party carries across the cay.
Just outside The Bight is Treasure Point – a most intriguing destination in the Virgin Islands. As the story goes, in 1750 a Spanish galleon headed home for Spain was severely damaged then raided by a mob of drunk Englishmen. The treasure was skippered by Owen Lloyd, a competent sailor familiar with the Virgin Islands. He unloaded the valuable cargo at The Bight and the manifest read: 55 chests of silver dollars, 3 large chests of plate and wrought silver and 200 pounds of cochineal (a dried Mexican insect that produces a red dye). In total, a fortune amounting to $200,000 (today several millions). After burying the chests, Owen Lloyd and all but three crewmen sailed to St. Thomas. The three guards left behind were discovered burying treasure. As word spread of the buried silver, citizens of the islands descended upon Norman Island to claim the fortune. Only $20,000 worth of the treasure was found – the most recent finding in 1910, a chest of coins discovered in the southern caves at Treasure Point. To explore The Caves, dinghy over early in the morning with snorkeling gear so you can swim and snorkel the three caves and surrounding reefs. Keep an eye out for Sergeant-major fish (look for yellow and black stripes). They won’t be hard to spot as they have become accustomed to being fed by snorkelers. If you’re on the hunt for buried treasure, venture into the northern cave as it goes back into the island some 70 feet and the water is only about chest deep. Bring a flashlight and check out the colored veins in the walls. After lunch, depart Norman Island for Cooper Island – some 7 nautical miles away. Cooper Island is one of the five small islands covering a distance of 10 miles forming the southern boundary of Sir Francis Drake Channel. With a full service dive shop offering full dive training, this is a must visit destination for scuba divers planning to rive the famous RMS RHONE, a British mail steamer that was holed and sunk during a hurricane in 1867. The Cooper Island Beach Club also features a restaurant, bar and gift shop.
“Yo ho ho and a bottle of rum, 15 men on dead man’s chest”. This famous ditty stems from the history of Peter’s Island where Blackbeard marooned 15 men on Dead Chest Island – off the east coast of Peter’s Island -with just a bottle of rum. But who needs rum when Deadman Bay boasts one of the most beautiful beaches in the Caribbean. Also ashore is a beach bar and grill operated by Peter Island Resort, whose owner also controls most of the island property as well. While Peter Island Resort is a luxury upscale establishment, the bar and grill at Deadman Bay are laidback and welcoming to daytime yachtsmen.
Another island receiving its name from Mr. Columbus – Anegada is just a short, offshore passage from Tortola. The only island made of coral, Anegada boasts the 3rd largest barrier reef in the world – Horseshoe Reef. The extensive reefs once made cruising around the island a treacherous game. Some 300 or more ships are known to have wrecked as they ran their hulls into the sharp coral. With today’s GPS technology though, charterers are able to expertly navigate around the reefs. Enjoy a day of snorkeling and keep a careful eye for plunders of Spanish galleons as well as large fish including conch and lobster.
Passage to Virgin Gorda in the morning. The Fat Virgin, or Virgin Gorda was named by Christopher Columbus himself as he described the island to resemble a reclining pregnant woman. A most diverse cruising destination, attractions include The Baths – six story boulders rising from the sea making naturally blue glittered grottoes. Anchor at Savannah Bay for an afternoon secluded on a powder white sand beach, then head to the Gorda Sound for an evening of solitude and a chance to try out some onboard water toys, pull out a board game, float in the water, or enjoy a good book and cold beverage. Make way to Spanish Town and the Virgin Gorda Yacht Harbour where you can go ashore and enjoy the boutiques, supermarket, ice cream parlour, art & jewelry, BVI apparel, bank and bars. If you need to connect to WiFi you can visit the chandlery for free internet access. There is also fishing tackle supplies here along with a ships’ store for any bareboaters needing charts, ropes, fasteners or other necessities.
Get an early start with breakfast in the salon as you head to Jost Van Dyke’s Manchioneel Bay. Anchor off the southwest shore of Little Jost at Foxy’s Taboo. For those seeking a little exercise, venture on a short hike from Foxy’s Taboo to the Bubbly Pool, a natural whirlpool created by the tide pushing bubbling water into the small crevice that meets the 5-foot deep pool. This small, lush, mountainous retreat also has a disproportionately amount of classic Caribbean beach bars and restaurants – helping Jost earn its “party island” reputation. We recommend Foxy’s Tamarind Bar in Great Harbour. Owned by Foxy Callwood, a famous seventh-generation Van Dyker and local calypsonian, Foxy’s hosts live music Thursdays, Fridays and Saturdays. You may even be lucky enough to be serenaded by Foxy himself. Soggy Dollar Bar in White Bay is another popular beach bar destination featuring its signature Painkiller cocktail. Be warned, there is no dock at Soggy Dollar so be prepared to wade ashore for drinks and pay with your “soggy dollars”.
Sail back to Red Hook for check-in and afternoon flights home (or the beginning of your extended stay on St. Thomas).