Travel | Sail the British Virgin Islands

Sail the British Virgin Islands

By Robert E. Haywood



In the beginning, God created the British Virgin Islands for sailors. Or, at least, it would seem so. With more than fifty islands making up this archipelago with perfect temperatures and dependable trade winds, you can sail from island to island and experience the different textures of each tropical haven. Because there are so many islands, you can always see land—if this matters to you—and find the lee side of an island when foul weather approaches.

To sail these waters, you need great skill in handling a large boat and many years of experience with all the intricacies of sailing, including boat safety. A thorough understanding of navigation, changing weather conditions, and winds is paramount. As we learned, a squall can sneak up, and then you find yourself navigating a storm. 

We are fortunate in Annapolis because you can learn these skills with a series of classes at one of the excellent local sailing schools and then master them with repeated practice on the Bay. Instead of managing all the facets of sailing yourself, you can hire a captain and even a chef, and many people do. However, we only wanted to bareboat charter, which means that we sailed and provisioned the boat ourselves. 

We chose a 46-foot Lagoon Catamaran through Horizon Yacht Charters in Tortola, one of the companies recommended to us by several Annapolitans who have sailed the BVIs numerous times. At this date, these charters range from $1,000 to over $3,000 a day, depending on the size and style of your boat, and much more if you add a captain, a chef, and a hired crew. Obviously, this is a pricy getaway, but cruising these Caribbean-blue waters is thrilling and unforgettable for those who love to sail. Several other charter companies are also good, so do the research to find the best boat and rate for you.

One nice thing about Horizon is that it is located at the Nanny Cay Resort and Marina in Tortola. This marina has a grocery store underneath its office, so you can provision your boat right before boarding.

At the outset of our 8-day voyage, we had big plans to cook dinner on the boat most nights. However, after a 3 to 4-hour sail and some snorkeling, once we found and secured a mooring ball, we were ready to relax. It was tempting and easy in the late afternoon to hop on our dinghy to visit each island’s colorful bars and restaurants.

This is one of the best parts about sailing the BVIs: the chance to experience the local culture and cuisine of many different islands in a relatively short span of time. Also, there are many services just for boaters. For example, at Jost Van Dyke, we were greeted very early in the morning by a local on his skiff and purchased fresh empanadas cooked that morning by his aunt. At other harbors, which become like small floating villages, the locals who pull alongside in their boats have ice for sale and offer to dispose of your trash for a small fee. These are the small, time-saving luxuries a sailor learns to appreciate.

For our 46-foot catamaran, we needed a crew. There were six of us, with Kymberly Taylor serving as our captain. Although we met regulars who sail large yachts with as few as two or three crew members, we welcomed all these hands on board so that we could alternate tasks. In addition to a captain, at the very least, you need a strong and stable person to hook the mooring ball to secure your boat overnight. There is now an app where you can reserve a mooring ball in advance, and it is a good idea to do so. Depending on the season, the mooring balls can be in short supply.

Because Annapolis and the Eastern Shore are nautical towns, many people in the area have sailed the BVIs. Most of the islands are uninhabited, but there are plenty of inhabited islands to visit, and everyone seems to have their favorite. In 2017, Hurricane Irma, a brutal Category 5 storm, caused enormous damage, but the BVIs have come a long way in rebuilding the infrastructure. 

Our charter company suggested a personal itinerary for us—one that suited our time frame and travel plans. Much information is available online, so take some time and enjoy the process of planning your own visit to this sailor’s paradise. Here are just a few of our favorite spots:



Norman Island

Norman Island is just under three miles long and only accessible by boat. Many claim it was this island that inspired Robert Louis Stevenson’s novel, Treasure Island. The island is currently owned by Henry Jarecki, an academic, businessman, and scion of a shipping family, but boaters are still allowed to visit. For lunch or dinner, visit the local restaurant Pirate’s Bight, which serves typical island food like jambalaya, snapper, and swordfish.

In the evening, ride your dinghy (or even swim) to the infamous floating pirate ship restaurant and bar, Willy T. Join the fun by jumping off the ship’s roof into the water below. The party can get loud at night, so if you are a light sleeper, you will not want to moor your boat too close to Willy T’s.

The Indians

North of Norman Island, you can spend a half day snorkeling at “The Indians,” a collection of 60-foot rock formations that resemble an Indian headdress. Here, you will discover superb scenery and some fabulous snorkeling or diving.

Virgin Gorda

Virgin Gorda, the third-largest island (Tortola is the largest), is known for its baths consisting of gigantic granite boulders and half-submerged rocks on the southern shore of the island. Here, you can swim, snorkel, and explore these primeval grottos and tunnels at your leisure. On the northern mountainous side, you can hike and enjoy a panoramic view of the surrounding islands.

Jost Van Dyke

Although Jost Van Dyke is one of BVI’s smallest islands, it has great local Caribbean charm and casual beach dining. We enjoyed Foxy’s Taboo, which has been around since 1968, and the modest Gertrude’s Beach Bar and Grill. The menu is alos typical to almost all the islands: Jerk Chicken, Conch Fritters, Mahi-Mahi with Creole Sauce, and Spiny Lobster.


These spots are only the beginning; we could have easily visited a different island every day over our 8-day adventure. It’s cliché to call a Caribbean adventure “paradise,” but on a sunny day or a rainy afternoon with a double rainbow spanning the horizon, it is places like the BVIs that give the word a modern meaning.


Official Website:   |   BVI Mooring App:   |   Nanny Cay Resort and Marina:   |   Tortola:



© Annapolis Home Magazine
Vol. 14, No. 6 2023