First Tracks in the BVI: A Pelagic Crew Finds if Rhythm

By Betsy Chicares 

If you’ve never sailed in the British Virgin Islands, here’s your chance to experience it vicariously—complete with the lessons we learned along the way about preparation, flexibility, and the importance of the right crew. And if you have sailed there, you already know that no two trips are the same—another reason why sharing experiences within the Pelagic community continues to be so valuable.Many sailors charter catamarans in the BVI, and for good reason: interior space, low draft, and stability. In our case, however, a friend transports a privately owned Oyster 53 monohull to Tortola each season and offers it to friends for weeklong sailing adventures. It was an opportunity we couldn’t pass up.

Oyster 53 in Soper's Hole (Source: Betsy Chicares)

Selecting the right crew was the first—and arguably most important—step. From prior experience, I knew that a monohull meant less personal space than a catamaran, so compatibility mattered. We needed people with flexible personalities, a shared understanding of onboard responsibilities, thoughtful packing habits, and solid sailing skills. Fortunately, Pelagic’s network made that easy. Our club’s ethos—bringing together competent skippers and crew—proved spot on.

With the crew assembled, planning began in earnest. Since this was our first time sailing both the BVI and this particular yacht, I started compiling questions for the captain. WhatsApp quickly became our central hub for communication, enabling us to text, call, and meet virtually. Once the captain addressed our initial questions, we held a group video call to align expectations and ensure everyone felt comfortable. We later shared travel details and passport information securely through the platform.

Next came logistics. Coordinating travel to Tortola required balancing different preferences—routes through the USVI, airline choices, and arrival times. We agreed to arrive by Friday evening to ensure timely arrival and to provision together on Saturday before boarding.

Provisioning, as always, was both practical and revealing. Drawing on a prior Pelagic trip, we created a shared spreadsheet listing everyone’s “likes and yikes.” Encouragingly, the likes far outweighed the dislikes—a good omen for the week ahead. From there, we drafted a meal plan and shopping list. We brought only a few specialty items from home—Dunkin ground coffee, canned stuffed grape leaves, and vacuum-sealed smoked salmon—assuming most staples would be available locally and to avoid violating customs laws.

Getting provisions to the boat required coordination. With lots of help from the captain, we arranged transport for both our luggage and bulk items like paper goods and cleaning supplies. It paid off: when we arrived at the dock, the groundwork went smoothly and quickly.

Before departing, we had also mapped out our activities of interest. Sailing, of course, topped the list, along with snorkeling, some light exploring ashore, and time to relax. We’d all sailed together before, so we knew we functioned well as a crew. The captain’s familiarity with the yacht—having delivered it between New England and the Caribbean multiple times and in foul weather just a few months before—gave us additional confidence with the boat and its condition. Snorkel gear would be arranged locally, and we identified a few onshore highlights to round out the itinerary. The rest, we agreed, would be left to the rhythm of the trip.

We arrived in Tortola on Friday and spent the night ashore. Provisioning the next morning turned out to be surprisingly fun—especially when it came to selecting beverages. Tackling provisioning together was a pleasant difference from prior cruises in which each crew member shopped independently. Given the uncertainty of local inventory and the impracticality of bringing supplies through customs, this approach proved efficient and collaborative, and ensured everyone’s satisfaction.

At several points, we joked that the captain might balk at the sheer volume of groceries. The real test came when we began stowing everything onboard. Refrigerator space was tight, but with some strategic freezing and careful organization, everything fit. Dry goods found homes without cluttering the saloon or galley. With the boat provisioned, we settled in for our first onboard meal—and our last one on land for several days.

Our first sail, from Soper’s Hole to Peter Island, gave us a chance to get acquainted with the boat and pick up our first mooring. Despite the social media stories of difficulties with mooring balls, we had no issues at all using BoatyBall. Also, despite the recent northerly winds, conditions were calm on the leeward side of the island, and we spent the afternoon swimming and easing into the routine before preparing dinner.

Our track up the Drake Channel (Source: B. Chicares)

That evening, we checked the weather and noted the continuing, unusual northerly winds and swell lingering longer than expected. Rather than rigidly following our original itinerary, we adjusted, prioritizing anchorages with better protection. The cruising guides we brought proved invaluable as we made these real-time decisions. 

The next morning, we set off for Virgin Gorda under clear skies. Sailing up the Drake Channel was exhilarating, with crisp tacks and steady strong wind. But as we approached the island’s west coast, conditions shifted dramatically. Skies darkened, swells built, and heavy rain fell. We quickly furled the sails and motored upwind toward the shelter of Gorda Sound, joining a line of boats doing the same.

We picked up a mooring at The Bitter End and, after a damp dinghy ride ashore for a look about, we returned to the boat and settled into the familiar rhythm of cooking, sharing a meal, and socializing.

By morning, the sun had returned, but the heavy seas outside the Sound remained. With hopes of reaching Anegada, we decided to wait for better conditions. Instead, we dropped the mooring and anchored near the opening of the sound, taking the opportunity to refine our anchoring setup—including deploying the second snubber specific to the anchor rode. It was one of several valuable learning moments.

That evening, we had dinner at Leverick Bay with a former neighbor of a crew member who now lives part time on the island. The meal was excellent, though getting there and back required two spirited wet dinghy rides through choppy water—an adventure in and of itself.

We woke to find the weather had shifted in our favor and quickly set out for Anegada, mindful of the challenges posed by our 8-foot draft in its shallow approaches. Catamarans dominated the mooring field for good reason. After three attempts, the anchor held solidly in the sandy bottom and settled in.

Goats on Anegada! (Source: Betsy Chicares)

After deciding to stay an extra night, we rented a car the next day to explore the island, visiting several snorkel spots and taking in the unique landscape. While underwater visibility was limited due to recent rough sea conditions, the island offered its own rewards—including unexpected encounters with roaming goats and cows. The highlight was lunch, drinks and snorkeling at Tipsy’s, recommended by a fellow traveler. It delivered on all fronts: great food, lively atmosphere, and memorable hospitality.

Bushwacker at Tipsy's (Source: B. Chicares)

Our final stop was Jost Van Dyke. A fast, spirited sail brought us there, with the boat easily exceeding 8 knots over ground—a thrilling close to the trip’s sailing highlights. We moored near Diamond Cay, where the snorkeling proved exceptional. Clear water and abundant marine life kept us in the water for hours. Dinner at Foxy’s Taboo capped the experience, this time with calm seas and dry dinghy rides—a welcome change.As we sailed back into Soper’s Hole, it was clear our planning had paid off. We had provisioned almost perfectly, consuming nearly everything we purchased. The captain was happy to take the few remaining items off our hands—and jokingly wondered aloud, “Why is the rum gone?”

8.5 Knots of fun! (Source: Betsy Chicares)

For a first BVI experience, it was everything we could have hoped for: challenging at times, flexible by necessity, beautiful vistas, and a rewarding experience.