Travels with Hannah: Another Point of View from Tortola

I had left my house in the blackest hours. It was below freezing north of Boston, hovering around 20 degrees on an early January morning, when I slipped out in the velvet night, well before 5 a.m. To reach my boat in Tortola, the largest island in the British Virgin Islands, a volcanic archipelago offering up natural beauty, incomparable snorkeling, and a legendary drink known as “The Painkiller,” I would have to fly through the U.S. Virgin Islands first, landing in St. Thomas, shuttling across from Cyril E. King Airport toward the eastern end of the island, where ferries depart daily from Red Hook.

In the moody, late-afternoon light, my party of five arrived, via water taxi, to a cove, home to a marina of boats owned by The Moorings. Launched in 1969 by a navy veteran named Charlie Cary, The Moorings began as a way for sea lovers to take to the waters themselves; experienced travelers could explore the Caribbean islands through bare-boat charters, sailing through the crystalline waters on their own. The business began with a handful of boats, but has since expanded to include over 400 of them, spread across 20 international cruising destinations. Guests can also opt to charter a fully staffed boat, with a captain, stew, and on-board chef.

Our boat, the Andromeda, was a crewed 5800 Master, a six-cabin catamaran, ideal for up to 10 guests. The master suite was mine, a spacious room with a long bathroom with dual sinks and an enclosed shower. Two additional cabins below deck also enjoyed en suite bathrooms and showers. On the main deck, two smaller rooms had the ultimate amenity: a sunken shared outdoor space that looked out onto the bow of the yacht, ideal for coffee at sunrise or cocktails at sunset.

We set sail the next morning, first for the Indians, a snorkeling destination that is among my favorites. A bit of a swell had turned the others off, so it was only a crew member and me in the water, swimming through a thick sea, in the presence of a five-foot barracuda on one of the rock formation’s outer reefs. Later, we anchored at Cooper Island, lounging at the beach club, an eco-resort that was fully renovated in 2018, a year after Hurricanes Irma and Maria brought damage and devastation to both the U.S. and British Virgin Islands.

Sailing through the Caribbean is a privilege untold. I’ve taken double-digit trips down to this particular band of islands, but from the vantage point of the water, the perspective is new. I was able to swim from the boat, first thing in the morning, straight into Devil’s Bay National Park, with a waterproof bag strapped across my back. From there, I scrabbled through the Baths, still quiet so early in the morning — late in the day, it might as well be Walt Disney World — boulders forming still turquoise caves in the middle of a perfect beach.

Even if you arrive by boat, there’s plenty of stops to make on land. For our charter, that included a sundowner at Saba Rock, an island of a hotel that originally opened in the 1960s and that closed for a hurricane-related restoration (it reopened in the fall of 2021). At 5 p.m. each day, the hotel schedules a tarpon feeding off its main dock, and guests can watch the staff feed the hulking, massive, floating cannibals. The playful upstairs bar is also home to a pool table and some of the most incredible views of the British Virgin Islands available from anywhere on the islands.

After Saba Rock, we caught a boat to the Bitter End Yacht Club, which opened in 1969 and is currently in a state of expansion — the property reopened in 2022 post-hurricanes and has added two over-water villas to its resort — for dinner.

But the next day on the water was, for me, the most exciting. We were headed for an island I’d never visited: Anegada, the most far-flung of the British Virgin Islands, a low-lying coral island known for its succulent and sweet Caribbean lobster. It would take a few hours to sail there, and so we bounced and lobbed in on the flybridge, or on the netting of the Andromeda’s bow — where beanbag chairs were fastened, for our unique comfort.

Anegada is a sleepy island, with roaming cows and a car rental system that is more like a system of borrowing. As the designated driver of a pickup truck with bench seats affixed to the flatbread, I hoped for the best, reminded myself to stay to the left, and strapped in.

There wasn’t much to worry about, as it turns out. We didn’t encounter much oncoming traffic on our way to Cow Wreck Beach, nor did we see a single traffic light. A bit of weather blowing in — our only day of rain all week — kept us off the beach. But it hardly ruined the day. By evening, we were outside again, this time at the Lobster Trap, a captivating restaurant right at the water’s edge serving just-plucked Anegada lobster, grilled in the shell and shellacked with butter.

We had to sail back toward Tortola the following day, but not before we made the de rigueur stop at the Soggy Dollar, on Jost Van Dyke’s White Bay. The bar is where The Painkiller — a drink that blends dark rum, orange juice, pineapple juice, cream of coconut, and a shave of fresh Grenadan nutmeg — was invented, but the true thing to order is the Coco Lima, a refreshing blend of coconut rum, lime juice, cream of coconut, and club soda.

I took a final swim on our last morning, to the bleating of goats from a nearby island. With my snorkel and mask on, I dipped around the boat, searching for one last showing. I was greeted by a spray of fish. No turtles this time. I read it as a sign: I would just have to come back. Leaving an island is always hard, of course, particularly in January. But leaving all of them, all at once? Practically impossible.