Set Sail | Explore the Relaxation and Beauty of the U.S. and British Virgin Islands

I came to the Virgin Islands a year ago to charter a catamaran with a group of new friends. Having never been to these islands, much less done a private charter experience, I had no expectations other than to catch a glimpse of sea turtles and make uninterrupted progress on the book I was reading. The experience blew me away, as did the camaraderie that forms when living on a boat with relative strangers, the quirky characters you meet at far-flung beach bars, and the boundless natural beauty of the Caribbean. But what I loved most about this trip was that every day was a new adventure. With no rigid itinerary, our only concern was keeping the boat running, finding fresh seafood and choosing which idyllic cove to drop anchor in next.

Photo courtesy of Scrub Island Resort, Spa & Marina

It’s my second time chartering a boat through the U.S. and British Virgin Islands. We began our trip by flying into Charlotte Amalie on St. Thomas and grabbed a cab to the Frenchtown marina, only five minutes from the airport. After checking in with the charter company, we walked along the dock to find our vessel, a spacious Fountaine Pajot Saona 47, which served as our vehicle and hotel for the next 10 days. I’m thankful that this sailing catamaran comfortably housed our crew of eight, with each couple getting their own bedroom and bathroom. 

While we began our boat trip on St. Thomas, we planned to spend most of our time on several other islands along both the U.S. and British sides of the chain, where beaches and bays would be less crowded by hotel and cruise ship guests. Our first night was spent at the dock in Charlotte Amalie before sailing on to Maho Bay on St. John, our last stop on the U.S. side before continuing to the British Virgin Islands.

Photo courtesy of Scrub Island Resort, Spa & Marina

Once in the British Virgin Islands, Sky, my partner and the vessel’s captain, and I spent the afternoon at Scrub Island Resort, Spa & Marina, a sandy-white four-star hotel that spans an entire private island. We dinghied into the marina, our modest vessel dwarfed by the other guests’ catamarans and yachts. We explored the island via golf cart, following winding roads up hills to see tucked-away villas, the pristine sands of North Beach and the garden that provides fresh ingredients for the resort’s on-site restaurant, Cardamom & Co. 

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But for us, it was the launch point to access Anegada, a sandy strip of land only 11 kilometers from Virgin Gorda. Our reasons for pushing onward were plentiful; for me, I was searching for the famous Anegada lobsters, and for Sky, it was the thrill of sailing on the open Caribbean Sea. 

The next day, we set off for Anegada bright and early. Our confidence was high as we looked to the horizon to see near-perfect sailing weather. Strong winds, relatively small swells and sunshine would make this trip a breeze. 

Photo courtesy of the British Virgin Island Tourist Board

We dingied over to Potter’s by the Sea, a beachside bar where NFL jerseys and gimmicky t-shirts swayed from ceiling rafters and pillars covered in decades-old graffiti from past patrons. 

After a pre-dinner cocktail and beach walk, our little crew set off for our reservation at The Lobster Trap. We called ahead with our orders so the restaurant could go out to their traps and get us fresh lobster for our dishes. Seated on the dock-like patio, we split conch fritters, rice and beans, and perfectly blackened lobsters dipped in butter. The following day, we sailed back to Virgin Gorda to Spanishtown.

Photo courtesy of Scrub Island Resort, Spa & Marina

Our days on the catamaran almost blur together in their effortless, scenic perfection. Each morning on the boat, I poured a cup of coffee and sat atop the catamaran, the only time I could get away with skipping sunscreen needed to protect me from the blazing Caribbean sun that shines later in the day. 

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I watched the crews of the other catamarans and sailboats relax with their books and coffee or busy themselves hanging up towels and swimsuits. We lounged, read, and swam for the rest of the day as we hung out at the beach. Sky sat atop the boat when we sailed, scanning for reefs and rocks. We all took turns keeping him company, and he entertained us with stories about local pirate history and the illustrious owners of yachts passing by. 

Photo courtesy of Scrub Island Resort, Spa & Marina

On Norman Island, we stretched out on beach chairs with plates of conch fritters from Pirates Bight, snorkeled through sea caves, and capped off the day by leaping from the top deck of Willy T’s into the crystal waters —a floating bar and grill that gives “dive bar” a whole new meaning.

We stayed the night docked at Salt Pond Bay on the southeast end of St. John. With moorings for only two boats, it’s an incredibly private and tranquil place to snorkel. All afternoon and the following day, I swam above reef ravines, teeming with swaying anemones and fish in brilliant shades of blue and yellow, all unphased by the occasional swimmer who joined them.

Photo courtesy of Scrub Island Resort, Spa & Marina

On our last night before returning to Charlotte Amalie, we moored in Christmas Cove, where we stumbled upon an impromptu rave and ordered wood-fired pizzas from Pizza Pi, a takeout-only restaurant on a boat. As the sun dipped below the horizon, we sat on the front of the ship, star-gazed, listened to music, and savored our last night in paradise. The beauty of a sailing trip through the Virgin Islands isn’t just in the stunning beaches, the fresh seafood, or even the thrill of navigating between the islands—it’s in the freedom to explore at your own pace, the camaraderie built over days on the water and the sense of adventure that lingers long after you’ve returned to shore.