I stepped onto the sailboat, the warm Caribbean breeze immediately wrapping around me like an old friend. The sun was just beginning to dip below the horizon, casting fiery streaks of orange and pink across the water. This was it, the start of an unforgettable week sailing through the British Virgin Islands (BVI) with a skipper to guide us through this island paradise. The excitement was palpable as we cast off, leaving the world behind and embracing the open sea.

The Freedom of Sailing with a Skipper

Having never captained a boat myself, hiring a skipper was the best decision we could have made. It allowed us to fully relax and soak in every moment without worrying about navigation, anchoring, or keeping an eye on the ever-changing winds. From the moment we left the harbor, the gentle sway of the boat and the sound of the waves against the hull became a soothing rhythm, setting the tone for our adventure.

Our skipper, James, was not just our guide, he was our storyteller, our local expert, and our friend by the end of the trip. He knew the best snorkeling spots, the most secluded beaches, and the liveliest bars. Every morning, as we sipped fresh coffee on deck, he would map out the day’s journey, tailoring it to our mood and the weather conditions. There was something liberating about having no fixed schedule, just the promise of new discoveries each day.

A Journey to Anegada : The Hidden Gem of the BVI

One of my favorite stops was Anegada, the outlier of the BVI, a flat coral island unlike the rest of the volcanic chain. The journey there was nothing short of magical, just open water, the scent of salt in the air, and the occasional flying fish darting alongside us. It felt like we were venturing into the unknown, far from the rest of the world.

Once we arrived, we rented scooters and zipped across the island to Loblolly Bay, where we spent the afternoon swimming in the clearest turquoise waters I’ve ever seen. The coral reefs surrounding the island are some of the healthiest in the Caribbean, making for incredible snorkeling. We floated above gardens of vibrant coral, spotting everything from parrotfish to graceful stingrays gliding along the sandy bottom. It was like being in an aquarium, except this one stretched endlessly in all directions.

That evening, we feasted on the famous Anegada lobster at a beachside restaurant, our toes buried in the soft sand as we clinked glasses of rum punch under a sky bursting with stars. There’s something truly special about eating seafood that was caught just hours before, grilled to perfection, and served with island charm. The slow pace of island life made every moment feel like a dream.

Snorkeling at The Indians and The Caves

Another highlight of our trip was snorkeling in the crystal-clear waters of The Indians and The Caves at Norman Island. The Indians, a set of rocky islets, offered an underwater wonderland teeming with marine life. Schools of shimmering fish darted around us as we glided past towering coral formations. At one point, a sea turtle lazily drifted by, completely unbothered by our presence, as if we were merely guests in its underwater kingdom.

The Caves, on the other hand, felt like an adventure straight out of a pirate movie. Swimming into the dark, cool caverns, we were met with shafts of sunlight piercing through openings in the rock, illuminating the water in an eerie yet mesmerizing glow. We half-expected to find hidden treasure stashed away inside. Legend has it that these caves were the inspiration for Robert Louis Stevenson’s Treasure Island, and as we explored their depths, it was easy to believe the stories.

Partying at Willy T’s – The Floating Bar

Of course, no BVI sailing trip would be complete without visiting the famous Willy T’s, the floating bar anchored off Norman Island. As we approached, the sounds of laughter and music carried over the water. Before we knew it, we were diving off the boat into the warm sea, then climbing up the ladder to order Painkillers and dance on the deck.

For those unfamiliar, the Painkiller is the signature cocktail of the BVI, a creamy blend of dark rum, pineapple juice, orange juice, coconut cream, and a dash of nutmeg. With a few of these in our system, we let loose, joining the eclectic mix of sailors and travelers reveling under the stars. It was the kind of carefree night that makes you feel alive, surrounded by kindred spirits who had all come to the BVI seeking adventure.

Jost Van Dyke and the Famous Soggy Dollar Bar

We also made stops at Jost Van Dyke, home to the legendary Soggy Dollar Bar. The only way to reach this famous beach bar is by swimming ashore, hence the name, as sailors often arrive with soggy bills in their pockets. We sipped their signature Painkillers while lounging in the shallow waters, the sun warming our backs and the rhythmic waves lapping at our legs.

Jost Van Dyke also had an easygoing charm that made it hard to leave. We wandered along the beach, stopping at small shacks selling handmade jewelry and local crafts, then indulged in conch fritters and fresh seafood at a nearby beachside café. The simplicity of the island, the laughter of fellow travelers, and the gentle lapping of the waves made this spot unforgettable.

Exploring Virgin Gorda and The Baths

Virgin Gorda was another breathtaking stop on our journey. The highlight here was The Baths, a stunning collection of massive granite boulders that form hidden pools and caves along the shoreline. We climbed over and through these natural formations, wading in waist-deep water as we explored tunnels carved by centuries of waves.

At one point, we found ourselves in a cathedral-like chamber where sunlight streamed through an opening above, reflecting off the water in dazzling patterns. It was one of those rare places where nature’s beauty left us completely speechless.

The Secluded Beauty of Peter Island

We also visited Peter Island, a secluded oasis with pristine beaches that felt like our own private paradise. The island’s untouched beauty was a stark contrast to some of the livelier spots we had visited. We spent the afternoon basking in the sun on Deadman’s Beach, a stretch of powdery white sand lapped by gentle turquoise waves. It was the perfect place to unwind and reflect on the journey.

Sunset at Cane Garden Bay

Cane Garden Bay on Tortola was the perfect spot to wind down. With its calm waters and palm-lined beach, it had an inviting, laid-back atmosphere. We spent our final evening here, sipping rum cocktails as the sky transformed into a masterpiece of purples, pinks, and golds. The live reggae music drifting from a nearby beach bar only added to the magic of the moment.

Unwinding in St. Thomas and Water Island

Before heading home, we spent a few days in St. Thomas to get rid of our sea legs and soak in a bit more island life. It was the perfect transition back to reality—lazy mornings by the beach, exploring Charlotte Amalie’s colorful streets, and indulging in fresh seafood with a view of the harbor.

One of the highlights was taking a quick ferry over to Water Island, a secluded gem just off St. Thomas. We spent the afternoon at Honeymoon Beach, where the soft white sand and calm waters made for a dreamy escape. With fewer crowds and a relaxed vibe, it was the ideal way to unwind after a week of adventure on the open sea.

The Magic of Sailing the BVI

Sailing the BVI with a skipper gave us the best of both worlds: adventure and relaxation. We had the freedom to explore, snorkel, and indulge in the island life without worrying about a thing. The experience was everything we had dreamed of—waking up to sunrises over the water, exploring hidden beaches, and ending each day with a new adventure.

If you’ve ever dreamed of turquoise waters, island-hopping, and sipping cocktails at a bar floating in the sea, this trip is for you. Trust me—you won’t want to come back. And even if you do, a piece of your heart will always remain in the British Virgin Islands, waiting for the next adventure.