Sail, Sip & Unwind: A Week Aboard a Catamaran in the British Virgin Islands

Arrive in Tortola and step aboard your fully provisioned catamaran, where everything is ready to start your week. After a brief safety orientation, you’ll sail away from the marina and into the sparkling blue waters of the BVIs.

Settle into your private cabin—each with its own bathroom—while your group eases into island time with wine, cocktails, and a charcuterie spread on deck. Your first short sail brings you to a cove off Peter Island, where you’ll spend the evening enjoying a simple dinner prepared onboard and your very first sunset at sea. Fall asleep to the gentle rocking of the boat and the quiet calm of the Caribbean night.

Wake to sunshine and calm water as your first full day in the islands begins. Mornings aboard are wonderfully slow: coffee on the top deck, warm ocean breezes, and nowhere you need to be. Cruise to Norman Island and spend the afternoon enjoying the lively atmosphere at the legendary Willie T’s floating bar. Music, cocktails, and a fun crowd make this a classic BVI experience. Adventurous travelers can join the tradition of jumping from the upper deck into the sea before returning to the comfort of your catamaran for a relaxed evening on the water.

Today you sail to breathtaking White Bay on Jost Van Dyke—one of the most stunning beaches in the Caribbean. The water here truly looks unreal: crystal-clear shades of turquoise and blue stretching in every direction.

Swim ashore to the iconic Soggy Dollar Bar, birthplace of the famous Painkiller cocktail, and spend the day soaking in the laid-back beach atmosphere. Lounge chairs, soft white sand, calm waters, and a lively but relaxed vibe make this one of those places you never want to leave.

Enjoy an unhurried morning in White Bay with plenty of time to swim, float, paddleboard, or simply relax onboard. For an extra touch of relaxation, book a massage at the floating spa and fully embrace the slower pace of island life.

Later, head ashore for cocktails at Ivan’s Stress Free Bar—perfectly named for the mood of the entire trip. In the evening, take a short cruise to Great Harbor and enjoy dinner at the beloved Foxy’s, known for its barefoot charm, live music, and easygoing Caribbean atmosphere.

Today brings one of the longer sailing days of the trip. With the sails up and the engines off, you’ll glide quietly across the water toward Saba Rock. It’s during these stretches of sailing that the true magic of a catamaran trip sets in—uninterrupted views, ocean breezes, and nowhere to rush.
After lunch onboard, tender over to Prickly Pear Island to explore quiet beaches and enjoy a secluded afternoon in the island. As evening approaches, head to stylish Saba Rock for sunset drinks before continuing to Oil Nut Bay for dinner at Nova, where elevated dining and panoramic views create an unforgettable evening.

Start the morning with breakfast at the iconic Bitter End Yacht Club, just a quick tender ride from your mooring. The rest of the day is intentionally relaxed—lounge on the boat, swim in the calm waters, revisit the beach, or spend the afternoon at Oil Nut Bay’s beautiful infinity pool and overwater hammocks. This is the kind of day that makes you completely lose track of time in the best possible way.

Cruise to the southern end of Virgin Gorda for a visit to The Baths, one of the BVIs’ most famous natural wonders. Wander through giant granite boulders, hidden grottos, sunlit caves, and shallow turquoise pools that feel almost surreal.

On the return sail, stop to snorkel over the historic wreck near Salt Island before enjoying your final evening in the islands. Choose a casual dinner onboard or head ashore to Cooper Island for excellent food, island cocktails, and a visit to their renowned rum bar.

Savor one final quiet morning on deck with coffee, ocean views, and the gentle sounds of the marina coming back into view. Cruise back to Tortola feeling rested, refreshed, and already dreaming about returning to the British Virgin Islands.