British Virgin Islands

Plan to arrive at Tortola, BVI at least one day in advance of the sail date, usually arriving in Tortola on Friday. In both of the options, your party will have the option to stay on board the sailboat on Friday. 

 There are two ways to do this:

• Fly into Tortola Airport (EIS). This is the most direct way of arriving. A taxi will be arranged to pick up your party from the airport and get you to the Marina.
• Fly into St. Thomas, USVI (STT). It is recommended that you arrive an extra day in advance. It is recommended that you stay at the Windward Passage Hotel, directly across the street from the ferry to the BVI. It will give you an extra day to explore Charlotte Amalie, USVI. Please visit https://www.roadtownfastferry.com/ for the booking (~$103/person with a charge for luggage), select the 1:50 pm ferry to get to Tortola on time. A taxi will be provided to get you to the marina.

** Note: We can arrange for a hotel room at the Marina for those who do not wish to stay on board Friday night, at an extra charge. **

Anchors Aweigh to Cooper Island! Our adventure kicks off bright and early at 7:00 AM as we prep for our first voyage. By noon, we wave goodbye to the marina and enjoy a breezy 90-minute sail across the channel to beautiful Cooper Island.

Once we pick up our mooring ball (a secure, eco-friendly anchor point) for the night, the fun really begins. Your Captain will whisk you away to the best snorkeling spots nearby—keep your eyes peeled for the sea turtles that call this bay home! As the sun starts to dip, we’ll head ashore to the famous Cooper Island Beach Club. You can shop at the boutique, take a dip from the beach, or sample the collection at their world-class Rum Bar before sitting down to a reserved dinner.

The night is yours to finish: stay ashore for another cocktail, or head back to the boat for a peaceful evening of card games and stargazing on the water.

Our adventure continues as we set a course for the stunning North Sound of Virgin Gorda. This four-hour sail includes a refreshing lunch stop at George Dog Island, giving you plenty of time to snorkel and dip into the crystal-clear waters before we secure our evening mooring at Prickly Pear, right next to the iconic Saba Rock Resort.

Day 1: North Sound & Saba Rock: Spend your afternoon relaxing on the bar deck at Saba Rock—but keep an eye on the clock! At 5:00 PM, the famous Tarpon feeding begins, a spectacle you won't want to miss. For dinner, you have two incredible options: the restaurant at Saba Rock or the newly reimagined Bitter End Yacht Club (our top recommendation). Afterward, head back to the boat for late-night snacks, drinks, and card games.

Day 2: The Baths & Leverick Bay: The next morning, we make a short 20-minute sail to Leverick Bay to top up our fresh water and allow for any personal provisioning at the local shops. From here, the land adventure begins! We will pre-arrange a rental vehicle (available for an additional charge), and your Captain will drive you to one of the Caribbean’s great wonders: The Baths.

Before descending to the beach, we’ll stop for a panoramic view and a snack at The Top of the Baths. Then, we guide you through the massive granite boulders, tide pools, and winding water paths that make this location famous. To cap off the day, we recommend dinner at CocoMaya, a chic Asian-fusion restaurant right on the water's edge, complete with beach games and a full bar. We end the night back on board, peaceful under the stars.

Anegada: The Coral Island: Set your compass for something completely different. Unlike the volcanic peaks of the other islands, Anegada is a flat, coral atoll surrounded by one of the world's largest barrier reefs. Reaching it requires an exciting 2.5 to 3-hour sail across open water—a true sailor's passage that offers the thrill of the open sea.

Scooters, Sand, and Seafood: On shore, the vibe is laid-back and adventurous. We recommend renting scooters to zip across the island and explore the pristine, endless beaches. Browse the local souvenir shops or simply relax with a painkiller in hand.

The Main Event: Lobster Dinner: You cannot visit Anegada without tasting the island’s most famous export. For dinner, we will direct you to the finest local restaurants where the catch of the day is the legendary Anegada Lobster. Freshly caught and grilled to perfection, it is a meal—and a memory—you will savor long after the vacation ends.

Prepare for a sailor’s dream! We embark on a 3-4 hour downwind run to Little Harbour, with the wind at our backs for a smooth and impressive sail. Upon arrival, we’ll top up our fresh water and secure our mooring for a night of island fun.

Once we are settled, you can choose your own adventure on this iconic island:

• Foxy’s Tamarind Bar: Visit one of the most famous beach bars in the world. Enjoy the food, the drinks, and the music. Pro Tip: Bring a sticker from home to add to their legendary collection and leave your mark!
• White Bay Excursion: Take a scenic taxi ride over the hill to the pristine White Bay. Here, you can visit the Soggy Dollar Bar, the birthplace of the original Painkiller cocktail. If you wander over to the One Love Bar, look for Seddy—if he’s in the house, you might just get treated to an impromptu magic show that will leave you baffled.

Flexible Service:Whether you want to party until late or head back early for a quiet night, the Captain is on standby to shuttle you between the shore and the boat at your convenience. 

Our voyage concludes at the legendary Norman Island, a place steeped in maritime mystery. Local lore whispers that these very shores and the hidden caves of "The Bight" inspired Robert Louis Stevenson’s classic, Treasure Island.

A Raucous Afternoon at The Willie T: Once moored, we kick off the afternoon with a visit to the most infamous floating bar in the Caribbean: The William Thornton, known to all as "The Willie T." Arrive in your swimsuits and prepare for authentic island cuisine served with a side of pirate-themed rebellion. The Willie T is famous for its rowdy traditions, the most notorious of which is the "Rite of Passage": climbing the railing of the second deck and taking a daring plunge into the turquoise water below—often with a rebellious wink at the "Do Not Jump" signs!

The Captain’s Farewell Dinner: After drying off, we will settle in for a more refined evening ashore at the Pirates Bight Restaurant. Enjoy a delicious final dinner surrounded by the history of the cove. 

As this is our last night before returning to port, we will spend the evening packing up our treasures and preparing for a smooth return to the marina the next morning.