Sailing the British Virgin Islands (BVI): A 7-Day Itinerary

Your adventure begins with a relaxed morning of getting familiar with your boat, completing check-out, and provisioning for the week ahead. Once you’re stocked and settled, set sail toward Norman Island for a fun and easy first day on the water. Drop anchor near the famous Willy T’s, a floating bar and restaurant with a laid-back, pirate-ship vibe that sets the tone for the week.

Grab a casual lunch and a cold drink while you soak up the island energy. Then, if you’re feeling brave, join the tradition and jump off the back of the boat into the turquoise water below. It’s a rite of passage for BVI sailors and a perfect way to kick off your trip.

Insider tip: Get to Willy T’s a bit early for a relaxed atmosphere before the afternoon crowd arrives. If you want to swim or snorkel, the nearby The Bight offers great visibility and calm waters for an easy first dip.

Sail over to Cooper Island, a serene and eco-friendly gem known for its laid-back charm and stunning views. Once you’ve moored, spend the afternoon exploring the beach or snorkeling just off-shore before heading to The Rum Bar for a tasting flight from their impressive collection of over 300 rums from around the world. The staff love to share their favorites, so don’t be shy about asking for recommendations.

As the sun sets, enjoy what many call the best land-based dinner in the BVI at the Cooper Island Beach Club. Every dish is thoughtfully prepared, and the relaxed open-air setting makes it even better. Whatever you do, save room for dessert, as their sweets are truly unforgettable and the perfect ending to a perfect day.

Insider tip: Make dinner reservations in advance, especially during peak season, and plan to arrive early for cocktails with a view. The sunsets here are some of the best in the islands.

Start your day with a sail to The Baths on Virgin Gorda, one of the most iconic spots in the BVI. Swim to shore and wander through the massive granite boulders, hidden pools, and sea caves that make this place so magical. If you prefer a smoother start, you can sail directly to Leverick Bay, pick up a mooring ball, and take a quick taxi ride to The Baths instead.

After exploring, head back to Leverick Bay to relax and enjoy the view from your mooring. In the evening, check out their lively events. On some nights you can catch the family-friendly Pirate “Happy Arrrr” Show, or if you’re there on a Friday, don’t miss the Beach BBQ, complete with music and dancing under the stars.

Insider tip: Visit The Baths early in the morning before the crowds arrive, and bring water shoes for climbing through the rock formations comfortably.

Enjoy a relaxed morning sail over to The Bitter End Yacht Club, a beloved destination for sailors and divers alike. This area offers some of the best underwater scenery in the BVI, and Mountain Point is a standout dive site with vibrant coral, colorful fish, and calm conditions perfect for all experience levels.

After your dive, spend the afternoon exploring the marina village or lounging by the water with a drink in hand. As the day winds down, head to nearby Saba Rock for happy hour or dinner. The views are stunning, the atmosphere is lively, and the cocktails are top-notch.

Insider tip: Book your dive in advance, as slots can fill up quickly. Arrive at Saba Rock before sunset to snag a prime table and watch the sky light up over North Sound.

Today is all about enjoying the sail to Jost Van Dyke, one of the most iconic islands in the BVI. The journey itself is part of the adventure, offering beautiful open-water views and the chance to relax under full sail. Once you arrive, pick up a mooring ball (this is a great day to use Boaty Ball), hop in your dinghy, and head over to White Bay.

Swim ashore to the legendary Soggy Dollar Bar, where the Painkiller cocktail was born. Sip one (or two), play a round of beach games, and soak up the easygoing island vibe that makes Jost so special.

Insider tip: Bring some cash in a waterproof pouch for Soggy Dollar, since it earned its name from soggy bills paid by swimmers coming ashore. Arrive before midday if you prefer a more relaxed scene before the afternoon crowd.

Sail over to Cane Garden Bay, a lively spot on Tortola known for its calm waters, crescent-shaped beach, and local charm. Once you’re settled, take a stroll to Callwood Distillery, one of the oldest continuously operating rum distilleries in the Caribbean. The rustic setting and traditional production methods make it a fascinating stop, and the tasting is a must for rum lovers.

As evening approaches, enjoy a leisurely dinner at Myett’s, where you can dine with your toes in the sand and listen to live music as the sun sets. The beachside atmosphere, friendly service, and fresh seafood make it a perfect way to unwind after a day on the water.

Insider tip: Try to visit Callwood Distillery earlier in the day, as it sometimes closes mid-afternoon. Stay ashore after dinner to enjoy the music and the local nightlife scene.

On your final day, sail back to the marina to return your boat, taking in the last views of the sparkling BVI waters along the way. Once your sailing adventure concludes, hop on a ferry or private water taxi to St. Thomas.

Check in to the Secret Harbour Beach Resort for a relaxing stay. Enjoy the calm beach, clear waters, and easy access to local dining and activities. It’s the perfect way to unwind, reflect on your week of sailing, and soak in the last bit of Caribbean sun before heading home.

Insider tip: Plan your ferry in advance to ensure a smooth connection, and consider a late afternoon check-in so you can catch the sunset from the resort beach.