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Your Caribbean Adventure Starts Here

Sample Itineraries Aboard Kerry Lee.

Explore the Virgin Islands or St. Maarten at Your Own Pace.

Sample 7-Day Itinerary

Day 1

Depart Tortola - Norman Island (snorkeling caves + beach bar)

Day 2

Peter Island - Cooper Island Beach Club

Day 3

The Baths on Virgin Gorda

Day 4

Anegada (lobster dinners + secluded beaches)

Day 5

White Bay on Jost Van Dyke (Soggy Dollar Bar)

Day 6

Sandy Cay and snorkeling adventures

Day 7

Leisurely return to Tortola

Britt's Favorite
7-Day BVI
Sailing Itinerary

Aboard Kerry Lee | Lagoon 46 | Sleeps 6 | Fully Crewed

Imagine waking up to turquoise waters, fresh tropical fruit, and the quiet hum of a yacht slicing through paradise. Aboard Kerry Lee, every day is curated for connection, indulgence, and pure escape.

This is a sample itinerary to spark your travel daydreams. Every charter is fully customized to match your pace, preferences, and sense of adventure.

Day 1: Welcome Aboard

Your week begins with a warm welcome at the marina. Step onto the Kerry Lee and settle into your private stateroom with a welcome drink in hand. As the sun sets, enjoy your first dinner on board, crafted by your private chef, and toast to the days ahead.

This evening is all about settling into the rhythm of yacht life. Watch the sky turn pink from the flybridge, feel the ocean breeze, and start to unplug. Whether you’re celebrating a special occasion or simply celebrating life, this is your first taste of effortless luxury at sea.

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Day 2: The Bitter End and Saba Rock

We set sail to Virgin Gorda's famed North Sound. Spend your day exploring the boutique charm of the Bitter End, kayaking along the coast, or sunbathing on deck. That evening, head ashore for cocktails and dinner at the iconic Saba Rock.

This part of the Virgin Islands feels like a playground for the stylish and sea-loving. Enjoy paddleboarding in the calm turquoise bay, browse waterfront shops, or sip a handcrafted cocktail as dinghies glide by. The night wraps with island music and views that remind you just how far away real life feels.

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Day 3: The Baths and Coco Maya

After breakfast, cruise to The Baths, a natural wonder made of granite boulders, sea pools, and hidden caves. Swim, hike, or simply take it all in. In the evening, enjoy a beachfront dinner at CocoMaya, one of the most stylish restaurants in the Virgin Islands.

Wade through shallow pools tucked between towering rocks, then hike up for a panoramic view of the Caribbean. It’s one of the most photographed places in the BVI for good reason. After a sun-soaked day, CocoMaya delivers a romantic setting with glowing lanterns, oceanfront fire pits, and dishes that fuse Asian and Latin flavors with fresh island ingredients.

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Day 4: Norman Island and Willy T’s

Today is made for snorkeling and stories. Begin your day at The Indians, one of the most colorful reef spots in the islands. Then grab a drink at Willy T’s, the legendary floating bar. Both lunch and dinner are served on board by your private chef.

Norman Island is said to have inspired "Treasure Island" — and it’s easy to see why. Swim through hidden caves, chase schools of tropical fish, and float without a care in the world. If you're feeling social, Willy T’s is the spot to let loose. Or stay aboard and enjoy a peaceful sunset dinner with a wine pairing tailored to your taste.

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Day 5: Anegada and Lobster Under the Stars

Sail to the flat and peaceful island of Anegada. Visit Conch Island, walk secluded beaches, and keep an eye out for flamingos. End the day with a fresh lobster dinner and stargazing from the deck.

Anegada feels like your own private island, with wide-open skies, powder-soft beaches, and a slower pace. You can rent a scooter to explore, find secret swimming spots, or do absolutely nothing at all. In the evening, your chef prepares freshly caught Anegada lobster served al fresco on deck under a canopy of stars.

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Day 6: Jost Van Dyke and Soggy Dollar

Your final full day takes you to Jost Van Dyke, home of the famous Painkiller cocktail. Relax at the Soggy Dollar Bar, visit Ivan’s Stress-Free Bar, and soak up the island spirit. Lunch is served on board. Dinner can be enjoyed either on the yacht or ashore.

The vibe here is classic Caribbean — sandy feet, reggae music, and smiles from everyone you meet. Swim ashore to the Soggy Dollar (where the name comes from exactly that), sip rum cocktails, and browse the local beach shops. Whether you party a little or relax a lot, Jost Van Dyke is the perfect send-off.

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Day 7: Farewell Sail

Ease into your final morning with a calm and scenic sail back to the marina. It’s the perfect way to close out your week in paradise.

Spend these last few hours soaking up the view, sipping coffee on the flybridge, or reliving your favorite moments from the trip. This isn’t just the end of a vacation, it’s the beginning of your obsession with yacht life. We’ll be here when you’re ready to come back.

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Alternative Destinations:

U.S. Virgin Islands (St. Thomas, St. John, Water Island)

St. Maarten, Anguilla, and St. Barth’s

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Love snorkeling? Prefer secluded beaches? Into local island culture? We’ll craft the itinerary to your preferences.

Ready to Design Your Dream Charter?

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