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Ultimate 7-Day St. Thomas Adventure for a Sailing Enthusiast Itinerary

Last updated: 2024 Jun 14

Sailing into Paradise

Morning

Start your day with a delightful breakfast at Gladys' Cafe, known for its local flavors. Afterward, head to Yacht Haven Grande for your first sailing lesson with a local instructor, immersing yourselves in the art of sailing in the Caribbean waters.

Afternoon

For lunch, savor the seafood at Oceana Restaurant & Bistro, offering a perfect oceanfront dining experience. Post lunch, continue your sailing lesson, practicing different techniques and enjoying the sea breeze.

Evening

Conclude your day with a romantic dinner at Room with a View, a fine dining restaurant with panoramic views of the Charlotte Amalie Harbor.

Bedtime

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5.00
Yacht Haven Grande
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Historic Charms and Culinary Delights

Morning

Enjoy a delicious breakfast at The Twisted Cork Cafe, a cozy spot with a variety of options. Embark on a historical journey with a visit to Blackbeard's Castle (Skytsborg Tower) and Fort Christian, immersing yourselves in the island's past.

Afternoon

For lunch, indulge in a unique dining experience at The Galleon Restaurant, set in a historic Danish warehouse. Afterward, explore the vibrant 99 Steps and the charming streets of Skytsborg Historical Park.

Evening

Dive into the local food scene with a "Flavors of St. Thomas" food tour, experiencing the diverse culinary offerings of the island.

Bedtime

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4.70
Blackbeard's Castle (Skytsborg Tower)
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4.57
Fort Christian
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Beach Bliss and Water Adventures

Morning

Start your day with a refreshing breakfast at The Smoking Rooster, known for its island-inspired dishes. Spend the morning relaxing at the world-famous Magens Bay, soaking up the sun and swimming in the crystal-clear waters.

Afternoon

For a unique experience, try the Saint Thomas Coral World Ocean Park Ticket, where you can explore the marine life and even swim with dolphins. Afterward, enjoy a beachfront lunch at Sunset Grille.

Evening

Conclude your day with a romantic sunset cruise aboard Breakaway Charters at Sapphire, sipping cocktails and enjoying the breathtaking views of the Caribbean Sea.

Bedtime

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4.67
Magens Bay
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4.44
Saint Thomas Coral World Ocean Park Ticket
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Island Exploration and Local Cuisine

Morning

Enjoy a leisurely breakfast at Greengos Caribbean Cantina, known for its authentic Caribbean flavors. Embark on a St. Thomas Private Island Tour with a Local Guide, discovering the hidden gems of the island.

Afternoon

Stop for a traditional island lunch at Cuzzin's Caribbean Restaurant & Bar, a local favorite. Continue your exploration with a visit to Phantasea Tropical Botanical Garden, immersing yourselves in the lush tropical beauty.

Evening

For dinner, head to Havana Blue, a trendy restaurant offering a fusion of Caribbean and Latin cuisine, accompanied by live music.

Bedtime

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4.20
St. Thomas Private Island Tour with a Local Guide
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4.25
Phantasea Tropical Botanical Garden
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Adventure and Adrenaline

Morning

Start your day with a hearty breakfast at Mafolie Restaurant, known for its stunning views. Embark on a thrilling Saint Thomas Shark Encounter at Coral World Ocean Park, getting up close with these magnificent creatures.

Afternoon

After the adrenaline rush, enjoy a relaxed lunch at Pie Whole, a charming spot with a variety of sweet and savory pies. Spend the afternoon at Skyride to Paradise Point, taking in panoramic views of the island.

Evening

For dinner, try the innovative dishes at Virgilio's Cocktail Lounge & Piano Bar, known for its creative cocktails and live music.

Bedtime

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4.20
Saint Thomas Shark Encounter at Coral World Ocean Park
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Skyride to Paradise Point
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Nature's Beauty and Culinary Delights

Morning

Enjoy a leisurely breakfast at The Galleon Restaurant, savoring the flavors of the island. Explore the natural beauty of St. John with a St John Guided Tour with Annaberg Plantation Visit, including a visit to the pristine Trunk Bay Beach.

Afternoon

For lunch, have a picnic on the beach with a gourmet meal from Sunset Grille. Afterward, take a dip in the turquoise waters and relax on the white sandy beach.

Evening

Head back to St. Thomas and enjoy a romantic dinner at Room with a View, overlooking the sparkling lights of the harbor.

Bedtime

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4.60
St John Guided Tour with Annaberg Plantation Visit
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Farewell to Paradise

Morning

On your last day, savor a special breakfast at Pesce Italian St. Thomas USVI, known for its authentic Italian cuisine. Spend the morning at Coral World Ocean Park, exploring the underwater world with activities like SNUBA and the Sea Trek.

Afternoon

Enjoy a farewell lunch at Greengos Caribbean Cantina, reminiscing about your adventures in the Caribbean. Take a relaxing stroll through the Phantasea Tropical Botanical Garden, taking in the sights and sounds of the tropical paradise.

Evening

Conclude your trip with a romantic dinner at Oceana Restaurant & Bistro, savoring the flavors of the sea and toasting to your unforgettable Caribbean vacation.

Bedtime

Find amazing hotels in St. Thomas, US Virgin Islands.