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Ultimate 5-Day St. Thomas Adventure with Dining Delights Itinerary

Last updated: 2024 Jun 14

Island Arrival and Historic Bites

Morning

Begin your St. Thomas journey with a delightful breakfast at Gladys' Cafe, known for its local flavors. Afterward, take a stroll through history on the Charlotte Amalie Historic Main Street Food Tour, where you'll sample the island's culinary highlights while soaking in the charming architecture and vibrant atmosphere of downtown Charlotte Amalie.

Afternoon

For lunch, head to The Twisted Cork Cafe for a casual yet gourmet experience. Post-lunch, visit the iconic Blackbeard's Castle (Skytsborg Tower) and explore the historic estate at Fort Christian, immersing yourself in the island's rich past.

Evening

As the sun sets, enjoy a sophisticated dinner with a "room with a view" at Room with a View. End your evening with a relaxed cocktail at Virgilio's Cocktail Lounge & Piano Bar, where the live music sets the perfect island ambiance.

Bedtime

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4.54
Charlotte Amalie Historic Main Street Food Tour
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4.70
Blackbeard's Castle (Skytsborg Tower)
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Snorkels, Sails, and Dolphin Tales

Morning

Fuel up for an adventurous day with breakfast at Cuzzin's Caribbean Restaurant & Bar. Then, gear up for the Saint Thomas Snorkeling, Sailing & Beach Catamaran Tour, where you'll explore the island's breathtaking underwater world and enjoy the warm Caribbean waters.

Afternoon

After the tour, grab a quick bite at Sunset Grille, known for its waterfront dining. Spend a relaxing afternoon swimming with dolphins and exploring the marine life at Saint Thomas Swim with Dolphins at Coral World Ocean Park.

Evening

For dinner, indulge in the fresh seafood at Oceana Restaurant & Wine Bar. Cap off the night with a magical Cocktail Sunset Cruise aboard Breakaway Charters at Sapphire, where you'll witness the stunning island sunset while sipping on your favorite drinks.

Bedtime

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4.50
Saint Thomas Snorkeling, Sailing & Beach Catamaran Tour
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4.72
Saint Thomas Swim with Dolphins at Coral World Ocean Park
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Kayaks, Mangroves, and Island Hopping

Morning

Start with a hearty breakfast at Mafolie Restaurant, offering panoramic views of the island. Then, embark on the St. Thomas Mangrove Kayak, Hike, & Snorkel 3-Hour Tour, where you'll paddle through the mangrove lagoons and discover the unique ecosystem of St. Thomas.

Afternoon

After working up an appetite, enjoy a casual lunch at The Greenhouse, a favorite spot for locals. Post-lunch, take the St. Thomas Island Shopping, Sightseeing, and Beach Tour to explore the island's hidden gems and enjoy some leisurely shopping.

Evening

For dinner, experience the fusion cuisine at Havana Blue, set in a tropical, open-air environment. If you're up for more adventure, consider the St. Thomas Night Kayak in the Lagoon to see the island's nocturnal marine life in a whole new light.

Bedtime

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4.74
St. Thomas Mangrove Kayak, Hike, & Snorkel 3-Hour Tour
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4.46
St. Thomas Island Shopping, Sightseeing, and Beach Tour
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Sights, Sounds, and Secret Spots

Morning

Enjoy a relaxed breakfast at Room with a View to kick off your day. Then, take in the panoramic views from Mountain Top, the highest point on the island, and visit the picturesque Phantasea Tropical Botanical Garden to immerse yourself in the island's lush flora.

Afternoon

For lunch, head to Virgilio's Cocktail Lounge & Piano Bar for a unique dining experience with live music. Spend your afternoon at the serene Water Island, a hidden gem known for its pristine beaches and tranquil atmosphere.

Evening

Dine at Mafolie Restaurant for a taste of Caribbean elegance with a side of the island's best sunset views. Conclude your day with a visit to Drake's Seat, a historic lookout offering breathtaking views of the surrounding islands under the colorful Caribbean sky.

Bedtime

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4.72
Mountain Top
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4.25
Phantasea Tropical Botanical Garden
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Final Flavors and Farewells

Morning

Savor your last breakfast on the island at Gladys' Cafe, reminiscing about the adventures you've had so far. Then, take a guided St. Thomas Private Island Tour with a Local Guide to discover any hidden spots you may have missed.

Afternoon

Enjoy a leisurely lunch at Cuzzin's Caribbean Restaurant & Bar, where the friendly staff will bid you farewell with a taste of true island hospitality. Spend your final afternoon at Coki Beach, known for its vibrant marine life and excellent snorkeling opportunities.

Evening

As the sun sets on your St. Thomas journey, dine at The Twisted Cork Cafe for a casual yet memorable meal. Reflect on your trip over a final drink at Gladys' Cafe, where the laid-back atmosphere is the perfect setting to say goodbye to the island.

Bedtime

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