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Ultimate 5-Day Island Adventure in St. Thomas, US Virgin Islands Itinerary

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day 1

Island Welcome and Historical Delights

St. Thomas Itinerary - February 28

Morning. Begin your journey with a delightful breakfast at The Greenhouse Restaurant & Bar, offering a serene ambiance and a menu filled with local flavors. After breakfast, immerse yourself in the island's history with a visit to the iconic Blackbeard's Castle (Skytsborg Tower). Explore the historic tower and the surrounding grounds, learning about the island's pirate past.
Afternoon. For lunch, head to Duffy's Love Shack, a vibrant spot known for its eclectic menu and island-inspired cocktails. Post-lunch, take a leisurely drive to the majestic Drake's Seat, where you'll be treated to panoramic views of the surrounding islands and azure waters. Capture the beauty and serenity of the Caribbean.
Evening. As the sun sets, enjoy a relaxed dinner at Tickles Dockside Pub, a local favorite with a laid-back atmosphere and fresh seafood. Afterward, take a stroll through the historic district and witness the charming architecture. Conclude your evening with a visit to 99 Steps, a hidden gem with a story to tell.
day 2

Beach Bliss and Tropical Gardens

St. Thomas Itinerary - February 29

Morning. Start your day with a delicious breakfast at Snow White Bar n Grill, offering a variety of morning favorites. After breakfast, head to the renowned Magens Bay, consistently ranked as one of the world's most beautiful beaches. Spend the morning relaxing on the pristine sands and swimming in the crystal-clear waters.
Afternoon. For lunch, enjoy the casual beach vibes at Sapphire Beach Bar, located right on the stunning Sapphire Beach. Indulge in Caribbean specialties and refreshing drinks. Post-lunch, visit the tranquil Phantasea Tropical Botanical Garden, where you can wander among exotic plants and colorful blooms.
Evening. Dine at The Rum Hut, a beachfront restaurant offering a relaxed atmosphere and a menu filled with island-inspired dishes. After dinner, take a short drive to Skytsborg Historical Park to witness the remnants of an old Danish fort and enjoy the cool evening breeze with a view of the harbor.
day 3

Island Hopping and Scenic Views

St. Thomas Itinerary - March 1

Morning. Enjoy breakfast with a view at Sunset Cove Poolside Bar & Grill, located at a resort with stunning ocean panoramas. After breakfast, catch a ferry to nearby Water Island and spend the morning at the serene Honeymoon Beach. Relax on the soft sands or snorkel in the calm, clear waters.
Afternoon. Return to St. Thomas for lunch at Iggies Beach Bar & Grill, a lively spot with a diverse menu and a beachfront setting. Post-lunch, take a scenic drive to the famous Mountain Top, the highest point on the island. Enjoy a world-famous banana daiquiri and take in the breathtaking views of Magens Bay and the British Virgin Islands.
Evening. Indulge in a fine dining experience at The Tap & Still Redhook, known for its upscale ambiance and delectable cuisine. After dinner, take a ride on the Skyride to Paradise Point and witness the island's twinkling lights from above. Savor a nightcap at the top while enjoying live music and the cool Caribbean breeze.
day 4

Hidden Gems and Cultural Treasures

St. Thomas Itinerary - March 2

Morning. Start your day with breakfast at Bernie's Bar & Grill, a local spot with a welcoming atmosphere. After breakfast, visit the lesser-known Vessup Bay, a quiet and picturesque beach where you can enjoy the morning sun and the sound of gentle waves.
Afternoon. For lunch, head to Cruzan Beach Club, a beachside establishment with a diverse menu and a relaxed vibe. After a satisfying meal, explore the historic Fort Christian, the oldest standing structure in the U.S. Virgin Islands. Learn about the island's colonial past and the role it played in the region's history.
Evening. Dine at Shoreline Bar & Grill, offering a blend of international and local dishes in a casual, open-air setting. After dinner, take a leisurely walk through the Yacht Haven Grande, admiring the luxury yachts and the vibrant atmosphere of the marina. End the evening with a drink at one of the waterfront bars.
day 5

Nature's Bounty and Farewell to Paradise

St. Thomas Itinerary - March 3

Morning. Enjoy a final breakfast at Petite Pump Room Bar & Restaurant St. Thomas, known for its morning specialties and friendly service. After breakfast, take a guided kayak tour through the serene Mangrove Lagoon. Paddle through the mangroves, spot marine life, and learn about the importance of this unique ecosystem.
Afternoon. For your last lunch on the island, visit RooT 42 Bar And Grill, a hidden gem with a menu that highlights local ingredients. After lunch, spend your final afternoon at Secret Harbour Beach Resort, where you can snorkel, sunbathe, or simply reflect on the memories you've made during your time in St. Thomas.
Evening. As the sun sets on your last day, enjoy a memorable dinner at Exclusive Bar Lounge & Restaurant, a sophisticated spot with a menu that combines global flavors with local flair. After dinner, take a moment to appreciate the beauty of the island at night, perhaps with a quiet walk on the beach or a final toast to the Caribbean sunset.
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