7-Day U.S. Virgin Islands Sailing Route from St. Thomas

Located just minutes from downtown Charlotte Amalie, Yacht Haven Grande is a world-class marina that blends luxury with convenience. Whether you're docking a superyacht or stepping ashore from a sailing charter, this marina offers upscale boutiques, fine dining options, and a picturesque promenade perfect for an evening stroll. With stunning harbor views and excellent facilities, it’s not just a stopover—it’s a destination in itself.

Immerse yourself in the vibrant history of St. Thomas by wandering through the cobblestone streets of Charlotte Amalie’s historic district. Discover colonial-era architecture, charming alleyways, and cultural landmarks such as Blackbeard’s Castle and the 99 Steps. The area is also home to local shops, art galleries, and open-air markets, blending heritage with a lively island vibe. It’s a must-visit for anyone seeking a deeper connection to the Virgin Islands’ past.

Soar above the harbor aboard the Skyride to Paradise Point, a scenic tramway that lifts you 700 feet above sea level for panoramic views of St. Thomas and beyond. At the summit, you’ll find a lively deck with restaurants, cocktails, and one of the best sunset views in the Caribbean. Whether you come for the photo ops or to sip a “Bushwacker” while the sun dips into the sea, this experience adds a magical perspective to your island journey.

Set along the waterfront with panoramic marina views, Cutlass & Cane delivers a contemporary Caribbean dining experience infused with coastal charm. With its breezy, elegant atmosphere and creative takes on island flavors, this restaurant is perfect for sunset dinners or leisurely lunches. Whether you're arriving by yacht or strolling in from Yacht Haven Grande, Cutlass & Cane offers a stylish yet relaxed setting to savor the spirit of the Virgin Islands.

A hidden gem for sushi lovers, Enkai offers a fresh and refined take on Japanese cuisine in the heart of Frenchtown. With a minimalist aesthetic and laid-back vibe, the restaurant blends island energy with sushi artistry. It’s a favorite among both locals and visitors looking for high-quality seafood, creative rolls, and an intimate setting away from the tourist crowds.

Perched on the hillside overlooking the harbor, Fresh Bistro brings a farm-to-table philosophy to St. Thomas with a focus on seasonal, locally sourced ingredients. The airy terrace, welcoming service, and elegant Caribbean-European fusion cuisine create a refined yet approachable dining experience. Whether for a romantic dinner or a relaxed gathering with friends, Fresh Bistro offers the perfect balance of taste, setting, and hospitality.

Just a short sail from St. Thomas, the waters surrounding Great St. James Island are a haven for snorkelers seeking clear visibility, vibrant reefs, and abundant marine life. Christmas Cove, nestled on the island’s western side, offers calm anchorage and easy access to shallow coral gardens teeming with tropical fish, rays, and even sea turtles. Whether you're a beginner or an experienced diver, this spot is ideal for an effortless underwater escape in a serene and picturesque setting.

Anchored right in the heart of Christmas Cove, Pizza Pi offers one of the most unique dining experiences in the Virgin Islands. This vibrant floating pizzeria serves up handmade pies straight from a boat, attracting sailors, snorkelers, and day cruisers alike. Whether you're grabbing lunch after a swim or enjoying a casual sunset meal from your deck, Pizza Pi combines the laid-back spirit of island life with the comfort of a warm slice—served sea-side.

Accessible only by boat or a scenic hiking trail from Cruz Bay, Salomon Bay Beach is a secluded paradise within the Virgin Islands National Park. Framed by lush vegetation and turquoise waters, it offers a tranquil escape for those seeking soft sand, gentle surf, and excellent snorkeling. This peaceful cove is perfect for unwinding in nature, far from the crowds.

Just a short dinghy ride or trail walk from Caneel Bay, Honeymoon Beach offers a postcard-perfect stretch of white sand and calm, shallow waters ideal for swimming, paddleboarding, and sunbathing. With on-site amenities like kayak rentals, beach chairs, and a small beach bar, it strikes the perfect balance between natural beauty and casual comfort. It's a favorite among sailors looking for an easygoing beach stop with unforgettable views.

Maho Bay is a serene stretch of shoreline known for its exceptionally calm, shallow waters—ideal for beginner snorkelers, paddleboarders, and families with children. Sea turtles are frequently spotted gliding through the bay, making it a favorite among nature lovers. The peaceful beach is backed by coconut palms and offers a truly relaxing setting in the heart of Virgin Islands National Park.

Tucked into the northern edge of St. John, Francis Bay is a quiet and less crowded alternative to nearby beaches. Its long sandy shoreline and gentle waters make it a top spot for swimming and sunset strolls. The adjacent nature trail through the mangroves offers birdwatching opportunities and a deeper connection with the island’s natural beauty.

Cinnamon Bay is one of St. John’s largest and most versatile beaches, offering wide stretches of soft sand and easy access to excellent snorkeling. Surrounded by forested hills, this scenic bay is ideal for sunbathing, swimming, or simply soaking in the Caribbean views. A blend of raw nature and convenience makes Cinnamon Bay a staple on any Virgin Islands itinerary.

Overlooking Leinster Bay, the Annaberg Sugar Plantation Ruins offer a powerful glimpse into the island’s colonial past. Once a thriving 18th-century sugar estate, the site now stands as a quiet yet compelling reminder of St. John’s agricultural and cultural history. Visitors can explore the well-preserved ruins of the windmill, factory, and slave quarters while enjoying sweeping views of the bay and surrounding cays. The short hike to the site is both scenic and educational, making it a meaningful stop for history and nature lovers alike.

Tucked along the quieter northeastern shore of St. John, Newfound Bay is a hidden gem known for its rugged beauty and remote feel. Surrounded by rolling hills and untouched shoreline, it offers a raw, off-the-grid experience ideal for adventurous sailors and snorkelers. The underwater terrain features rocky ledges and coral patches where vibrant marine life thrives. Less visited than other bays, Newfound Bay invites you to embrace the untamed side of the Virgin Islands.

A Coral Bay classic, Skinny Legs captures the laid-back spirit of the Virgin Islands with its open-air setting, friendly service, and no-frills Caribbean-American cuisine. Known for its casual charm and welcoming local vibe, this dockside bar and grill is a favorite among sailors, cruisers, and island regulars. With colorful décor and a come-as-you-are attitude, it’s the perfect spot to relax after a day on the water.

Only accessible by boat or paddleboard, Lime Out is a must-visit floating taco bar that turns lunch into a tropical adventure. Moored in the turquoise waters of Coral Bay, this vibrant hotspot serves up bold flavors in an unforgettable setting. With floating stools, bar service, and views in every direction, Lime Out combines culinary creativity with island fun—perfect for hungry sailors in search of something truly unique.

Nestled along the shoreline with sweeping sea views, Miss Lucy’s offers a more serene and rustic dining experience that blends Caribbean flavors with island hospitality. With a waterfront patio shaded by sea grape trees and the sound of waves as your backdrop, this local gem is perfect for a relaxed brunch or a romantic sunset meal. It’s where good food meets quiet beauty.

Paddle through the calm, turquoise waters of Magens Bay, where kayaking offers a peaceful way to explore the shoreline at your own pace. The bay’s long stretch of golden sand invites you to slow down, relax under swaying palm trees, and embrace the quiet side of island life.

For a thrill with a view, head inland to Estate St. Peter and experience Tree Line Extreme—a zipline course that whisks you through lush treetops with panoramic views of St. Thomas and the bay. It’s an exciting way to see the island from a whole new perspective.

Tucked into the quiet shores of Water Island, Honeymoon Beach offers a peaceful escape framed by palm trees, soft sands, and gentle waves. Known for its relaxed atmosphere and family-friendly vibe, this hidden gem is perfect for swimming, lounging, or enjoying a beachside stroll. Its easy access by dinghy and clear, shallow waters make it a favorite among sailors looking for one last serene stop before returning to port.

Located just steps from the sand at Honeymoon Beach, Dinghy’s Beach Bar & Grill blends laid-back island vibes with great food, refreshing cocktails, and live music. Whether you’re grabbing a cold drink after snorkeling or settling in for a sunset meal, this open-air beach bar offers the perfect balance of flavor and atmosphere. With its welcoming energy and barefoot charm, Dinghy’s is a must-visit for anyone stopping by Druif Bay.