Exploring the Virgin Islands: Top 5 Must-See Islands, Activities, and Sailing Options
- Brandi Thompson
- Jun 30
- 4 min read
The Virgin Islands offer a unique blend of natural beauty, rich culture, and exciting adventures. What makes this destination even more fascinating is that the Virgin Islands are split between two territories: the United States Virgin Islands (USVI) and the British Virgin Islands (BVI). Each side has its own charm, history, and attractions. For travelers eager to explore both, chartering a sailboat is a fantastic way to experience the islands up close, hopping from one to another at your own pace. This guide highlights the top five islands you should visit, what to do there, where to stay, and how sailing between the islands works, including the difference between sailing a traditional sailboat and a catamaran.
Understanding the Virgin Islands: US vs. British Territories
The Virgin Islands are divided into two main groups: the US Virgin Islands and the British Virgin Islands. The USVI includes St. Thomas, St. John, and St. Croix, while the BVI consists of around 60 islands, with Tortola, Virgin Gorda, Jost Van Dyke, Anegada, and Cooper Island being the most popular.
The USVI uses the US dollar, follows US laws, and English is the official language. The British Virgin Islands use the Eastern Caribbean dollar alongside the US dollar, and they have a British-influenced legal system. Both territories offer stunning beaches, excellent snorkeling, and vibrant local cultures, but the BVI is often considered more laid-back and less commercialized.
Travelers can easily visit both territories by boat, making a sailing trip an ideal way to explore the full range of what the Virgin Islands have to offer.
Top 5 Must-See Islands in the Virgin Islands
1. St. Thomas (USVI)
St. Thomas is the gateway to the US Virgin Islands and a hub for shopping, dining, and nightlife. The island is famous for its beautiful beaches like Magens Bay, which is perfect for swimming and sunbathing. Visitors can also explore historic Charlotte Amalie, known for its Danish colonial architecture and duty-free shopping.
What to do:
Snorkel at Coki Beach
Visit Coral World Ocean Park
Take a skyride to Paradise Point for panoramic views
Where to stay:
The Ritz-Carlton, St. Thomas for luxury
Emerald Beach Resort for a beachfront experience
2. St. John (USVI)
St. John is the smallest of the US Virgin Islands but offers some of the most pristine natural beauty. Over half of the island is protected as Virgin Islands National Park, filled with hiking trails, secluded beaches, and coral reefs.
What to do:
Hike the Reef Bay Trail to see petroglyphs and waterfalls
Relax on Trunk Bay, famous for its underwater snorkeling trail
Kayak through the mangroves
Where to stay:
Caneel Bay Resort for a classic island stay
Airbnb options for a more private experience
3. Tortola (BVI)
Tortola is the largest island in the British Virgin Islands and the main entry point. It offers a mix of beaches, hiking, and cultural sites. Cane Garden Bay is a favorite spot for both locals and visitors.
What to do:
Explore Sage Mountain National Park
Visit the Callwood Rum Distillery
Enjoy water sports at Cane Garden Bay
Where to stay:
Long Bay Beach Resort for a quiet retreat
Sugar Mill Hotel for a boutique experience
4. Virgin Gorda (BVI)
Virgin Gorda is known for The Baths, a unique geological formation of giant granite boulders creating natural pools and grottos. It’s a must-see for anyone visiting the BVI.
What to do:
Swim and explore The Baths
Hike to Gorda Peak for stunning views
Visit the Copper Mine ruins
Where to stay:
Oil Nut Bay for luxury villas
Bitter End Yacht Club for a sailing-focused stay
5. Jost Van Dyke (BVI)
Jost Van Dyke is famous for its laid-back vibe and beach bars. It’s a small island but packed with character, especially at White Bay, home to the legendary Soggy Dollar Bar.
What to do:
Relax at White Bay Beach
Enjoy live music and drinks at Foxy’s Bar
Snorkel at Sandy Cay
Where to stay:
Jost Van Dyke Villas for privacy
Local guesthouses for an authentic experience
Sailing Between the Islands: Choosing Between a Sailboat and a Catamaran
Speaking from first-hand experience, chartering a boat is one of the best ways to explore the Virgin Islands. It gives you the freedom to visit multiple islands, discover hidden coves, and enjoy the ocean at your own pace.
Sailboat
A traditional sailboat has a single hull and typically offers a classic sailing experience. It requires more skill to handle, especially in strong winds or rough seas. Sailboats usually have less space below deck but offer a more authentic sailing feel.
Pros:
More agile and responsive under sail
Classic sailing experience
Often faster in certain wind conditions
Cons:
Less living space and stability
Can heel (lean) significantly, which may be uncomfortable for some
Catamaran
A catamaran has two hulls, providing greater stability and more space. It’s ideal for couples, groups or families who want comfort and room to relax. Catamarans are less likely to heel, making them easier for beginners or those prone to seasickness. In our opinion, It's the best way to go.
Pros:
More deck and cabin space
Stable and comfortable ride
Easier to move around on board
Cons:
Slightly slower in light winds
Larger size can limit access to some smaller anchorages
Choosing between a sailboat and a catamaran depends on your sailing experience, group size, and comfort preferences. Both options allow you to explore the US and British Virgin Islands seamlessly.
Tips for Planning Your Virgin Islands Trip
Check entry requirements: USVI and BVI have different customs and immigration rules. Make sure your travel documents are in order.
Plan your itinerary: Decide which islands you want to visit and how many days to spend on each.
Book accommodations early: Popular resorts and villas fill up quickly, especially during high season.
Consider guided tours: For activities like hiking or snorkeling, local guides can enhance your experience.
Pack smart: Bring reef-safe sunscreen, snorkeling gear, and light clothing.
Final Thoughts on Exploring the Virgin Islands
The Virgin Islands offer a rare chance to experience two distinct cultures and island lifestyles in one trip. Whether you prefer the lively towns and beaches of the USVI or the tranquil, untouched beauty of the BVI, there is something for every traveler. Chartering a sailboat or catamaran lets you explore beyond the usual tourist spots and discover hidden gems. With stunning beaches, rich history, and endless activities, the Virgin Islands promise an unforgettable adventure.
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