Caribbean Island Chains: A Guide to the Leewards, the Windwards & Beyond

By: Motts Mueller, Broadreach Director March 14, 2025 Scuba, Sailing, Marine Biology

The Caribbean is a dream destination for adventure enthusiasts. This region offers a stunning mix of turquoise waters, lush landscapes, and vibrant island cultures. With so many beautiful island chains to explore, finding the perfect place to set sail can be challenging. Let’s break down some of the most iconic regions—the Leeward Islands, Windward Islands, British Virgin Islands (BVIs), U.S. Virgin Islands (USVIs), and ABC Islands—and discover each one’s unique charm.

The British Virgin Islands (BVIs): A Sailor’s Paradise with Some Downsides

The British Virgin Islands are one of the most well-known sailing destinations in the world. They feature protected waters, steady trade winds, and an array of easily navigable islands, making them an idyllic setting for both seasoned and novice sailors. With over 50 islands and cays, the BVIs are perfect for effortless island hopping. The BVIs are well-equipped with mooring balls, established marinas, and a flourishing charter industry.

While the BVIs offer stunning scenery and a relaxed sailing experience, it’s important to acknowledge that this accessibility does mean increased activity. Busy anchorages and a high volume of charter boats—many captained by less-experienced sailors—can create a lively environment. Nevertheless, for travelers craving picturesque views and easy exploration, the BVIs remain a fantastic choice. However, if a deeper cultural experience and more secluded escapes entice you, other island chains might better cater to your adventurous spirit.

• Highlights: Don’t miss The Baths on Virgin Gorda, the laid-back vibe of Jost Van Dyke, the wreck of the RMS Rhone, and the protected anchorages of Norman Island.
• Best For: This destination is ideal for beginners to sailing, those looking for easy navigation, and travelers who want a mix of snorkeling, beach bars, and historic shipwrecks.
• Drawbacks: While it’s beautiful, the BVIs can feel crowded, with a mix of experienced and first-time charter sailors navigating the waters. While there are excellent dive sites, the marine environments are not as diverse as elsewhere, and the culture and geology are less varied than the Leeward and Windward Islands. Furthermore, access from the U.S. may pose some challenges, with only one direct flight currently available.

The Caribbean Leeward Islands: A Blend of Cultures and Landscapes

Stretching from Puerto Rico to Dominica, the Leeward Islands present a vivid tapestry of cultures, vibrant port towns and dramatic volcanic landscapes. The mingling of French, Dutch, British, and African cultures creates an intriguing blend visible in the islands’ architecture, food and daily life. Few places can boast such a rich cultural and geological diversity in such close proximity.

For those seeking cosmopolitan destinations brimming with history and natural beauty, the Leeward Islands are a hidden gem. This region is a haven for scuba divers and hikers alike, offering world-class dive locations and stunning mountainous terrains. Whether it’s plunging into the crystal-clear waters surrounding Saba or hiking the summit of Statia’s dormant volcano, adventure awaits at every turn.

• Highlights: Be sure to explore the bustling port town of Gustavia in St. Barts, the world-class dive sites around Saba, the towering volcano on Statia, and the rich colonial history of St. Kitts.
• Best For: Perfect for those desiring a blend of cosmopolitan island life, history, and off-the-beaten-path adventure. Ideal for scuba divers, hikers, and those interested in cultural experiences.
• Drawbacks: Certain areas on St. Martin and St. Barts can feel commercialized, especially during peak seasons. Some islands in this region are small, and travel between them can depend on ferry schedules, which may restrict spontaneity.

The Caribbean Windward Islands: Untamed Beauty and Rugged Adventure

Located south of the Leeward Islands, the Windward Islands, stretching from St. Lucia to Grenada, showcase some of the Caribbean’s most pristine natural beauty. These islands feature dramatic landscapes, including towering peaks, lush rainforests, and volcanic terrain. At the same time, the dozens of small, often uninhabited islands that make up the Grenadines offer picture-perfect beaches with white sands, palm trees, and clear turquoise waters.

Though sailing conditions can be more challenging during the winter months due to stronger winds, the rewards are incredible: secluded beaches, vibrant coral reefs, and dramatic mountainscapes. Beneath the waves, the volcanic origins of these islands have resulted in steep drop-offs, intriguing lava formations, and thriving coral reefs, creating an underwater haven for divers. Discover Grenada’s immersive shipwrecks, Dominica’s dazzling geothermal vents, and St. Lucia’s breathtaking wall dives—each adventure is enhanced by the allure of fewer crowds compared to more tourist-heavy destinations.

• Highlights: Don’t miss the iconic Pitons of St. Lucia, the stunning beaches and crystal-clear waters of the Tobago Cays, the volcanic landscapes of St. Vincent, and the “Spice Island” charm of Grenada.
• Best For: Perfect for travelers seeking unspoiled beauty and a more adventurous, off-the-grid experience. Perfect for nature lovers, sailors seeking more open-water passages, and those interested in cultural immersion in local communities. It’s also excellent for scuba divers hoping to practice their drift diving in a secluded and pristine diving experience.
• Drawbacks: The Windward Islands are less developed, meaning fewer amenities and infrastructure. Some islands can be more challenging to access, with limited ports of entry and fewer tourist services.

The U.S. Virgin Islands (USVIs): A Mix of Convenience and Natural Beauty

The U.S. Virgin Islands, which include St. Thomas, St. John, and St. Croix, combine Caribbean beauty with the conveniences of being a U.S. territory. These islands offer stunning beaches, accessibility for U.S. travelers, and a mix of bustling and remote experiences.

St. Thomas is the most developed and lively of the three islands, while St. John is predominantly a protected national park. In contrast, St. Croix boasts a more relaxed atmosphere and rich historical charm, known for its significant role in the sugar trade.

• Highlights: Some must-see attractions include Trunk Bay’s pristine beach, the vibrant marine life around Buck Island, and the historic towns of Christiansted and Frederiksted on St. Croix.
• Best For: This destination is perfect for U.S. travelers seeking an accessible getaway that doesn’t require a passport. It offers both bustling and remote spots, and it suits those in search of exceptional beaches and scenic hiking opportunities.
• Drawbacks: Due to heavy cruise ship traffic and crowded tourist areas, St. Thomas can feel overly commercialized. While the snorkeling and beaches are fantastic, the dive sites here are not as renowned or varied as those in other parts of the Caribbean.

The ABC Islands: The Caribbean with a Twist

 

The ABC Islands—Aruba, Bonaire, and Curaçao—are located just off the coast of Venezuela and stand apart from the lush, tropical landscapes of the Windward and Leeward chains. These islands offer a different kind of Caribbean experience characterized by arid desert landscapes and a distinct Dutch influence.

Aruba is known for its white-sand beaches and vibrant nightlife, while Bonaire is famous for some of the best shore diving in the world. Curaçao, with its colorful Dutch colonial architecture and crystal-clear waters, is a cultural and historical gem. These islands lie outside the hurricane belt, allowing them to enjoy year-round sun and stability. This makes them an excellent destination for travelers seeking consistent sunny weather.

Broadreach’s trips in Bonaire and Curaçao ensure you experience the islands’ vibrant culture and unmatched diving opportunities!

• Highlights: Don’t miss the world-class shore diving in Bonaire, the historic city of Willemstad in Curaçao, and Aruba’s expansive beaches and lively resorts.
• Best For: The ABCs are perfect if you’re looking for year-round sunshine, exceptional diving, and a unique mix of Caribbean and Dutch culture.
• Drawbacks: The islands have a drier climate compared to other Caribbean destinations, resulting in less lush greenery and a more desert-like environment.

Which Island Chain Is Right for You?

If you’re looking for smooth sailing and a well-trodden tourist scene, the BVIs are an easy choice. If you want a mix of adventure, diving, and cultural experiences, the Leeward Islands offer a bit of everything. IF you crave a more remote and rugged journey, the Windward Islands provide the perfect challenge. If accessibility and convenience are key, the USVIs are a great pick. And for a unique Caribbean experience featuring top-notch diving and Dutch charm, the ABC Islands are a fantastic option.

No matter which region you explore, the Caribbean delivers unforgettable adventures above and below the surface. With Broadreach, you won’t just visit these islands; you’ll go beyond the well-known tourist hubs to dive into their history, marine life, and vibrant cultures in a way that few travelers do. Join us for an experience that goes beyond tourism and leads you into real adventure!