10 Off-the-Beaten-Path Caribbean Yacht Charter Destinations 

When winter arrives, the Caribbean is one of the go-to, iconic yacht charter hotspots for tropical escapes to the many islands. And while superyachts usually flock to the hangouts of places such as the BVI’s, Bahamas, and St Barths—there are plenty of lesser-known islands that are perfect for those looking to get more off the beaten path. 

A popular cruising ground, the Caribbean typically conjures up images of bustling marinas and full anchorages, but there are still corners of this sea where you can head with fewer crowds, secluded anchorages, and more authentic and unique experiences ashore. 

Caribbean yacht charters today are shifting in terms of what guests are now demanding, from wellness-focused to more experiential itineraries and lower-impact charters. These off-the-beaten-path Caribbean islands can offer changes in preferences, increased privacy, and exclusivity without requiring a trip to those more far-flung locations. 

To discover a more unique Caribbean yacht charter far from the crowds, here are the islands to put on your must-visit list: 

Dominica

Often nicknamed the ‘Nature Island’ of the Caribbean, Dominica (not to be confused with the Dominican Republic), is an untamed paradise offering an authentic Caribbean adventure. Rainforests, volcanic peaks, and cascading waterfalls dominate the landscape, making it ideal for an adventure-filled itinerary.

Hiking is celebrated with trails in the UNESCO-protected Morn Trois Pitons National Park and a chance to spot the island’s national symbol: the endemic Sisserou parrot. Under the water, Dominica is an excellent location for snorkelers and scuba divers. 

Anchoring in a secluded bay, or off one of the most incredible beaches like Batibou Beach, for the day perfectly complements the adventurous itineraries. Dominica, the last island in the Eastern Caribbean to be colonized, offers opportunities to meet the indigenous Kalingo people – the last Caribbean community claiming direct descent from pre-colonial inhabitants. 

Les Saintes, Guadeloupe

A small collection of islands just south of Gradelope, Les Saintes, reflects authentic French Caribbean charm and beauty. These small, hilly yet secluded islands are peppered with pastel-colored houses, surrounded by turquoise waters and idyllic beaches.

Undiscovered by the masses and with only two of the islands inhabited, you can easily get away from it all here, welcomed in by the island’s warm embrace. Anchor in hidden coves and explore the many beaches, such as Pain de Sucre and Grand Anse, Ashore, soak up the history and culture influenced by French and Caribbean traditions. Combine a yacht charter itinerary with exploring the nearby Guadeloupe. 

Little Cayman, Cayman Islands

The smallest and least populated of the three Cayman Islands, Little Cayman is a lesser-visited destination in the Caribbean. A British Overseas Territory, it is renowned for its pristine beauty and undeveloped landscapes, offering serenity that is hard to find elsewhere. 

At just 16 kilometers long, yacht charters can explore the island like their own, giving off the perfect Castaway vibes. Enjoy the mostly deserted, soft and sandy beaches, including the pink-tinged Point O’Sand. Nature is abundant here, from the endemic rock iguanas to tropical birds. Keep an eye out for the largest colony of Red-footed Boobies in the Western hemisphere, at the Booby Pond Nature Reserve. 

But the true pièce de résistance of the island is what it offers beneath the surface. Diving sites like the vertical drop-off at Bloody Bay Wall are not to be missed. The diving here is truly world-class, with other notable sites including Jackson’s Bight, renowned for its tunnels, and Eagle Ray Roundup, which is home to multiple spotted eagle rays.

Bocas Del Toro, Panama

On the northwest of Panama, close to the Costa Rica border, is Bocas Del Toro. A group of islands belonging to Panama, and an under-the-radar Caribbean gem. Typically beginning a yacht charter on the Isla Colon at the Red Frog Beach Marina, there is plenty to include on a yachting itinerary. 

Water-based fun includes some of the best surfing spots in the Caribbean. The Isla Bastimentos National Marine Park is home to biodiverse marine life and an array of scuba diving and snorkelling action. Ashore, you can enjoy the white sandy beaches and authentic, laid-back Caribbean atmosphere.

There are plenty of ecotourism operations run from these islands, including rainforest hiking and opportunities to visit cocoa farms and local, small-batch chocolate producers. Feeling relatively remote, while still easily accessible for yachts, Bocas del Toro offers an experience that feels far from other, built-up Caribbean islands. 

Belize

Further north from Panama is Belize, along the coast of Central America. Belize remains relatively under the radar for yachting, offering a unique charter experience that is full of incredible diving, rich cultural history, and a whole host of activities ashore. 

With a 240-mile coastline and over 400 islands and coral atolls, there is plenty to fill up an itinerary. Include postcard-perfect and unspoiled locations like Goff’s Cay, Turneffe Atoll, and South Water Caye, as well as the first marine protected area in America, Half Moon Caye. 

Committed to conservation, around 40% of Belize is protected as a park or reserve, and it is home to the UNESCO-protected second-largest reef in the world, the Mesoamerican Reef System, which gives rise to numerous world-class diving experiences, including the famous 1000-foot Blue Hole. 

When exploring Belize, visit cocoa plants, charming seaside towns, explore well-preserved Mayan ruins, cruise up rivers, and enjoy various rainforest-led adventures.

Nevis, St Kitts & Nevis

The quieter sibling of Saint Kitts, Nevis, is part of the Leeward Islands and offers the perfect Caribbean escape. The towering Nevis Peak, a dormant volcano surrounded by rainforest, provides the most dramatic backdrop, bordered by golden beaches and calm waters. 

The coastline is perfect for those seeking solitude in tranquil and secluded anchorages, as well as for hopping ashore to visit the beautiful beaches. Nevis’ charm extends inland, where charming colonial architecture and boutique hotels reside in restored sugar plantations. Outdoor enthusiasts can enjoy the rainforest trails, the botanical gardens, horse riding along the beach, and relax in the natural hot springs. 

Montserrat

Montserrat, also known as the “Emerald Isle of the Caribbean,” lives up to its moniker with its lush green hills and connection to Irish heritage. The volcanic island is home to the active Soufriere Hills volcano, and in the north, dense rainforests. 

Its volcanic history is evident when visiting the abandoned capital of Plymouth. Today, no one inhabits the ash-covered capital, and a guided tour can be taken safely through the exclusion zones. And, most of the islands’ beaches are black sand, except Rendezvous Bay. 

There are also several trails available for those who want to explore the rainforest, visit old banana plantations, and admire the sea cliffs. Just a stone’s throw from Antigua, combining a visit to Montserrat with a wider itinerary is recommended. 

The Grenadines

Flung between St Vincent to the north and Grenada in the south are The Grenadines, a string of small islands embodying what many dub the ‘true Caribbean.’ Each island has its own personality, from the quiet elegance and celebrity hideout of Mustique and Canouan to the quaint charm of Bequia and Union. 

The island’s relaxed pace and welcoming communities offer a sense of intimacy that larger, more populated islands often lack. Ideal for sailing conditions and protected bays, anchoring here allows you to enjoy the diverse underwater world, visit turtle hangouts, explore colorful villages, and unwind on the nearby beaches. 

The ABC’s

Aruba, Bonaire, and Curacao are located within 50 miles of each other, offering an off-the-beaten-path experience that combines Caribbean culture, rugged landscapes, and ideal sailing conditions. 

Each island boasts its own benefits. Aruba is for beach lovers with its golden beaches and lively towns, and the sheltered bays are perfect for a yacht charter itinerary. While Bonaire is a diver’s haven with abundant marine life and reefs. The largest of the islands and full of Dutch colonial architecture, Curacao is great for hiking ashore and refueling with local cuisine. 

Cuba

Historically less accessible due to political and regulatory restrictions, Cuba is one of the Caribbean’s intriguing yet less-traveled destinations. With relatively limited yachts visiting, Cuba has remained largely undeveloped in terms of yachting itineraries. 

The island’s charm is rich in colonial architecture, local music, art, and cuisine, as well as remote anchorages and tranquil bays. The crystal-clear and warm waters are perfect for diving, swimming, and snorkelling with reefs teeming with marine life. Cuba offers an exciting combination of history, beauty, and authentic culture for those looking for an off-the-beaten-path Caribbean experience.