10 best yacht charter destinations in the Caribbean for the ultimate summer vacay

·19-min read

Picking from the most beautiful destinations in the Caribbean for the best luxury yacht charter vacation can be a difficult task simply because every island that is part of this remarkable geographic stretch is a tropical paradise. No wonder people from all over the world have the islands of the Caribbean on their travel bucket list.

The archipelago is located in the eponymous sea between the continents of North America and South America. It is a long chain of islands, starting from the west of the peninsula of Florida on the mainland US to the coast of Venezuela in South America.

The archipelago is divided into Lucayan Archipelago, Greater Antilles and Lesser Antilles. The northern islands of the Lesser Antilles are also known as the Leeward Islands, while the southern islands are known as the Windward Islands. Together, the entire geographic expanse is also known as the West Indies.

The culture of the region has been shaped by natives and the Europeans who arrived as traders, explorers or invaders. So, the Caribbean islands are a melting pot of cultures, from English to Dutch and from Spanish to French, and civilisations such as African, Latin American and Indian. Thus, food, festivals and music — including reggae, meringue and calypso to rumba and zouk — are the best reflection of this amalgam. The people are warm and friendly; they exude a joy for life that is instantly infectious and makes visitors truly enjoy the Caribbean to its fullest.

While all islands are accessible, some are magnets for the wealthy because of things like untouched natural landscapes and luxurious hotels and resorts.

However, the biggest draw of the Caribbean islands is the turquoise sea, spectacular white powder beaches, lush green inland forests, colourful birds, abundant marine life, spectacular corals, and the overall laid-back charm.

Tourism, therefore, is a major source of revenue for this region.

How to sail between Caribbean islands?

There are 13 independent countries and 15 dependencies in the Caribbean. Since they are located in a chain, island hopping in a luxury yacht charter is not only easy but also the best way to see the natural beauty of the Caribbean region.

Being a favourite holiday destination of the super-rich in the Americas, luxury yachts of all shapes and sizes, including superyachts and catamarans, can be seen anywhere on the waters of the Caribbean Sea. There is no dearth of yacht charter services offering their best boats for rent for vacationers in the Caribbean.

The type of charter booked decides how the experience will be. A superyacht can easily go anywhere at a high speed but needs to anchor in deeper waters from where its tenders can take guests to secret coves and lagoons in shallow depths. Sailing yachts are slower but can usually reach shallower depths. If space and diving into the blue waters from the deck are on the mind, a catamaran might be the best choice.

9 best private yacht destinations in the Caribbean

The British Virgin Islands

Yacht Charter Destinations In The Caribbean
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The British Virgin Islands (BVI) is a heavenly archipelago of over 50 isles and four large islands, each more spectacular than the other. The region is a magnet for Caribbean yacht charters, with everyone from celebrities to billionaires bringing their huge boats to this place.

Virgin Gorda, one of the four large islands, is particularly famous for the Baths — a network of grottoes and saltwater pools created by volcanic activity. It boasts the finest white sandy beaches in the Caribbean to walk on, as well as luxury resorts for those who want to sleep on land.

Between Peter Island and Salt Island is the Rhone Marine Park, a popular dive site for the 19th-century wreck of the sail-steamer named HMS Rhone. And if the idea of a seafarer’s adventure is on the mind, then a dinghy ride on the Deadman’s Bay towards the Dead Chest Island is the thing to do. The island and the bay are believed to have got their names when the crew of the legendary pirate Blackbeard died in their attempt to swim across to Peter Island.

Tortola, the largest of the islands, and the Dutch-named Jost Van Dyke are perfect for hangouts off the yacht. The former is renowned for its nightlife and the latter has Soggy Dollar Bar, which is known for creating the Painkiller cocktail.

The closeness of the islands makes the archipelago perfect for island-hopping even in a catamaran with friends or family and children.

Barbados

Barbados
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Barbados is renowned for its outstanding hospitality, which makes visitors feel at home. Its unique geographic position as the first Caribbean island from Africa and Europe is one of the major reasons behind its composite African, European and Indian culture, which is especially reflected in its cuisine.

A fantastic island for a trip on a private yacht in the Caribbean, Barbados is ideal for scuba diving among corals, ambling about on soft sand beaches, or even swimming in the turquoise blue waters. Visitors can also book a ride in a specially designed submarine to explore shipwrecks.

The home of pop superstar Rihanna and several cricketing legends, life in Barbados is always pulsating with music, dance and sports. Many of its buildings date back to the British colonial times, best seen through a tour of the UNESCO World Heritage Site of Historic Bridgetown and its Garrison.

Sites such as Harrison’s Cave formation are among its well-kept natural wonders. There are well-maintained botanical gardens, such as the Andromeda Botanic Gardens and plantation houses such as the 17th-century St. Nicholas Abbey. These land-based features make Barbados one of the most attractive wedding destinations in the Caribbean.

The best way to retire to the yacht after a trip to Barbados is to get a bottle of local rum, which Barbadians call their oldest and greatest export.

Jamaica

Yacht Charter Destinations In The Caribbean
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Those who want to experience a horse ride through the waves of the sea should head to Jamaica. It is one of the most famous Instagram moments for tourists who come to this island located south of Cuba between the Cayman Islands and Haiti.

One of the major island nations of the West Indies, Jamaica and the surrounding waters can be easily explored in a private superyacht charter designed for navigating Caribbean waters.

For those who love measuring the waves, Jamaica plays host to the internationally renowned Makka Pro Surf Contest — the region’s largest surfing event. Even if one is not a pro, surfing at the Palisadoes Strip in the capital Kingston or the Boston Beach are must-do activities.

However, Jamaica is significant as the perfect snapshot of Caribbean cultural amalgamation. It offers the very best in music, food, history and natural wonders in the entire region. Jamaican Maroons, a term for those who freed themselves from slavery, developed a process of secretly cooking pork underground to prevent smoke from emanating. The method, known as “jerking,” is today used to prepare everything from chicken to fish in Jamaica.

Reggae has its roots here, immortalised globally in the voice of Bob Marley. There are beach bars, reggae clubs and discos across Jamaica, and a quick way to experience the nightlife would be to spend a night in the capital city of Kingston.

The interior of the island is mostly mountainous and boasts spectacular hiking destinations such as the UNESCO World Heritage Site Blue and John Crow Mountains National Park.

St. Vincent and the Grenadines

Yacht Charter Destinations In The Caribbean
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It gets its name from the main island of St. Vincent and 32 other remote islands and cays, which are part of the Grenadines chain of islands, to its south. The entire island chain stretches around 65 km in length.

Considered one of the finest Caribbean sailing destinations, the best way to explore the island chain is to chart a week-long yacht course that can cover around 145 km of cruising. The islands are close, with distances ranging between two and five hours. Yachts can anchor anywhere on the nine inhabited islands of St. Vincent, Young Island, Bequia, Mustique, Canouan, Mayreau, Union Island, Palm Island and Petit St. Vincent. Each of them has quaint local restaurants and clean beaches for yachters to unwind.

St. Vincent and the Grenadines offer more than 100 dive sites for both casual and seasoned scuba divers. Everything from shipwrecks to coral reefs and dive walls to naturally created underwater gardens can be seen deep under the turquoise waters of the islands. An array of marine life thrives undisturbed in the underwater caves and canyons created by millions of years of volcanic activity that has shaped the geology of much of the region.

Visitors can also snorkel in the waters of the remote and uninhabited protected marine park of Tobago Cays, which has five islets and a giant horseshoe reef.

For those who like to explore singular islands instead of cruising, the main island, St. Vincent, could be the ideal stop. It is an eco-tourism hub, whose lush green vegetation has made it the ideal home for birds such as hummingbirds, whistling warblers and the endemic St Vincent Parrot. Trails such as the Vermont Nature Trail help visitors come close to nature and the free-flowing inland waterfalls that mark the island’s natural landscape. Hikers, however, particularly love going up the 1,220 metres tall La Soufriere, an active volcano which even mesmerised the acclaimed 18th-century English novelist Daniel Defoe.

If there is time for a bit more sailing, the towering pitons of the island country of St. Lucia are just north of St. Vincent. The two pitons, which are volcanic plugs, are a UNESCO World Heritage Site and are close to secluded resorts of St. Lucia.

Trinidad and Tobago

Trinidad
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The two-island country is the southernmost of the Caribbean islands and lies close to Venezuela. Its natural resources, particularly oil, have made Trinidad and Tobago a high-income economy and one of the richest countries in Latin America and the Caribbean.

Trinidad is the larger of the two and is where the capital, Port of Spain, is located. It is best known for numerous festivals, including the electrifying Carnival, which is held annually in February and has revellers gyrating to the tunes of calypso.

There are also pristine beaches, such as Mayaro, Trinidad’s longest beach, which are perfect for tourists to take long walks on. The Venezuelan coastline is visible across the rocky formations off the golden sands of Columbus Bay beach and, if visiting between March and August, there is an opportunity to see leatherback turtles lay their eggs on the beach of Blanchisseuse and Grande Rivière.

The secluded Macqueripe Bay beach should be on the itinerary of a private yacht in the Caribbean. The water here is excellent for swimming, and there is a seven-course zip line that takes visitors through the rainforest and offers unparalleled views of the Caribbean Sea.

Also on the island are numerous biodiversity-rich areas. Chief of these is the Asa Wright Nature Centre, which is a former cocoa and coffee plantation area transformed into a nature reserve and home to numerous species of birds.

Tobago, on the other hand, is smaller than Trinidad but has a much-deeper cultural footprint. Literature lovers believe that this tobacco-pipe-shaped island was the inspiration behind not one but two iconic classics in English literature — Defoe’s Robinson Crusoe and Robert Louis Stevenson’s Treasure Island. In fact, so strong is the association that the adventure classic Swiss Family Robinson (1960), which was based on the 19th-century book of the same name by Johann David Wyss, was filmed on the Bacolet Bay beach in Tobago.

Nature also rules over Tobago more than it does over the economically developed Trinidad. While its Pigeon Point beach is considered one of the best in the world, the Tobago Main Ridge Forest Reserve is the oldest rainforest concentration in the Western Hemisphere.

Cayman Islands

Cayman Islands
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There is something for everyone in the Cayman Islands, including children. The coral sand-covered Seven Mile Beach on Grand Cayman, the largest of the three islands that make up the Cayman Islands, is particularly famous for being one of the safest beaches for swimming. There are also opportunities for kids to take their first lessons in scuba diving.

The island is a magnet for the rich, which is why there are high-end luxury fashion stores of brands such as Gucci and Versace in George Town, the capital city located on the Grand Cayman island. And there is no dearth of gourmet restaurants and luxury resorts on Grand Cayman, should one choose to stay and dine on land.

Little Cayman and Cayman Brac, the other two islands, are more off the beaten track. Although both are known for their secluded environment, they offer dramatically different pleasures for thrill-seekers.

The beaches on Little Cayman are mostly empty, making it the best place to do meditation on the soft sand while listening to the music created by the rustling of the palm trees. The stunning blue water of the South Hole Sound Lagoon on the island is incredibly alluring for swimmers. Divers find a true challenge in the Bloody Bay Wall Marine Park, which has a reef with a dramatic drop-off of more than 1,500 metres.

Cayman Brac, on the other hand, looks stunning even from a distance from the yacht itself. This is because of its magnificent bluff — a cliff-like natural formation that towers over the sea. The Brac, as it is also called, is famous as a fishing location as much as it is for diving.

However, no tourist who comes to the Cayman Islands misses a visit to what is popularly called ‘Stingray City’. In reality, an array of sandbars located a few kilometres off Grand Cayman, Stingray City is the world’s best place to swim with friendly stingrays. In fact, visitors can see the beautiful marine creatures float about from the deck of their Caribbean luxury yacht charters.

Dominican Republic

Yacht Charter Destinations In The Caribbean
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Sailing vacations in the Caribbean would be incomplete without a tour of the Dominican Republic, which is one of the richest countries in the region. It shares the island of Hispaniola with Haiti to its west and its shore is washed by waters of both the Atlantic Ocean and the Caribbean Sea.

Being the second-largest island nation in the Caribbean after Cuba, Dominican Republic offers a much wider scope for fun, leisure, adventure and relaxation for visitors. In fact, it is perhaps a guarantor of the most complete Caribbean experience for those navigating the Caribbean Sea in style in a private superyacht.

The 1,600-km coastline has more than 200 beaches of mostly white sand, including several that are free of crowds. The most famous of these is the 48-km stretch of beaches along Punta Cana, at the eastern point of the island. Mooring the yacht here opens a universe of thrilling water sport activities such as kiteboarding. There are more beaches on the northern side, along the Atlantic coast, than those on the southern side, along the Caribbean coast. However, the latter offers calmer and safe waters for swimming all year round.

The Dominican Republic is also renowned as one of the finest golfing destinations in the Caribbean and Latin America. It has 26 designer golf courses with features such as coastline, mountainous terrain and green fairways. Some, such as the golf course at Los Corales, have even hosted the PGA Tour.

The large landmass gives the Dominican Republic a diverse landscape and climate, which helps over 6,000 species of flora and fauna thrive on land and the waters of the country. Tropical jungles, mangroves, mountains and valleys span national parks and reserve areas. The Jaragua National Park, the largest of all, is part of the UNESCO Biosphere Reserve of the Dominican Republic and includes beaches, lagoons, dry forests and cays. While the Sierra de Bahoruco is the region’s only cloud forest, the tall rock formations of Los Haitises National Park can be best photographed from a yacht.

History buffs can visit the UNESCO World Heritage-listed Colonial City of Santo Domingo is a must. It was founded in 1498, six years after Columbus’ arrival on the island and is the site of the first cathedral, hospital, customs house and university in the Americas. It is, therefore, the oldest continuously inhabited European settlement in the Americas.

A glimpse of its cultural contribution can be experienced with a visit to the small village in Puerto Plata, believed to be the birthplace of the world-famous dance form known as merengue. The island nation is as famous for its cigars and the Dominican drink known as Mama Juana, which is made by mixing rum, red wine and honey.

The Bahamas

The Bahamas
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With 16 major islands, The Bahamas is a world-class archipelago tailored for a long luxury Caribbean yacht charter cruise. Whether it is Andros or The Abacos or The Berry Islands, or Nassau & Paradise Island, the soft sand beaches are washed by blue waters all through the length and breadth of the chain of islands.

Some of the islands are uninhabited and, therefore, serve as eco-tourism hubs. The island of Inagua, for instance, has three national parks and is home to more than 80,000 pink flamingoes — one of the two national animals of the country. There are also over 140 species of native and migratory birds.

One of the most peculiar tourist attractions in The Bahamas can be found on the island known as The Exumas, which is composed of 365 small islands. Its claim to global fame is the uninhabited Big Major Cay, where visitors can swim with and feed about 20 cute pigs. Yet, The Exumas is a favourite haunt of celebrities because of the relative isolation of the islands and cays, undisturbed beaches, underwater caves of Thunderball Grotto and ultra-exclusive resorts.

As for beach lovers, they might want to opt for a stay on Harbour Island for its breathtakingly beautiful Pink Sand Beach, which gets its name from the pale pink colour of the sand. Patrons of art can explore the art galleries in Nassau and see how young artists are transforming The Bahamas one painting at a time. History buffs can visit San Salvador and pose at the exact location of Christopher Columbus’ first landfall in the Americas at what is now Long Bay.

Those who are adventurous should chart a course for Long Island to dive into the Dean’s Blue Hole, the second deepest blue hole in the world after Yongle Blue Hole in the South China Sea.

Of all the natural attractions in The Bahamas, the one that perhaps dominates Instagram feeds of tourists is the ocean-themed resort named Atlantis on Paradise Island. It boasts the world’s largest open-air marine habitat besides a number of superb water slides. There is no dearth of accommodation or restaurants on Paradise Island. Visitors can just park their yacht at the harbour of Atlantis Marina and head for the resort hotel named The Royal. Other options include luxury villas of Harborside Resort and sophisticated suites of The Cove.

US Virgin Islands

Yacht Charter Destinations In The Caribbean
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A territory of the United States, the US Virgin Islands is nicknamed “America’s Paradise,” and for a good reason. Comprising four principal islands – St. Croix, St. John, St. Thomas and Water Island – and 50 smaller islands, cays and islets, there is never a dull moment in the US Virgin Islands.

The weather is ideal almost throughout the year for sunbathing on the beach. With White sand beaches and turquoise waters, each island offers unique experiences to visitors. St. Croix showcases its colonial heritage and history through its forts and plantations. Close to it is the cay known as Buck Island Reef National Monument, which is an excellent diving spot among corals.

Northwards, on the island of St. John are the best of the beaches, many accessible only by hiking, and protected park areas such as Virgin Islands National Park known for its nature trails. This is the island most famous among honeymooners for its natural beauty.

To its immediate west is St. Thomas, which is also known as ‘Rock City’ due to its rocky geographic landscape. Tourists can leave their superyacht among the other charter yachts at the island’s harbour and climb the mountain on the island overlooking Magens Bay to see one of the finest panoramic vistas in the Caribbean.

St. Kitts and Nevis

Yacht Charter Destinations In The Caribbean
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Seasoned travellers call St. Kitts and Nevis the hidden gem of the Caribbean for its incredibly unspoilt landscape marked by clean beaches and clear waters. Although it is the smallest country in the region, its charm as a Caribbean yachting vacation destination stands out from the rest.

While the dual-island has all the shore characteristics of other Caribbean islands in its topography, it also boasts a unique black sand beach along the Dieppe Bay on the island of Basseterre of St. Kitts. The beach is where the Atlantic Ocean meets the Caribbean in this part of the world. The black sand of the beach has its origin in the long-dormant Mount Liamuiga volcano, which has a crater lake at its peak and is an excellent hiking destination.

St. Kitts and Nevis is also the only country in the Caribbean with a functioning railway. Known as the St. Kitts Scenic Railway, the small but beautiful train takes passengers on a three-hour tour through some of the finest Instagram-worthy spots on the beautiful island.

Its history is marked by the UNESCO World Heritage Site of Brimstone Hill Fortress, which is made from stone carved out of the volcanic rock of the island. Overlooking the Caribbean Sea, it is one of the earliest examples of the polygonal style of fort constructions.

For unwinding, tourists might try their luck at any of the 100 slot machines and electronic tables of Blackjack and Roulette at the Royal Beach Casino — one of the largest in the Caribbean.

(Hero and featured image credits: Denys Nevozhai/Unsplash & Fernando Jorge/@fx24/Unsplash)

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