One of the most popular regions to explore the stunning coastlines and vibrant cultures via super yacht is the Caribbean. Expect powder white sand beaches, tropical temperatures, and plenty of culture to experience. This region is a superyacht charterer’s dream. The cost to charter a yacht in the Caribbean will differ based on your destination, but expect to pay high season rates when chartering a luxury charter yacht in the Caribbean over the winter months.
Lying in-between the U.S. and South America with the Caribbean on its doorstep, historically this island has struggled to find its identity, but its rich heritage cannot be denied. Havana will captivate you with its colorful streets, vintage cars, and lively music echoing through the cobblestone streets. Explore the historic neighborhoods of Old Havana, sample authentic Cuban cuisine, and dance to the infectious rhythms of salsa under the starlit sky.
As you’re nudged along the trade winds to Cienfuegos, coined the “Pearl of the South,” you will be greeted by its stunning French colonial architecture and a vibrant cultural scene. Stroll along the Malecón and immerse yourself in the rich history and charm of this UNESCO World Heritage site. While it may appear as time has stood still here, that’s what makes a stop here on a luxury Cuba yacht charter so special.
The Cayman Islands, a group of three distinct islands, is an excellent choice for a superyacht charter. Grand Cayman, the most popular among expatriates and the financial hub of the region, offers various activities such as Stingray City, turtle farms and horseback riding on the beach. It also boasts numerous beach bars and restaurants to relax and enjoy a sundowner or two.
Cayman Brac is a haven for beach lovers with its stunning white sand beaches where you can swim ashore or ride a jet ski from your anchored yacht offshore. The island’s rugged beauty and impressive 140ft bluff are noteworthy features. Lastly, Little Cayman provides an atmosphere of understated luxury. As the smallest and least developed island stretching only ten miles long and one mile wide, it offers an ideal setting for those seeking tranquility and relaxation.
Miles upon miles of coastline define the island of the Dominican Republic. Expect palm-fringed pristine beaches, dramatic cliff faces, mangrove lagoons, and sweeping dunes. No other Caribbean yacht charter destination offers such a diverse range of landscapes. The island is well-known for its high-end luxury resorts, but its entire coastline is taken up, so there are still quite a few remote anchorages available. The towns, again awash with old Spanish colonial buildings, cobblestone streets, and horse-drawn carts, come alive with Merengue beats till dawn. Venture inland to enjoy quaint rural villages or spend lazy afternoons in shabby chic beach shacks drinking the local beer.
The Dutch Antilles is made up of Aruba, Bonaire, and Curacao. The trio of islands located just north of the coast of Venezuela seem to have more in common with South America than they do with the rest of the Caribbean. Therefore, a luxury Dutch Antilles yacht charter here offers a distinctly different vibe than other luxury yacht charters in the Caribbean. Firstly, the islands lie just off the hurricane belt, and benefit from tropical weather year round moderated by the trade winds, making them a delightful year-round destination. The upmarket resorts, high-end shopping, and pleasantly hued houses that the islands are famed for, make this an ideal place to charter a yacht in the Caribbean.
Island hopping, by definition, becomes an international affair during a luxury yacht charter in the Caribbean. From the North Caribbean and its rustic, old-world islands of the Bahamas, Turks & Caicos, Cuba, Dominican Republic, the Cayman Islands and Jamaica – where the focus is simply getting on island time and relaxing to the glitz and glamor of the southern Caribbean and the islands of The Leeward Islands, the Virgin Islands, Dutch Antilles and Windward Islands. This region is a superyacht charterer’s dream.
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Requests for crewed yacht charters in Jamaica have been on the rise as people seek the luxury yacht experience across various ports like Ochos Rios, Port Antonio, and Montego Bay. Jamaica offers something for everyone in your group. Picture yourself cruising along Jamaica’s sandy coastline on a luxury yacht as you take in one more exquisite sight after the other with the sunshine on your face. No matter the experience you seek in Jamaica, viewing it from the water provides a truly unique perspective on this sun-soaked and culturally rich country.
The Leeward Islands stretch from Puerto Rico in the north, south towards Dominica, encompassing the British and U.S. Virgin Islands, Antigua, St. Barths, Saint Kitts, and many other smaller islands. Each one offers something new for the Leeward Islands yacht charterer to explore, whether it be botanical gardens, glitzy beach clubs, coral reefs, or simply dream-inspiring beaches.
St. Barths has long been a superyacht destination thanks to the iconic St. Barths Bucket, a sailing regatta that is held here every March. Renowned for its upscale boutiques, gourmet dining experiences, and pristine beaches, you’ll definitely want to make time for a stop in Gustavia. French chic meets Caribbean charm as you leisurely stroll along the cobblestone streets or simply relax on deck as you soak in the beauty of your surroundings.
Sint Maarten (on the Dutch side) and St. Martin (on the French side) is another beautiful stop on your Caribbean yacht charter around the Leeward Islands. A popular port of entry and area to visit is Simpson Bay – with its crystal-clear waters and stunning coastline, it is a must-visit destination for yacht charterers. As you sail into Simpson Bay, you are greeted by the gentle sway of palm trees and the warm Caribbean breeze. The vibrant colors of the buildings lining the bay create a picturesque backdrop against the azure sky. It’s a scene straight out of a postcard, inviting you to immerse yourself in its beauty. Whether you choose to cruise around St. Martin or Sint Maarten, enjoy the temperate climate, gentle trade winds and plethora of island life to discover here on your luxury yacht charter in the Caribbean.
Boasting some of the most beautiful beaches in the world and set a mere 12 miles off the coast of St. Martin, Anguilla is just the dose of sunshine and pristine beaches you need on a private yacht charter in the Caribbean. From snorkeling in vibrant coral reefs to indulging in fresh seafood at beachfront restaurants, every moment spent in Anguilla is filled with luxury and relaxation. Whether you choose to anchor off a secluded beach for a private picnic or dock at a marina for a night of fine dining and entertainment, you can do it all in Anguilla.
When heading out on a crewed yacht charter in the Leeward Islands, make time to visit Antigua, with its unparalleled number of anchorages and 365 beautiful beaches to choose from, it’s easy to see why this is a favorite yacht charter destination for many. From the picturesque Falmouth Harbour, with its charming blend of history and modernity, offering a warm welcome to charterers from around the world, to English Harbour, you’ll be mesmerized by the stunning views of Nelson’s Dockyard, a UNESCO World Heritage Site that stands as a testament to Antigua’s rich maritime history.
Jolly Harbour beckons with its vibrant marina and pristine beaches, making it the perfect spot to drop anchor and soak in the Caribbean sun. Plenty of opportunities abound here to slap on the snorkel and fins, jump in the water to see the colorful coral and marine life up close, or take the water toys out for a spin across the bay.
Despite only being 100 miles long and 35 miles wide, Puerto Rico is a vibrant part of the Greater Antilles Island group. The region includes the main island of Puerto Rico, along with several smaller islands and cays like Vieques, Culebra, and Mona. The island’s rich Spanish heritage is prominently displayed through its colonial architecture, Latin fusion music genres, and captivating samba and salsa dances. San Juan serves as its bustling capital city located on the northern coast. This city offers a blend of grand architectural designs alongside a lively party scene, complemented by a rich cultural heritage showcased in various museums and forts.
The islands of the Turks & Caicos are located just south of the Bahamas and north of the Dominican Republic. In total, there are around 40 islands, with the main islands well-equipped for superyachts, with plenty of anchorage spots and a few good marinas. Middle Caicos and North Caicos are renowned for stunning vistas of lush green woodlands, cave networks, and stunning Flamingo ponds, both offering a vast range of plant and bird life. South Caicos has the natural phenomenon, the Boiling Hole, and is famed for its lobster and conch.
Yacht charters in the U.S. Virgin Islands offer a picturesque and exclusive experience, with the islands of St. Thomas, St. John, and St. Croix providing a luxurious backdrop for your adventure. These destinations are known for their upscale amenities and stunning natural beauty, giving you the feeling of being marooned in a tropical paradise. Located to the west of the British Virgin Islands, these islands offer a unique blend of relaxation and exploration for those seeking a truly unforgettable getaway on the water.
Immerse yourself in the pulsating nightlife of St. Thomas, where you may find yourself mingling with the stars. Or, let your spirit roam free amidst the stunning anchorages and sun-kissed tropical beaches of St. Croix. On your luxury Virgin Islands yacht charter, make time for the smallest island of St. John where most of the island sits within a National Park and its surrounding beauty.
A yacht charter in the BVIs is simply heavenly. This island chain is roughly split in half, separated by the Sir Francis Drake Passage. While on a British Virgin Islands yacht charter, the island of Tortola is must-see. Tortola offers many beautiful anchorages, including Cane Garden Bay, and its towns exude colonial charm with a Caribbean twist. Virgin Gorda is another popular superyacht destination, so be sure to include this gem in your itinerary. Whatever your reason for chartering in the Virgin Islands, there is little reason to leave its confines – from pirate history and fantastic shopping to an idyllic climate, excellent marinas, picture-perfect beaches, and a varied nightlife.
The Windward Islands of the Caribbean are located in the southeastern waters and include the islands of Martinique, St. Lucia, St. Vincent and the Grenadines, Dominica, Trinidad & Tobago, and Barbados as part of the island chain. This group of islands, also known as the Lesser Antilles, is considered the jewel in the Caribbean’s crown. Slightly less crowded than the Leeward Islands to the north, a luxury Windward Islands yacht charter offer a great tranquil escape on a Caribbean yacht charter.
One of the more popular yacht charter destinations in the Windward Islands is Martinique. From the picturesque Baie Du Marin to the slower paced and tranquil Bassin Tortue, every corner of this Caribbean island offers the chance to amaze you. Le Marin, known for its bustling atmosphere, well-serviced marina, and access point to the island, often serves as the perfect starting point for your yacht charter. You will witness Martinique’s diverse coastlines, hidden coves, colorful marine life, and numerous opportunities to snorkel or enjoy water toys. Setting sail from Le Marin is embarking on a voyage of discovery and delight! As you cruise along Martinique’s picturesque coastlines, let the vibrant marine life and enchanting hidden coves captivate your spirit. Dive into thrilling adventures with snorkeling and water toys, creating unforgettable memories along the way.
Immerse yourself in St. Lucia and witness the untouched beauty of Marigot Bay and the dynamic ambiance of Rodney Bay. Marigot Bay is often recognized as the Caribbean’s most beautiful bay, characterized by its serene turquoise waters enveloped by the island’s vibrant flora. This is where you can truly experience the stereotypical Caribbean yacht charter. Contrastingly, Rodney Bay offers a vibrant atmosphere with its lively waterfront eateries, colorful shops, and abundant nightlife options. St. Lucia effortlessly combines relaxation and excitement, filled with enchanting locations to fully immerse yourself in the untouched beauty and dynamic ambiance that a St. Lucia yacht charter offers.
St. Vincent & the Grenadines is a stunning destination with 32 islands offering a blend of natural beauty and tropical tranquility for a yacht charter vacation. From lush rainforests to pristine beaches with soft white sand, and vibrant coral reefs perfect for snorkeling, there’s something for every nature lover to enjoy. The Blue Lagoon Marina is a popular choice for many visitors, whether it’s for overnight berthing or to take advantage of the excellent facilities available in the area.
Dominica, the “Nature Island” of your yacht charter in the Caribbean, is fast becoming a hot spot for yacht charter vacations. Its deep anchorages and wild coastlines are a magnet for divers and hikers alike. Portsmouth, the island’s second-biggest town, is a popular pit stop for yachts cruising in the region. The anchorages are perfect for bigger yachts and offer quick access to cool spots like Cabrits National Park and Indian River.
Explore the stunning islands of Trinidad and Tobago on your next Caribbean yacht charter. These two gems offer a world as diverse as it is beautiful. Trinidad, with its electrifying atmosphere, rainbow-hued carnivals, and heart-thumping music scene – including the famous Trinidad Carnival – promises an unforgettable experience. On the other hand, Tobago is fast becoming a hotspot for eco-tourism enthusiasts. Its rich marine life invites snorkeling and diving adventures amongst colorful coral reefs; its verdant forests are perfect for bird watching; and its serene surroundings provide the ideal setting to relax after your exhilarating escapades in Trinidad. Upon docking at Chaguaramas, you’ll find well-equipped marinas ready to help you restock and refuel before you continue onto your next step on your Caribbean yacht charter.
Barbados may be a small island but there are plenty of things to do and see here on a Caribbean yacht charter. The crystal-clear waters are perfect for snorkeling on the coral reefs, scuba diving with colorful fish, paddle boarding, and jet skiing. On land, there are charming and vibrant sights to explore, from beachside bars to upscale dining options, high-end boutiques for shopping, and a variety of bars and clubs to enjoy at night. Bridgetown and Scarborough are great examples, with UNESCO World Heritage-listed sites like the historic Garrison area, the Parliament Buildings, and St. Nicholas Abbey, offering a glimpse into the island’s colonial past and some of the best nightclubs on the island.
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