Greater Antilles Yacht Charter

Greater Antilles Yacht Charter Guide

Combining the larger Caribbean Sea islands like Cuba, Puerto Rico, Jamaica, and the Cayman Islands, the Greater Antilles are the undisputed jewel of the region.

From the regal crumbling facades and hazy cigar smoke of Cuba to the Spanish and Caribbean mashup on the shores of Puerto Rico, the Greater Antilles offers endless cultural charm for yacht charter guests.

For those seeking natural wonders, the world’s largest coral reef fringing the shores of Cuba, Puerto Rico’s pristine beaches and lost islands, and Jamaica’s Blue Mountains and bioluminescent bays open an Indiana Jones-like world of adventure.

Yachts in the Greater Antilles

Motor yachts
Sailing yachts

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A Greater Antilles yacht charter is a unique and luxurious experience offering the best of the two worlds: a wild adventure in the Caribbean combined with the comfort and freedom of travel only a luxury yacht charter can offer.

Explore the Greater Antilles charter yacht options today and start planning a trip of a lifetime.


Coconut saler walking by the sea in the famous Juan Dolio Beach of Dominican Republic
Stingrays at stingray city in Grand Cayman Islands
Colorful street in Old Havana with the Presidential Palace on the background

Reasons To Charter A Yacht In The Greater Antilles

Chartering a yacht in the Greater Antilles promises an unforgettable journey filled with rich cultural experiences, stunning nature, a touch of history, and old-world charm.

Here are our top reasons to charter a boat in the Antilles:

Cultural Flair

Puerto Rico is where Spanish flair meets Caribbean charm, and the melding of these two cultures comes together in an explosion of color, cuisine, and music.

From the heady scent of a roasted suckling pig wafting down the street to the energetic pulse of salsa beats spilling out into the night, the sleepy afternoons meandering down historic cobbled streets, wild weekend festivals, and rainbow-painted homes, Puerto Rico doesn’t shy away from her roots.

Cuba is alive and kicking: timba bands, sultry salsa nights, and Spanish flamenco can pour out of every window in the neighborhood, and the live music scene in Havana is as rich and rewarding as it gets.

Finally, there’s Jamaica with its rhythms of reggae, lively markets in Ocho Rios, and endless impromptu parties in Montego Bay.

Beautiful Beaches

A vision of vivid perfection, the white sand beaches of Puerto Rico capture that Caribbean charm – with an added edge.

Wonder-stricken Yacht charter guests will be wonder-stricken at the sight of golden sands and blue seas ebbing against a landscape of colonial-painted prettiness and lush green backdrops.

Some of the beaches and coves around Puerto Rico are home to bioluminescent waters, where it appears as though a thousand stars have fallen into the sea.

Historic Weight

Stories of sieges, crumbling empires, fallen sugar refineries, and pre-colonial ruins curate a fascinating picture of settlers, swashbucklers, and smugglers in Puerto Rico.

If you leave your yacht charter behind for a trip to Cuba, be sure to make it to the UNESCO reserve of the Vinales Valley. These prehistoric lands are said to be the oldest region in the whole of Cuba – even dating right back to the Jurassic period. This is a great place to go horseback riding, especially if you want to see the sprawl of tobacco and coffee plantations.

Over in Jamaica, vibrant street art, the history of reggae, and the Bob Marley Museum are all worthy of exploring.

Rafting on the White River in St Ann, Jamaica
Mountains Over Haiti
A diver explores the cracks, crevices and holes in a coral reef

Where To Visit In The Greater Antilles

The Greater Antilles are a treasure trove for charter yachts: warm waters, paradise beaches, the natural beauty of the islands, and pleasant weather provide a perfect backdrop for yachting adventures.

Rich culture, history, and colorful local traditions add flair to the sailing experience, while the island’s intriguing past, delicious cuisine, and music scene make it an ideal destination for a vacation filled with local Caribbean charm.

Below, we list our favorite Greater Antilles boat charter destinations:


A destination that effortlessly blends seafaring luxury with cultural richness, the nostalgia of Old Havana, and pristine coastlines, Cuba has long fascinated travelers with its mystique.

Home of painted grand avenues, crumbling squares, classic cars, and a whirlwind of sights and sounds, Havana is achingly romantic. Leave your yacht charter at the dock and head to the historic center to wander in the shadow of great buildings. Admire the thriving art scene that is taking the city by storm and sip a Cuba Libre at the Hotel Nacional de Cuba. Finally, it may be a tourist attraction, but don’t leave the city without a ride in a classic car.

Cuba’s long coastline of pristine white sand beaches and crystalline waters provides an alluring canvas for yachting enthusiasts: from the serene beauty of the Jardines del Rey archipelago, the dramatic cliffs of Trinidad, and the dazzling beaches of Varadero to the bustling marinas of Havana, the island's geography offers a range of experiences.

Here, lush rainforests and swamplands give way to breathtaking coral reefs: Jardines de la Reina, a marine reserve and a UNESCO World Heritage Site, is a paradise for divers and snorkelers where sea turtles and pristine coral formations abound.

Puerto Rico

Sitting right at the crossroads of the Caribbean Sea, Puerto Rico is a beautiful island serving as the perfect launchpad for the Greater Antilles luxury yacht charters. An easy distance from the Virgin Islands, the Lesser Antilles, and the Dominican Republic, Puerto Rico’s San Juan marina is the ideal yachting hub for the region.

Boasting a spectacular coastline of 270 miles of secluded coves, bioluminescent bays, and bustling coastal towns, Puerto Rico is the perfect place for a sailing vacation. Blending Taino, Spanish, African, and American influences, Puerto Rico boasts a unique cultural fusion resulting in colorful festivals, a fantastic music scene, and mouth-watering cuisine.

San Juan, the capital, is a UNESCO World Heritage Site with its charming old town, cobblestone streets, and well-preserved forts. Discover the rhythm of salsa music in Ponce or explore the art scene in Rincon. Down in Old San Juan, luxury yacht charter guests will find one of the most strikingly well-preserved examples of Spanish colonial architecture. Take a walk up to the Castillo San Felipe del Morro, sip locally grown coffee at one of the chic little cafes lining the streets, and have dinner and drinks at one of the Michelin-starred spots. For the edgier traveler, a street graffiti tour and an evening of island-invented Pina Coladas could be an alternative menu.

Nature lovers will enjoy Puerto Rico’s El Yunque National Forest, the only tropical rainforest in the U.S. National Forest System, brimming with lush foliage, cascading waterfalls, and exotic wildlife.

For marine enthusiasts, Puerto Rico's underwater wonders are a treasure trove. Snorkel off the coast of Culebra and encounter vibrant coral reefs, sea turtles, and colorful fish. In the northwest, Flamenco Beach ranked as one of the top beaches in the world, is a postcard-perfect horseshoe stretch of white sand and turquoise waters.

For luxury yacht charter guests seeking exquisite experiences, the privately owned Palomino Island offers an upscale getaway.


Often dubbed the “Jewel of the Caribbean”, Jamaica is an increasingly popular Caribbean yacht charter destination. Its diverse coastline featuring serene coves, lush greenery, and tranquil anchorages creates a perfect backdrop for sailing, while the famous Seven Mile Beach serves up stunning sunsets ideal for a special occasion.

Jamaica’s captivating cultural tapestry of reggae music, street art, and delicious cuisine offers authentic local experiences. The birthplace of Bob Marley, the island is equally famous for its Blue Mountains rainforests and the exquisite Blue Mountain Coffee.

Finally, Jamaica’s Luminous Lagoon in Falmouth is the brightest bioluminescent bay, where tiny microorganisms create a mesmerizing glow in the dark waters.

When To Charter A Yacht In The Greater Antilles

The best weather in Puerto Rico can be found during the winter months when the sun, sky and sea all remain bright, clear-eyed, and blazing. Over in Cuba, late spring and early summer are swell times to visit if you are seeking warm weather and lazy beach days.

The Cost of a Greater Antilles Yacht Charter

Caribbean yacht charter prices depend on the size, type, and capacity of the boat.

A motor yacht or catamaran for 6-8 people, for example, costs between $20,000 and $35,000 per week. A boat rental for a bigger group might cost between $50,000 and $150,000 a week, especially if you’re looking at luxury yacht charters. When it comes to the private charter of superyachts, except to shell out $800,000 and upward.

Find Greater Antilles Yacht Charters That Offer the Right Features

A Greater Antilles yacht charter is a luxurious escapade that offers the freedom to explore one of the world's most idyllic destinations. It allows you to travel the crystal-clear waters and immerse yourself in nature's beauty while enjoying the comfort and sophistication of a well-appointed yacht as the captain and the crew take care of the itinerary, navigation, and day-to-day.

However, depending on the group size and your expectations, it’s worth considering the onboard amenities and features of the boat. If you’re looking to entertain guests, having spacious, well-appointed cabins, large decks, and onboard entertainment is important. For family fun, water toys are essential; for romantic getaways, search for yacht charters offering Jacuzzis, SPA treatment rooms, and a personal chef onboard.

Some of those amenities are calculated into the rental price and don’t require extra budget, but it’s always best to speak to your charter broker and search for yachts that will offer the following features:

Large Swimming Deck

Most Caribbean yacht charters offer large, spacious swimming decks so you can easily jump into those turquoise-blue waters. Easy access to the sea opens up opportunities for snorkeling, diving, and swimming.

Jacuzzi Hot Tub

Enjoying a rum cocktail in a hot tub on the deck beneath the starry Caribbean skies is an amazing experience – if you’re looking for a luxurious, romantic feel to your evenings, look for yacht rentals offering a Jacuzzi onboard.

Onboard Fun

If you love staying active and healthy, a private yacht offering an open-air gym, a basketball hoop, or a SPA treatment room might be your best bet.

Water Toys

Jetskis, kayaks, paddleboards, and snorkeling equipment add a touch of adventure to your luxury yacht charter. If you love getting out there and exploring, water toys on your private charter are a must.

Greater Antilles FAQ's

How much is a yacht charter in Puerto Rico?

A yacht charter in Puerto Rico can cost anywhere between $22,000 - $50,000, depending on the season and the type and size of the yacht. Luxury yacht charters in Puerto Rico can cost $50,000 - $150,000 and upward.

Yes, you can rent a yacht in Jamaica. Montego Bay and Ocho Rios are the two popular yacht rental ports in Jamaica.