Greater Antilles Yacht Charter

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Greater Antilles Superyacht Charter

The Greater Antilles are the largest and most storied islands of the Caribbean, a group encompassing Cuba, Jamaica, Hispaniola, Puerto Rico and the Cayman Islands. Rich in culture, history and natural beauty, they offer a vibrant and endlessly varied cruising region at the very heart of the Caribbean Sea.

These great islands are famous for their beautiful coastlines, from long white beaches and clear turquoise water to dramatic mountains and lush tropical interiors. Each has its own distinct character and rhythm, from the colonial cities and music of Cuba to the reggae heartland of Jamaica and the vibrant Spanish heritage of Puerto Rico.

The surrounding waters offer superb swimming, snorkelling and diving among vibrant coral reefs, along with sheltered bays, historic harbours and countless beautiful anchorages. Warm trade winds and clear seas make for wonderful cruising throughout much of the year.

Ashore, the islands offer rich history, celebrated cuisine, and a warmth and vitality that are quintessentially Caribbean, from vibrant music to colourful colonial towns. Their culture and beauty are irresistible.

With their beautiful coastlines, rich culture and vibrant rhythm, the Greater Antilles are the grand heart of the Caribbean. Guests can explore colonial cities, relax on white beaches and enjoy the warmth, music and natural beauty of these great tropical islands.
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The Yachts for charter in Greater Antilles

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A 38 metre RMK Marine explorer with a serene Vincent Van Duysen interior, for ten guests.
RH3

38M

RMK Marine

2003

115000€

Guests

The 46-metre Damen Maaskant Scintilla Maris is a hybrid-electric, Polar Code expedition yacht rebuilt from a North Atlantic trawler, with a characterful Vripack interior, full-beam owner’s cabin and 9,000nm range,
Scintilla Maris

46M

Maaskant

2023

136000€

Guests

A 75.2-metre Admiral motor yacht with an unconventional, asymmetric layout and a glass-fronted sea-level swimming pool.
Kensho

75.2M

Admiral

2022

900000€

Guests

A 2024 Ocean Alexander motor yacht offering ten guests five staterooms, a foredeck jacuzzi, sky lounge, and beach club across Florida and the Bahamas.
A SALT WEAPON

34M

2024

Guests

A 31.78-metre Southern Wind from 2014 with a carbon hull to Farr Yacht Design lines and a Nauta interior, sailing eight guests in four cabins between the Caribbean and the
Farfalla

31M

Southern Wind

2014

70000€

Guests

A 47-metre Christensen 155 rebuilt to the hull and refitted again through 2024, carrying nine crew for twelve guests with a foredeck jacuzzi, an open-air cinema and a wellness programme,
SEA CLASS

47M

Christensen

1997

190000€

Guests

A 37.4-metre Sanlorenzo SD122 refitted in 2023, with Portuguese-style seating and a jacuzzi in the bow, Paola Lenti furniture on deck and a 42-knot Pursuit chase tender, chartering the Bahamas
Away

37M

Sanlorenzo

2009

120000€

Guests

The first hull of Sanlorenzo’s 62Steel series, this 61.5-metre yacht offers loft-like contemporary interiors by Francesco Paszkowski Design.
Lemon Tree

61.5M

Sanlorenzo

2021

485000€

Guests

The 67.3-metre Feadship Vassa (ex-Drizzle) pairs a timeless De Voogt profile with a warm, contemporary RWD interior, an open sundeck gym, three lounge areas and a full-width swim platform, cruising
Vassa

67M

Feadship

2012

595000€

Guests

A 49-metre Christensen refitted in 2024, with an air-conditioned aft deck, an elevator to every deck and a fishing programme built around a 42ft Invincible, chartering the Bahamas and Caribbean
REMEMBER WHEN

49M

Christensen

2011

230000€

Guests

A 75.5m Oceanco superyacht built for active charters, with a vast main salon aquarium, a health-club-style gym and an expedition-ready toy collection.
Wheels

75.5M

Oceanco

2018

790000€

Guests

A characterful 42.98-metre Gulf Craft with an exceptional nine-cabin layout for up to 16 guests, a deck Jacuzzi and generous living spaces, cruising the Mediterranean and Caribbean.
Integrity

42M

Gulf Craft

1977

127000€

Guests

The only Custom Line 140 available for charter, brand-new in 2025, with 21-knot MTU performance, Francesco Paszkowski lines and Ferretti Design interiors built for guests who want the most current
Fifi

42M

Custom Line

2025

225000€

Guests

The Mondomarine flagship, 60 metres of full-aluminium performance superyacht with extraordinary Luca Dini interiors featuring backlit onyx, a Baldi crystal chandelier and an unforgettable cactus garden on the sundeck.
Sarastar

60M

Mondomarine

2017

392000€

Guests

Curated Selection

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Discover Greater Antilles

Where to Cruise
A Greater Antilles yacht charter is shaped by a collection of distinct places, from well-known ports and waterfront towns to quieter anchorages, island escapes and stretches of coastline best approached from the sea. Together, they create a more layered way to charter.
Cuba
Journey to Cuba, the largest Caribbean island, where colonial cities, vintage charm, and unspoilt cays meet warm turquoise seas.
Dominican Republic
Experience the Dominican Republic, where golden beaches, dramatic mountains, and colonial history meet the warm Caribbean.
Jamaica
Welcome to Jamaica, the soulful heart of the Caribbean, where lush mountains, waterfalls, and golden beaches meet reggae rhythm.
Cayman Islands
Uncover the Cayman Islands, a trio of coral isles famed for Seven Mile Beach, Stingray City, and world-class diving.
Puerto Rico
Escape to Puerto Rico, where historic old San Juan, glowing bioluminescent bays, and golden beaches meet the Caribbean.

Highlights

Greater Antilles Yacht Charter
Greater Antilles yacht charters offer the freedom to experience the destination on your own terms. Each itinerary can be shaped around the way you want to travel, with the flexibility to move between time on the water, moments ashore and the simple pleasure of life on board.
Grand Caribbean Islands
Cuba, Jamaica, Hispaniola and Puerto Rico form the core of the group, alongside the smaller Cayman Islands to the west, together making up the largest landmass in the Caribbean Sea. Hispaniola alone is shared between two nations, the Dominican Republic and Haiti, each with a distinct history and culture. Collectively, the Greater Antilles cover more area and hold a larger population than the entire Lesser Antilles chain further east, giving the region a correspondingly wider range of landscapes and cultures to explore.
Beautiful Coastlines
Long white beaches and clear turquoise water line the coasts, backed in places by genuinely dramatic terrain, including Jamaica’s Blue Mountains, which rise to over two thousand metres within sight of the sea, and Cuba’s Sierra Maestra range, close behind at just under two thousand metres in the southeast. This combination of beach and mountain scenery within a short sail is unusual even by Caribbean standards, giving cruising itineraries here more variety than the flatter islands further east.
Rich Culture
Each island has a rich and distinct culture shaped by different colonial histories: Spanish in Cuba and the Dominican Republic, British in Jamaica and the Cayman Islands, and a complex mix of Spanish and American influence in Puerto Rico. Music runs through all of them, from Cuban son and Jamaican reggae to Puerto Rican salsa and bomba, and each island’s cuisine, architecture and rhythm of daily life reflects this same layered heritage in its own distinct way.
Vibrant Reefs
Vibrant coral reefs surround the islands, part of the wider Caribbean reef system that supports some of the region’s best diving. The Cayman Islands are especially renowned, with Grand Cayman’s Stingray City letting guests wade among dozens of resident southern stingrays in waist-deep water, while wall dives drop away into deep blue just offshore. Puerto Rico adds a rarer draw: Vieques’ Mosquito Bay, recognised by Guinness World Records as the brightest bioluminescent bay on earth.
Colonial Cities
Colonial cities and colourful towns dot the islands, none more atmospheric than Havana, where restored eighteenth-century plazas sit alongside faded grandeur and vintage American cars still work as taxis. Marina Hemingway, built in the 1950s and renamed after the Cuban Revolution in tribute to the author, remains the main gateway for private yachts visiting the capital. Santo Domingo’s Zona Colonial, the oldest European settlement in the Americas, and San Juan’s Spanish fortresses add further layers of history.

Greater Antilles Yacht Charter Enquire

Enquire about a Greater Antilles yacht charter to receive current yacht availability, seasonal guidance and expert insight into the cruising areas, anchorages and experiences that best fit your preferred style of charter, creating a clearer route to the right itinerary.

Charter Guide

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Greater Antilles Yacht Charter Itineraries

The Week Unfolds
Across Greater Antilles, each itinerary reveals a different rhythm, from lively ports and waterfront towns to secluded anchorages, island escapes and stretches of coastline best discovered from the sea. Together, they create a more layered way to explore, with every route shaped by the places, experiences and moments found along the way.

Greater Antilles Must See & Do

The anchorages, experiences and places that define a yacht charter in Greater Antilles, and the ones worth building your itinerary around.
Top Anchorages

Marina Hemingway, Havana’s gateway for private yachts
Montego Bay, Jamaica
Samana Bay, Dominican Republic
Fajardo, Puerto Rico’s eastern marina hub
George Town, Grand Cayman

Top Things to Do

Wander Havana’s restored colonial Old Town
Wade with stingrays at Grand Cayman’s Stingray City
Kayak the bioluminescent waters of Vieques’ Mosquito Bay
Watch humpback whales in Samana Bay
Explore San Juan’s Spanish colonial fortresses

Top Places to Visit

Havana, Cuba
Santo Domingo’s Zona Colonial
Montego Bay, Jamaica
San Juan, Puerto Rico
George Town, Grand Cayman

Greater Antilles Charter Guide

Everything you need to know before chartering a yacht in Greater Antilles, from the best time to visit to where to drop anchor.
When's the best time to charter the Greater Antilles?

December through April is the most reliable window, falling within the Caribbean dry season and outside Atlantic hurricane season, which officially runs from June through November and peaks between August and October. Winter also brings the most comfortable temperatures and the calmest crossing conditions between islands. Guests wanting to combine a charter with whale watching in Samana Bay, Dominican Republic, should aim for January through March, when humpback whales gather there to breed.

How do we get to the islands of the Greater Antilles?

Access varies by island: Havana is served by Jose Marti International Airport, Montego Bay and Kingston by Jamaica’s two main international airports, Santo Domingo and Punta Cana by the Dominican Republic’s several hubs, San Juan by Luis Munoz Marin International in Puerto Rico, and Grand Cayman by Owen Roberts International. Most itineraries are built around one or two islands rather than the whole region, given the sailing distances and separate customs clearances involved.

Which are the best anchorages across the Greater Antilles?

Marina Hemingway remains the main hub for private yachts visiting Havana, while Montego Bay and Ocho Rios serve Jamaica’s northern coast. Samana Bay, sheltered on the Dominican Republic’s northeast coast, doubles as a prime whale-watching anchorage in season, and Fajardo, on Puerto Rico’s eastern tip, gives easy access to Vieques and Culebra. George Town, Grand Cayman, combines a protected anchorage with some of the region’s best reef diving close by.

How many days should we plan for a Greater Antilles charter?

Each island rewards at least five to seven days on its own, given the distances involved. Jamaica or the Cayman Islands suit a focused week-long charter, while combining two islands, such as Puerto Rico with the Dominican Republic, or the Cayman Islands with Cuba, is better suited to ten days or more once transit time and separate port clearances are factored in.

Are there any special considerations for chartering in Cuba?

Cuba’s clearance procedures and the rules governing which vessels and nationalities may visit have shifted several times in recent years and differ depending on a yacht’s flag state and the guests’ nationality. US-flagged vessels and US citizens in particular face specific federal restrictions that change periodically. Given this, it is worth confirming the current requirements with an experienced local agent well before finalising a Cuba-inclusive itinerary, rather than relying on older information.

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