Luxury Yacht Rental in the Greater Antilles

Luxury Yacht Charter Guide to the Greater Antilles

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. Spend late nights dancing and throwing back rum in Old Havana before heading east to snorkel in the worlds largest coral reef fringing the shores of Cuba. Head to Puerto Rico for some R&R with its sugar beaches, lost islands, and luminescent waters, for those seeking havens far from the madding crowd, the Greater Antilles is your golden ticket.

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

Cultural Flair

Puerto Rico is where Spanish flair meets Caribbean charm, and the melding of these two cultures comes together wonderfully. From the heady scent of 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, make no mistake. 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.

Beautiful Beaches

A vision of vivid perfection; the beaches of Puerto Rico sure to capture that Caribbean charm – with an added edge. 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 precolonial ruins curate a fascinating picture of settlers, swashbucklers, and smugglers in Puerto Rico. If you leave your yacht charter behind for just one trip over in Cuba – be sure to make it 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 Jurrassic period. This is a great place to go horse-riding especially if you want to see the sprawl of tobacco and coffee plantations

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


Home of painted grand avenues, crumbling squares, classic cars and a whirlwind of sights and sounds -Havana is more likely to knock you off your feet, than to sweep you away. Still, Cuba’s capital 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 tout – but don’t leave the city without a ride in a classic car.

San Juan

Down in Old San Juan, luxury yacht charter guests will find one of the most strikingly well-preserved examples of Spanish colonial architecture. The town is a welcome humming medley of cobblestone streets, pretty painted facades, and looming fortifications. 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 take dinner at one of the Michelin star spots For the edgier traveler - a street graffiti tour and evening of island invented Pina Coladas could be an alternative menu.

Cayo Largo

The once upon a time pirate base of Cayo Largo is a sight for sore eyes. One glance at the gorgeous white sands and turquoise waters and you understand exactly what yacht charter days are made of. This stretch of Caribbean purity is all about embracing the art of watersports. Spend days sizzling crab suppers on the beach, kayaking along the scenic coastline, and diving into the serene depths to discover tropical delights. Curious travelers can also take the tender up to the northern tip to neighboring Cayo Iguana where hundreds of prehistoric iguanas can be found wandering around.

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 and late spring and early summer are swell times to visit if you are seeking warm weather and lazy beach days.

Yachts by type

Motor yachtsSailing yachts