Havana cityscape at sunset with El Capitolio dome, historic buildings, and waterfront.
YACHT CHARTER DESTINATION

Cuba Yacht Charter

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Cuba: A Time Capsule Wrapped in Caribbean Blue

Cuba is one of the most culturally rich yacht charter destinations in the Caribbean, offering a rare mix of vibrant history, untouched nature, and world class diving along more than 289 natural beaches. Just 90 miles from Key West, Cuba blends the Caribbean Sea, the Gulf of Mexico, and the Atlantic into one uniquely diverse cruising ground.

Start in Havana, where fading colonial architecture, classic cars, and legendary spots like the Tropicana Club and Hemingway's old haunts set the tone for the trip. From Marina Hemingway, head west to the tobacco fields of the Viñales Valley and the pine covered peaks of the Sierra de los Órganos, then push on toward María la Gorda, where coral heads sit just off the bow and the Lost Paradise wall dive draws serious divers. Continue east to the quiet island of Cayo Largo, once rumored to be a pirate hideout and now home to some of the clearest water and finest beaches in the country.

Part history lesson, part beach escape, and part diving adventure, a Cuba yacht charter feels unlike anywhere else in the Caribbean.

Charter Itinerary

For a full itinerary, or to build your own experience, please inquire.

Aerial view of a long peninsula with white sand beach, turquoise water, and a coastal town.

DAY 1

Havana

Meet your yacht at Marina Hemingway, named after, Ernest Hemingway, who loved Cuba and lived on the island for many years. The marina is just a 30-minute drive from downtown Havana, where you can wander the streets, taking in the curious contradiction of its fading colonial architecture and vibrant culture. That night, arrive at the legendary. Tropicana club in a vintage car and enjoy Latin music, dancing and plenty of Cuban rum.

A vibrant Havana street scene with a large Cuban flag overhead and classic cars.

DAY 2

Havana

Spend another day in this fascinating city and visit Papa Hemingway’s favorite drinking haunts of El Floridita and La Bodeguita del Medio. Take a short drive out of town and you can visit a cigar factory, where the manager reads the day’s newspapers to his workers as they roll cigars – a beautiful tradition.

Farmer in a straw hat inspecting green plants in a field during a golden sunset.

DAY 3

Rural Cuba

Head west from Havana to discover the tobacco plantations of the Viñales valley and the pine forest covered mountains of the Sierra de los Órganos. It’s a beautiful, slow-paced corner of rural Cuba, a wonderful contrast to Havana.

Two palm trees frame a white sand beach with turquoise water and a distant sailboat.

DAY 4

Maria La Gorda

The yacht will cruise onwards to the beautiful María la Gorda and anchor it the crystal clear waters where the coral heads are just off the bow. This is the place for guests to jump in the water and enjoy fantastic snorkeling, or scuba divers can visit Lost Paradise – a vibrant wall dive with a variety of swim-throughs and caves.

Sailboat on blue water alongside a green island with a coastal village in sunlight.

DAY 5

Cayo Largo

Continuing east, guests can enjoy the tranquility of the small island of Cayo Largo, which is thought to have once been used as a base for the real pirates of the Caribbean. With clear waters and pristine beaches, it is the perfect place to make the most of your yacht’s extensive collection of water toys. Enjoy dinner on board, likely you’ll be the only yacht in the harbor.

School of yellow-finned fish swimming around a large coral formation in clear blue water.

DAY 6

Jardines de la Reina

Sail back into Turkey and the first stop is Marmaris. Drop anchor in its tree-lined bay after a long afternoon of water-sports before heading ashore for a spot of shopping at the bazaar and a drink along the waterfront.

Large white cathedral with twin domes, yellow taxis, and city buildings under sunny sky.

DAY 7

Santiago de Cuba

Return to city life with the bustle of Santiago de Cuba, which is known for its Afro-Cuban influences and colonial architecture. A fleet of classic cars will provide a memorable drive to the airport. Reluctantly make your way back to the modern world, with glorious memories – and maybe a few Cuban cigars, too.

Yachts for Charter in Cuba

VOYAGE 590e
VOYAGE 590e

59’ VOYAGE yacht|2022

12 Guests 6 Staterooms

Caribbean Virgin Islands (US/BVI)

Three smiling women stand behind a counter at an outdoor event with boats.

Ready to start your charter adventure?

Get in touch with us and one of our dedicated charter specialists will be at your service to answer all of your questions.

Frequently Asked Questions

Can US citizens charter a yacht in Cuba?

Yes, but US citizens must travel under the "Support for the Cuban People" category, and additional travel requirements may apply depending on citizenship.

Is Cuba a good destination for diving?

Yes, Cuba offers exceptional diving, including the Lost Paradise wall dive near María la Gorda, known for its swim throughs and caves.

Do you need a visa to charter a yacht in Cuba?

Yes, most non-exempt nationalities require a tourist visa, which can typically be obtained through a Cuban embassy, consulate, or online platform.

What is the Tropicana Club in Havana?

The Tropicana Club is a legendary open air cabaret in Havana known for its elaborate performances, live music, and vintage Cuban glamor.

What is the best time of year for a Cuba yacht charter?

The dry season, from November to April, is the best time for a Cuba yacht charter, offering consistent trade winds and warm, pleasant weather.