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Cuba Yacht Charter

A Cuba yacht charter is perfect for those who love island hopping. Because, with over 4,000 cays and islets to explore, the Cuban archipelago is the dream Caribbean sailing vacation.

What’s on this page


  • Colorful historic architecture
  • Old town Havana
  • World-famous local rums

Sailing Cuba

Cuba indigens beach selling

Cuba, the most westerly island of the Greater Antilles, sits between the Caribbean Sea and the Atlantic Ocean, just 90 miles from Key West in Florida. From mountains to coral atolls with white sandy beaches, the natural beauty of Cuba has to be seen to be believed. As does the colorful architecture of the island’s historic cities.     

With a favorably warm climate and steady winds, Cuba yacht charters have always been popular among sailors. Even more so now that the country has a reliable marine infrastructure, with around 20 marinas and nautical centers that offer a range of services and welcome yachts under all flags.

From our base at Punta Gorda in Cienfuegos, you can explore the gorgeous Cuban coast, its many cays and the idyllic Archipelago de los Canarreos, which is within easy reach.   

On your Cuba yacht charter, the cities of Trinidad and the capital, Havana, are not to be missed. At either of these UNESCO World Heritage Sites, why not learn to rumba or salsa, or take a ride in a retro American classic car? And you shouldn’t leave before sampling the famous Havana Club rum

Available charter types


For experienced sailors, a bareboat charter is the perfect getaway.


Relax and leave all the sailing to a professional skipper.

Easy crewed

The simplest, hassle-free way to charter a crewed private yacht.

Fully crewed

Your own private yacht for an all-inclusive luxury sailing vacation.

Cabin cruise

Reserve a private ensuite stateroom on a modern catamaran.


Low package rates for island-hopping aboard a sailing yacht.


Get closer to nature on the perfect self-catering Caribbean vacation.

Power Catamaran

Cruise faster and see more on the perfect charter boat.

Things to do in Cuba

Cuba relaxed girl in yacht charter

Explore Cuba’s capital

Havana is the capital and soul of the country, so make sure you put a visit at the top of your list of things to do in Cuba. Wander the cobblestone streets of Old Havana and admire the unique blend of baroque and Spanish colonial architecture. See the vintage fleets of cars, enjoy the nightlife and visit the hippest district of Vedado.

Taste an authentic mojito

This well-known cocktail was invented at La Bodeguita del Medio, a small bar in Old Havana where the walls feature photographs of famous celebrities with their mojitos. This will taste a world away from other mojitos you’ve had before and is well worth a try during your Cuba yacht charter.

Try Cuban salsa dancing

The Cuban beat is infectious and you can’t leave the island without learning a few expressive salsa steps, a dance originating from Cuban folk dances. There are plenty of schools, or you can just join in the dancing at a local bar.

Tour the city of Trinidad

Wander this beautiful colonial city and get lost in its narrow streets, listen to street musicians in the main square and taste the local Canchánchara rum cocktail.

Drop in on the Sea Turtle Hatchery

One of our favorite things to do in Cuba is to pay a visit to the Sea Turtle Hatchery in Cayo Largo, which makes for an unforgettable experience. At certain times of the year, you may even witness the release of baby turtles. Afterwards, head to Sirena and Paraiso beaches for wonderful sands and turquoise water.

Enjoy the wildlife

Visit Cayo Rico with its established colony of Cuban Rock iguanas, or sail to the mooring buoys of Hijos de los Ballenatos, put on your snorkel and explore a rich underwater world full of marine life.

Weather insights

Cuba wildlife beach iguana

When is the best time to visit Cuba?

The best time to visit Cuba is when the climate is relatively dry and cooler, from late November to mid-April. 

The year-round climate is subtropical to tropical and fairly uniform from one area to the next. The average temperature in Cuba is around 77ºF between November and May, reaching 82ºF between December and February in the south. Short bursts of rain can bring temperature lows, particularly in the northwest. 

The rainy season is from late April to early November when temperatures are warmer (around 91ºF) and the humidity is high.

What are the sailing conditions in Cuba?

The sailing conditions in Cuba feature winds predominantly from the northeast, ranging from 5 to 35 knots depending on the time of year. Typically, winds are northeasterly between 15 to 25 knots but can be highly variable depending on the tropical depressions in the Gulf of Mexico and Bahamas. 

We recommend the use of the paper charts, Geocuba, as electronic charts are not accurate enough.

Cuba kayak activity fun vacation beach

Sailing Cuba with Dream Yacht Charter

Cuba yacht charter

Sail Cuba, take the helm and plan your dream vacation itinerary. Snorkel vibrant coral reefs and relax on the perfect catamaran or monohull.

Skippered charters Cuba

You can enjoy sailing Cuba even if you don’t have any sailing experience. Just hire a skipper and they will sail you and your guests around Cuba’s highlights.

Cuba by the cabin charters

Relax and experience Cuba without any hassle. Reserve a stateroom and private bathroom, while our crew take care of the planning, sailing and full-board cooking.

Cuba crewed charters

Enjoy a luxury, all-inclusive sailing vacation in Cuba with discreet five-star service. Hire our private yachts with crew and tailor the menu and itinerary to suit your preferences.

Cuba catamaran charter

Cuba sailing itinerary

Take a look at our Cuba sailing vacation suggestions

Cuba local streets old town tourism 7-day itinerary Cuba

Day 1

Explore Cienfuegos with its striking and brightly-colored French colonial architecture flanked by palm trees, wide streets with covered sidewalks and a vibrant waterfront. Head to Parque Jose Marti, a large square home to great street food, shops, free Wi-Fi and a bandstand. Walk Punta Gorda, dine at the nearby restaurants and watch the sunset. Take a taxi for an hour further inland to the El Nicho waterfalls, where you can swim in the less busy lower pool. As you head to Guano del Este, keep a look out for Jagua Castle at the entrance to the bay and dolphins. Guano del Este features a strange-looking lighthouse and sandy beaches with coral in shallow waters.

Day 2

Spend the day at Cayo Largo, a small limestone cay which was popular with pirates wanting to hide their treasure. You can anchor off Playa Sirena, which is a fabulous beach fringed with palm trees and amazing snorkeling, although the waves are invigorating. Make sure your camera is ready, as photos taken here will be the envy of all with its glittering turquoise waters and plenty of soft white sandy beaches to choose from. Try Playa Paraiso, which was rated by TripAdvisor as one of the top 25 beaches in the world, or, if you want seclusion, head west of Sol Cayo Largo.

Day 3

Spend the day exploring Cayo Largo in the morning. Animal lovers can visit the Sea Turtle Hatchery, Centro de Rescate de Tortugas Marinas, which is part of a major conversation program. Keep watch for the resident iguanas too. After lunch head to Quinto Canal, about 30 minutes away, where you can bathe in a natural pool off a sandbank that is calm and warm. Sail onwards 40 minutes to the Cayos Los Ballenatos coral reef, which is great for snorkeling and has vibrant underwater marine life. You’ll spot plenty of tropical fish and perhaps even sea turtles. You can head back to Quinto Canal or Cayo Largo overnight.

Day 4

After breakfast make for Cayo Rosario, an uninhabited island except for a healthy population of iguanas. This is a popular diving and snorkeling location because of the richness and variety of fish and sea creatures. If you want to relax on the beach, you’ll find a stunning, large stretch of pink sand that wraps the lower part of the cay. You can spend hours looking at the shells and beachcombing.

Day 5

Set sail for Cayo Estopa and enjoy the beach, lazy swimming and snorkeling. In the afternoon, sail to Cayo Rico with its light pink sands, healthy coral and fantastic shoals of tropical fish – you might even see large starfish and rays. This is a wild island with just one small seafood restaurant near the jetty, which is popular and reasonably priced if you want fresh lobster. As you relax on the beach, you can watch the iguanas scuttling around and they love eating fruit.

Day 6

Head back to Cayo Largo to relax on one of the many beaches. Dine at the beach grills (ranchóns) at lunch time where you can order shrimp and lobster. You can also find a la carte restaurants, which are open in high season. If you are there on a Friday, you can take part in the weekly fiesta for a small fee. Sail onwards to Cayo Sal and explore the cay.

Day 7

Head back to Cienfuegos before 10am to disembark. Don’t forget to get back in touch and book your next Dream Yacht Charter.

Useful information for Cuba yacht charters

Cuba wildlife dolphins

How do I get to Cuba from the US?

You can fly direct to Cuba’s José Martí International Airport (HAV) from many eastern US cities.

What language is spoken in Cuba?

The language spoken in Cuba is Spanish.

What is the currency for Cuba?

Cuba has a dual currency system where locals use the Cuban Peso and visitors use the Cuban Convertible Peso (CUC). American Express, along with credit and debit cards belonging to US banks are not accepted. So make sure you bring enough cash to cover time spent on your Cuba yacht charter.

What are the customs restrictions for Cuba?

You need to clear with the authorities whenever you enter or exit a port. The boat’s papers must be shown, as must the passports and visas of all crew. Clearance is free of charge and mandatory.

What documents do I need to sail Cuba?

To visit Cuba you will need a US passport that is valid for the duration of your stay. There are some travel restrictions for US citizens wanting to visit Cuba, but they are easily manageable. 

You will also need a tourist card, available from the Cuban consulate, and non-US medical insurance, which you can buy from the airport on arrival in Cuba.

Talk to us to make sure you have the correct documents before you travel.

How do I get around Cuba?

Getting around Cuba is easy if you use the government-run bus routes. The local buses are cheap but popular, so buy your tickets the day before. Renting a car is expensive and difficult so book ahead. You can also rent a taxi from among Cuba’s fleet of vintage cars, which is an experience in itself.

What is the Wi-Fi like in Cuba?

Wi-Fi is not available on board our yachts or in our marina. There is internet access via Wi-Fi hotspots, but you need a pre-paid NAUTA internet Wi-Fi card. All international marinas in Cuba have Wi-Fi hotspots. Verizon has a roaming agreement in Cuba, but don’t forget the roaming fees.

What regulations are there in Cuba?

Night sailing is absolutely forbidden by Cuban authorities due to the difficulty of navigating coral reefs, floating objects, private fishing boats, etc. Fishing with a harpoon and lobster fishing are also forbidden.

Navigation is only permitted in national waters. After leaving our marina, anchoring is prohibited all along the coast near Cienfuegos and within the bay. You can anchor to the east, from the Casilda area and westward from Cayo Guano del Este. You must respect the forbidden zone, the Bay of Pigs, that is southwest of Cienfuegos.

There are strict regulations prohibiting bringing satellite phones, drones, GPS or DVD players into Cuba. Make sure you are fully aware of all of these restrictions ahead of your Cuba charter vacation.

Where can I find weather forecasts in Cuba?

As internet access can be patchy, most marinas will provide a print out of the weather forecast for Cuba from Windfinder. The Cuban Institute of Meteorology also provides forecasts.

Upon arrival you can monitor the weather and sailing conditions on Channels VHF 16 and 09 in Cayo Largo, Trinidad and Santiago de Cuba marinas.

What provisioning is there in Cuba?

There are plenty of choices for provisioning in Cuba. Please refer to the base guide.

What baggage can I take on my Cuba sailing vacation?

Please only take soft bags on your Cuba yacht charter as suitcases are too cumbersome on board.

What is the electrical current in Cuba?

The electrical current in Cuba is 220V.

What is the dialing code for Cuba?

The dialing code for Cuba is +53.

Why should I book with Dream Yacht?

Dream Yacht Worldwide is now the world’s leading yacht charter company and offers you:

  • A diverse fleet of yachts with a wide variety of models and manufacturers to suit every type of sailor.
  • We have +60 exciting destinations and we’re a pioneer in finding new sailing grounds.
  • You can be assured of our commitment to customer service excellence.
  • You’ll receive a warm and friendly welcome from our base teams who will share regional tips, recommendations and advice.
  • We’re also a trusted seller of new and used boats and an innovator in charter management options – sailing is our business.

What licenses do I need to hire a yacht and sail myself?

The skipper of a yacht has primary responsibility for the safety of the crew and yacht at all times. Many destinations require just relevant experience demonstrated by a sailing resume.

To charter in the Mediterranean, it is mandatory that you hold a sailing license recognized by the local port authorities for bareboat charters in Italy, Greece, Croatia, Spain, Malta, Montenegro and Turkey. Other destinations that require a license include Madagascar, Seychelles, Thailand, Brazil and Sweden. For Belize, the port authority will issue a certificate of competency and an application is made on arrival.

You must take your proof of competency and original certificate with you on your charter. We advise you to contact our team about your qualifications and destination requirements before booking.

By accepting the yacht contract you are confirming that you and/or members of your crew are capable and competent to sail the yacht in the conditions and cruising area of the charter. We reserve the right not to hand over the yacht if, after inspection, it is the opinion that the charterer is not, or may not be competent to be in charge of the vessel.

What is a skippered yacht charter?

A skippered yacht charter is when you rent one of our boats for you and your guests and a professional skipper sails it for you. No sailing experience is needed.

You will need to choose a yacht with a cabin for your skipper to sleep in as they are responsible for your yacht for the duration of your charter. We will find the skipper for you once you have found your perfect destination and yacht.

You will need to pay for your skipper’s food. You can invite the skipper to dine with you on board or out at a local restaurant.

What is the difference between crewed and by the cabin charters?

Our by the cabin charter charters offer exciting destination tours on a set itinerary crafted by our destination experts. You can book a double cabin and private bathroom and will share the boat with other guests who have booked the other available cabins. You will be looked after by a professional skipper and hostess with itineraries ranging from three to 11 nights. There is a set menu and included meals and drinks vary depending on location.

Can you tell me about your yachts?

Our super premier yachts are less than 12 months old from their first charter date, while premier yachts are less than three years old from their first charter date. Our yachts are well maintained and undergo regular, scheduled technical inspection.

In case of emergency, you can rely on our hotline, at any time, seven days a week. If you experience a technical failure affecting major and important parts of the yacht, we will repair the failure within four hours of receiving your call during working hours (8am to 5pm). If you lose more than four hours (during working hours), we will compensate you for one full day. If the repair takes more than one day, we will provide you with a similar boat or compensate you on a pro-rata basis. If restrictions to this guarantee apply in specific areas, this will be detailed during the charter check-in at the base.

Do I need insurance?

We highly recommend you arrange travel insurance in case you need to cancel for an unexpected reason to cover non-refundable deposits. Please make sure you have personal travel insurance that covers sailing.

We will insure the vessel throughout the charter with first-class insurers against all risks, to provide permission to charter as under contract terms and to cover third-party liability.

The following options are available in limited locations:

  • Security Deposit: This varies on the size of the boat and when the boat is returned without damage it is refunded.
  • Damage Waiver: The charterer agrees to pay a non-refundable damage waiver at the time of booking, as well as a reduced damage deposit on embarkation that is refundable upon completion of the charter should no damage occur.

Ever considered a Cabin Cruise?

As pioneers in the industry, Dream Yacht was one of the first to develop the Cabin Cruise concept. It’s an ideal choice for solo or couples travelers seeking relaxed adventure, exotic destinations, and unique local cultures in an intimate, social setting – in comfort at sea.

Our promise

Private accommodations

Comfortable and private standard double cabins with ensuite bathroom

Curated itineraries

Experience world-class destinations, local culture and excursions with our expertly curated itineraries


An affordable and intimate experience without the need to book an entire yacht or provide sailing qualifications

Vetted crew

Enjoy our professional crew with a strong local knowledge and friendly service

Full board meals

Enjoy fresh and delicious cuisine prepared and served daily

Choose your mood

Relax on deck socializing with fellow travelers, kayak or snorkel from your yacht, or enjoy exploring ashore

Get inspired! #MyDreamYacht

Follow our customer’s journeys & then get ready to share your own amazing experiences on Instagram

Simply wonderful! Fred + Isabelle were so accommodating and did so much for us. Isabelle’s food was incredible. Thank you so much!


Exumas Cabin

Great class. Very professional and great service!


Antigua Bareboat

Just what we needed to get out of a year of lockdown, see new places and connect with nature. Highly recommended for your next sailing adventure!


St. Martin Bareboat

Excellent cruise and wonderful stay on board. Skipper attentive, very pleasant and very professional.


Guadeloupe Skippered

I have just returned from another fantastic week of sailing at your base in Pula and would like to thank everyone involved for making this possible at such short notice and without any problems.


Guadeloupe Bareboat

The marina itself is a perfect base with super facilities! The Lagoon 42 was in good condition and the skipper was fantastic and knew the area very well.


Croatia Skippered

What an EXCELLENT experience. We just returned from a week long charter with skipper from Corfu, sailing around the beautiful islands of the Ionian Sea. Paxos, Antipaxos and the old town of Corfu were beautiful and the secluded bays we got to visit thanks to our local skipper Nicholas were simply stunning. Fly and Flops was yesterday – we will only charter with Dream Yacht for the foreseeable future.


Greece Skippered

Our group of 10 had a WONDERFUL time in French Polynesia from May 21-28, 2022! The food was fantastic: captain and cook, husband and wife: Henry and Mehee (sp) were amazing and the whole experience on board was a dream! We can’t wait to book another trip through Dream Yacht


Tahiti Crewed Premium

Dream Yacht provided a great sailing experience for my extended family on 2 monohulls from Scrub Island. The boats were in very good condition and perfectly prepared, the staff friendly and helpful. I had worked for a number of charter companies over the years but Dream Yacht is one of the


British Virgin Islands Bareboat

I am in the Maldives right now and having the time of my life. Captain Jack and the crew are professional, safe and fun! The boat is optimal and the food is delicious. The chef even bakes CAKE! The beds are surprisingly comfortable and we sleep 9 hours every night. If you like island hopping, there is no better option than Dream Yacht. We will be booking Tahiti next year.


Maldives Cabin

The new boat was in perfect condition and best condition for exploring bays and islands. I could never have imagined that this could be so much fun and enjoyable and we are already looking forward to the next upcoming trip in the Ionian


Scandinavia Bareboat

Baja is now my favorite place. There was something for everyone: sailing under northerly winds with mostly calm evenings, snorkeling, fishing, secluded sandy beaches, pelican feedings, being greeted by barking sea lions, and exploring the geology of Ispiritu Santo Island. Dream Yacht Base La Paz provided competent professional support with a well-equipped and maintained boat. We were wonderfully cooked by an on-board chef arranged with Dream Yacht, which meant more free time for all of us. An unforgettable vacation and adventure connected with nature.


Mexico Crewed Premium

All the staff were fantastic and made our trip a memorable one. Incredibly friendly and welcoming, the food was fantastic. The service throughout the trip was always top notch!


Thailand Cabin

Absolutely recommendable. Perfect service. Will charter again and recommend Dream Yacht Charter anytime.


Turkey Bareboat

I just returned from 3 weeks of fantastic sailing with my family on one of your catamarans in Sardinia. My thanks to our skipper Simone and Daniela, our cook.


Sardinia Skippered

For a first cruise as a skipper, the Mediterranean is perfect. The service of Dream Yacht is too!


France Bareboat

We had an incredible trip and got engaged on our very first night of sailing! We will surely come back one day. We were beginners, we were guided very well and that gave us a lot of confidence.


Australia Bareboat

The experience on board far exceeded our expectations. Isabelle provided exceptional three course meals. Her creativity and delicious meals were incredible. Thomas was an excellent skipper, he “felt” our needs. Thanks guys!” Spira, bareboat with crew in New Caledonia.


New Caledonia Crewed Premium

Once again a fantastic sail with a great crew. Thanks again to a great captain and cook. Was totally fantastic.


Seychelles Cabin

A very excellent sailing vacation – especially the crew was fantastic. I would sail with Dream Yacht again and highly recommend them.


Guadeloupe Bareboat

I loved the vacation and am not sure this trip can ever be topped. Everything about it was incredible. The captain and crew were great, helpful, friendly, attentive and knowledgeable. We loved it.


Greece Crewed Premium

We just returned from one of your Lagoon 52F’s last week in St. Thomas! We had the trip of a lifetime sailing around St. Thomas and St. John!


US Virgin Islands Bareboat

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