Cuba Sailing Holiday


On Request


Cuba Sailing Holiday

Begin with a private comprehensive tour of Havana. Santa Clara in central Cuba, is the city of Che Guevara. At its heart is the central Parque Leoncio Vidal, ringed with architecturally beautiful buildings including Teatro La Caridad, the 19th-century, colonial style theatre. Trinidad, on the Central Coast, facing the Caribbean Sea is characterized by brightly coloured Spanish colonial buildings. Beach on Playa Ancón, hike to Javira Waterfall or climb the tower of La Iglesia y Convento de San Francisco in central town. 

In Trinidad, charter a luxury yacht, take your rum and set out to sea, Hemingway style. Cruise the Caribbean tropical waters to Cayo Blanco de Casilda, where an open restaurant (Ranchon) on the beach serves seafood dishes and cocktails. Sail for Cayo Macho de Afuera with several beaches and coral reefs. At Cayo Zaza de Fuera, throw a line and trawl for fish. And as the bell-tolls, settle down for an evening meal of lobsters. 

And, experience Havana, Santa Clara & the colonial city of Trinidad.

What We Love
  • Visit Santa Clara, with a fine colonial centre, well-restored mansions, theatres and churches 
  • Explore Trinidad, the Spanish colonial city with its grand buildings and architecture.
  • Spend some quality time on a private yacht with your own skipper and cook.
  • Travel any day – shorten or lengthen the tour to suite your wishes.
  • This tour is designed to provide maximum outdoor experience.
What to Know
  • This is a relaxed tour but may require walking on rough surfaces.  
  • We carefully select the world's best boutique tour companies in each destination.
  • We offer 24/7 support to give you complete peace of mind during your holiday.
  • We strongly recommend that you take travel insurance for this holiday.


Cuba goes beyond all sailors' dreams - a favourable, warm climate year-round, steady winds, unique natural beauty and open-minded hospitable people contribute to this as well as the reliable nautical infrastructure, which is receiving well-aimed promotion and extension by the Cuban government.

The magic of the largest island of the Antilles is the combination of nature, climate and its people. Beautiful landscapes as well as seascapes make Cuba the ideal setting for tropical holidays throughout the year where nautical adventures and activities are at there best, with the local charismatic and hospitable multi-cultural population welcoming the visitor to the country.

There are some 200 bays and 289 natural beaches with crystal clear navigable waters all year round and an annual average temperature of 25º C as well as the varied marine flora and fauna that Cuba has to offer, visitors come to enjoy Cuba’s unique Caribbean appeal that makes this island the ideal destination.

All-inclusive Sailing Adventure: Board your exclusive yacht in Trinidad, from the yacht marina base situated on the southern Caribbean shore of Cuba. Trinidad is a UNESCO World Heritage site and one of Cuba’s oldest Spanish colonial cities. The city is steeped in history, and is situated below the Escambray Mountains and the Topes de Collantes National Park. It is filled with entertainment and eateries; the city is a hub of activity for nightlife or just soaking up the Cuban culture.

The Jardines del la Reina (Gardens of the Queens) is a ‘lost paradise’ where you will visit deserted cays with pristine white sandy beaches and rare exotic wildlife. It is an excellent yachting location with clear waters and azure lagoons, especially excellent for exploring marine life through snorkelling or scuba diving.

In the safe hands of an experienced yacht skipper with local knowledge and with a deckhand/cook, you can assist in sailing the yacht and use your culinary skills to help prepare the onboard meals or barbecues on the beaches. Lobsters, tropical fruit, rum and Havana cigars are some of the things to enjoy.

Getting There

Virgin Atlantic is the only airline operating direct scheduled flights to Cuba, with two services a week from Gatwick.

Various airlines fly to Havana from London via European cities, including Madrid, Paris, Amsterdam and Rome. Air France is the most versatile option, with daily flights from London Heathrow to Havana via Paris. Iberia and KLM also fly from Heathrow, via Madrid and Amsterdam respectively. Other airlines flying direct from European cities include Cubana, KLM, Air Berlin and Air Europa. Though Cubana tends to offer the least expensive flights on the market, they have a justified reputation for overbooking, overzealous enforcement of the baggage weight limit.

Cuba Sailing Holiday Cuba

Cuba Sailing Holiday

Havana, Santa Clara, Trinidad & Yachting
(10 Days – Travel Any Day)

Day 1 – Arrival
Havana Meet and greet on arrival at Havana Airport and (40 minute) transfer to colonial hotel in Old Havana for your 4-night stay. Welcome Cuban cocktail. Relax and enjoy some free time before exploring the town in the evening.
Overnight in Havana

Day 2 – City Tour
Havana This morning, with your private guide and driver, enjoy a tour of a famous cigar factory to see the process of hand-rolled cigars followed by a visit to the Capitolio building. Afterwards travel by horse drawn carriage along the Prado to the Arms Square for a guided walking tour of colonial Havana. This afternoon and evening is free for you to explore Havana.
Overnight in Havana (B, D)

Day 3 – Transfer
Santa Clara Take a private transfer to the airport for your flight to Santa Clara City. Meet and greet on arrival and transfer to the Los Caneyes hotel, featuring aboriginal bamboo construction. If time permits, we'll tour the city including Vidal Park, La Caridad provincial library and more. We'll also visit the Ché Guevara Memorial, housing his tomb and museum.
Overnight at Los Caneyes hotel (B, D)

Day 4 – Transfer
Trinidad With your private guide and driver travel to the Escambray Mountains past lush countryside and a small natural waterfall to the summit. At the top, visit the former hospital transformed into a hotel/health spa, 780 m above sea level. Packed lunch will be provided after a hike to a waterfall, where you can take a refreshing swim before transfer to Trinidad, a UNESCO World Heritage Site.
Overnight at Las Cuevas hotel overlooking (B, L, D)

Day 5 – Cruise
Cayo Blanco de Casilda Embark a luxury yacht and meet yacht skipper for a briefing. Depart yacht berth for day cruise through the Caribbean tropical waters to Cayo Blanco de Casilda, where an open restaurant (Ranchon) on the beach serves delicious seafood dishes and local cocktails.

After lunch, observe the iguanas in their natural environment or enjoy snorkelling in the coral reef. Overnight on Yacht (L, D)

Day 6 – Cruise
Cayo Macho de Afuera Today we will sail for Cayo Macho de Afuera. The cay has several beaches and coral reefs, iguanas and jutias. As the sun goes down under the yard arm we have an aperitif and dinner under the stars.
Overnight on Yacht (B, L, D)

Day 7 – Cruise
Cayo Zaza de Fuera After a hearty breakfast all hands on deck, hoist the main sail and reach out for Cayo Zaza de Fuera. Take your turn at the helm and steer the yacht to the south east. Try your hand at navigating and see if you can plot a course to your next waypoint. Throw a line and trawl for fish. Lobsters are numerous enough to be your daily diet. Treasures from old day pirates are said to be scattered on the seafloor and hidden on the cays. As the bell-tolls, settle down for an evening meal.
Overnight on Yacht (B, L, D)

Day 8 – Cruise
Trinidad A leisurely sail in the Caribbean trade winds and sunbathing on deck or the trampoline as we make way to Trinidad where we have a ‘All hands on deck’ party and lashings of rum served by your Captain. Here you can discover the best-preserved historic city of Cuba, restored to its 16th century apparel and ranked World Heritage Site by the UNESCO. (B, L)

Day 9 – Transfer
Havana Enjoy the Special Hemingway Trail city tour of Havana visiting the Ambos Mundos Hotel to see the room where Hemingway stayed and wrote some of his works. Go onto the bar, La Bodeguita that he frequented to enjoy his Mojito cocktail and his favourite Cuban food, and then to the El Floridita where he developed the now famous Daiquiri, which you can also enjoy. We travel to his house at La Vigia Farm and onto Cojimar where we have lunch at the restaurant that he frequented. Tonight enjoy cabaret & dinner at Havana Café.
Overnight at hotel in Havana (B, L, D)

Day 10 – Depart
Havana Spend the day at your leisure before your transfer to Havana International Airport for outbound flight. (B)


Make this your holiday

  • Exclusive Tour: your own private multilingual guide throughout the trip  
  • Price Guarantee: costing 25-30% less than similar tours of the same flexibility and quality
  • Tailor Made: customised itinerary to create your dream holiday
  • Duration: shorten or lengthen the tour to suit your wishes
  • Dates: depart and return whenever you choose
  • Hotels: change hotel grade to suit your budget
  • Group Discounts: call 020 8350 6199

When to go Cuba is an all year round destination and there isn't a bad time to visit Cuba. It has primarily a tropical climate where temperature rarely falls below 27 degrees C (81 F) and reaches a maximum 32 C (90 F) and although hot all year round, there is a very pleasant breeze.

There are only two seasons: the hot and rainy season runs from May to November (May-June are the wettest months) and the dry season (winter) runs from December to April. It is the time when Europeans go there in pursuit of the southern sun. Avoid the peak hurricanes season (September-October) and the busy periods (July and August) when the Cubans take their holidays.

Visas Make sure you get the right visa for your visit. As well as tourist visas, there are other visa categories for different types of travellers. If you’re entering Cuba as a tourist, you’ll need to get a tourist card before you travel.

Passport validity: Your passport should be valid for the proposed duration of your stay. No additional period of validity beyond this is required.