10 Days/9 Nights


10 Days/9 Nights

Join us in a 10 day/9 night exploration of Cuba’s pristine Northwest coast for a cultural immersion without parallel. With more than 2,000 nm of coastline, 20 marinas and nautical centers, and a vast archipelago made up of more than 4,000 islands and cays. Cuba is an ideal destination for yachters. Although there are few yacht owners in Cuba, the country has a long tradition of yachting. You’ll encounter few private vessels but we’ll introduce you to nautical experts from the Hemingway Yacht Club who will explain, in detail, the state of Cuban yachting initiatives and goals.

Arrive in Havana to a unique city with the spirit of a grand metropolis and the charm of a mid-century seaside resort, a living, vibrant, and unique scenario waiting to be embraced. Follow on Hemingway’s footsteps to understand the deep cultural ties between the US and Cuba, share your experiences with local fishermen, scientists, environmentalists, and educators who are he stewards of Cuba’s marine environment. Hit the dance floor to the sensuous rhythms of the island’s world-renowned music scene, and assist Havana’s foremost chefs for unforgettable culinary experiences. Enjoy private concerts and dance rehearsals and partake in Cuba’s dynamic art scene. Our sojourn will also take us to several UNESCO World Heritage Sites, such as Old Havana and the Viñales Valley, where world’s the best cigars are hand rolled. We’ll end our trip in the legendary resort town of Varadero.

Yachting to Cuba from the US is completely legal for vessels of all sizes and all flags under our OFAC-compliant itineraries. Yachters qualify under 12 categories including, but not limited to, humanitarian, environmental, historical, or cultural people-to-people exchanges. Our programs can be customized to cater to our guests’ whims and wishes.

Guest have the option of sailing with the crew or we can arrange private or commercial flights into Havana.


  • OFAC Compliant Itinerary
  • Navigation plan assistance
  • 24 hour concierge services
  • Liaison with marina personnel and Cuban authorities
  • Cuban cruising permit
  • Pre-tour overview and orientation
  • Meet & greet and private ground transfers in Cuba
  • Marina reservations, dockage, off-shore anchorage, and stocking
  • Daily private cultural encounters
  • All-inclusive resort beach, pool, restaurants and bars at Marina Varadero
  • Day trip to Cayo Blanco (on anchor) and swim with the dolphins
  • Refreshments including fresh juices, snacks and water while touring
  • TOCA Trips exclusive programming and custom designed cultural encounters
  • Expert logistical staff, tour guides, and cultural docents
  • All entrance fees to scheduled activities and events
  • Programmed meals on land
  • Gratuities for restaurant services and programmed activities
  • Navigation permits, insurance, and charts

NOTE: This itinerary can be customized to suit the guests cultural preferences and tastes. Children and crew programs available upon request.


Additional information

Tour typeBoating, Nature

Day 1:Havana

Following your arrival at Marina Hemingway, our staff meets with guests for the first daily briefing. TOCA Staff will also meet with the captain and crew to secure stocking and navigation details. Lunch awaits at Santy Pescador, a catch-of-the-day riverfront restaurant serving the freshest seafood in town. In the early evening, you will be picked up or a twilight tour in Havana’s iconic vintage convertibles that includes Quinta Agenda, Modern Havana, Plaza de la Revolución, and Vedado. We’ll stop at Hotel Nacional for welcome cocktails and refreshments before continuing to dinner at San Cristobal, a classic Cuban paladar, where President Obama and his family had dinner during their historic trip to Cuba.


Day 2: Havana

The rich history and architectural wonders of UNESCO World Heritage Site Old Havana await on Day 2 of your Havana experience. Stroll through the area’s main squares and monuments by the hand of one of the city’s historians, with a stop to visit Ernest Hemingway’s room at the Hotel Ambos Mundos. Lunch awaits at the hip yet sophisticated Paladar Havana 61 followed by a sublime musical encounter with the Coral Carolina vocal ensemble inside a baroque 18th century monastery.

Dinner will be served at Havana’s hottest culinary ticket, La Guarida. La Guarida is the place where Cuban cinema meets haute cuisine. It was the set of the 1993 Oscar-nominated film Fresa y Chocolate. Following dinner, we’ll have an afterglow at the restaurant’s breathtaking rooftop terrace for cordials and cigars before our fleet of vintage cars takes you and your guests, in style, to the world-famous Tropicana nightclub. From your VIP table, you’ll have the best views of the emblematic show featuring the best of Cuban music, dance, and pageantry.


Day 3: Havana

American novelist and Nobel Prize Laureate Ernest Hemingway lived in Cuba for a period of 20 years. There, he wrote some of his most celebrated works, including The Old Man and the Sea, the story of a Cuban fisherman who battles a giant marlin in the Gulf Stream for six days. We start the day with a guided tour of Finca Vigía, Hemingway’s former home, now a museum, where time seems to stand still. An authentic Cuban lunch and cigar pairing awaits us at El Ajiaco in the fishing town of Cojímar, where the American writer kept his beloved yacht, Pilar. After lunch, we return to Havana for an afternoon stroll through the city’s majestic Prado Boulevard and cocktails at the elegant Gran Manzana Hotel’s rooftop bar with unforgettable views of the city’s neoclassical landmarks. Dinner is served at El Cocinero before we end the night at Fábrica de Arte Cubano (FAC), Havana’s hip multidisciplinary space, where we’ll enjoy simultaneous artistic displays, from cinema and theater to performance and the visual arts. Dance the night away to the nightly live music.


Day 4: Viñales Valley

The Cuban countryside is bucolic and enchanting. Guess will be treated to an all-day excursion to the Viñales Valley, a natural park and biosphere reserve declared World Heritage site by UNESCO, where they will bask in the majestic beauty of the pristine landscape of the province Pinar del Rio. A People-to-People educational encounter is scheduled at a working tobacco plantation where you learn the fine art of cigar making, cultivation, and consumption. Lunch awaits at the Finca Agroecólogica el Paraiso, which is a prime example of farm to table sustainable practices that are being encouraged throughout the Island. Back in Havana, we’ll have dinner at the elegant Cafe del Oriente, which was the restaurant chosen by the US State Department for Secretary John Kerry’s official luncheon after the re-opening of the US Embassy in Cuba followed by a stroll through romantic Old Havana at night, when the tour buses have departed and the area turns into an enchanting maze of dimly lit cobble-stoned streets dotted by restaurants, parks, cafes, and rooftop bars.


Day 5:Havana

We begin our fifth day in Havana with a photographic tour off the beaten path. We’ll venture into some of the city’s less visited areas to capture the real essence of the Cuban people. We’ll have lunch at the charming Doña Eutimia, located on Cathedral Square. After lunch, we’ll have free time for shopping and visiting particular points of interest. In the evening, you’ll be picked up for a private concert and dinner at a colonial villa by one of Cuba’s foremost music ensembles. We will provide a list of available performers and music genres for the concert at our pre-tour orientation session.


Day 6:Havana

The local staff prepares all the documentation and payments for departure from Havana. The yacht sails to Varadero where they will be met by the staff. Guests will have access to all the marina amenities plus day passes to the Melia Marina Hotel. Varadero is located in the province of Matanzas, the cradle of Afrocuban tradition and folklore and the main point of entrance for African slaves into Cuba. After arrival, we prepare for a sunset tour of iconic Varadero to visit the main sites, including the Dupont Mansion, where plastic magnate Irénée Dupont built his grand vacation home. After cocktails at Dupont, dinner and music await at the popular Yaco Club.


Day 7:Varadero

After a morning conversation with local fishermen and marine biologists to understand the state of the coastal environments and surrounding coral reefs, we invite you to a day on the hook near one of Varadero’s greatest attractions, Cayo Blanco. The cay is about 10 miles from the marina, and the pristine beaches are an invitation to relax. Enjoy a beachside seafood picnic and have a day to play with your water toys and other marine sports. After lunch, we proceed to the Varadero Dolphinarium for a delightful swim with wild dolphins before returning to the marina. Dinner will be served aboard, and our tour leader will have the nighttime options ready for you to choose how to end the night.


Day 8:Matanzas

We spend a relaxing morning at the beach before heading to the nearby city of Matanzas, a place where literature, music, dance, and folklore coexist and flourish in amazing harmony. We’ll have a light lunch at one of the city’s popular eateries followed by a private musical showcase featuring Afrocuban religious drumming, chanting, and dancing. An unforgettable experience that will leave you breathless, cleansed, and energized.We return to Varadero for dinner at the Marina’s finest restaurant, KCHO, owned by one of Cuba’s most prominent contemporary artists.


Day 9:Varadero

The white sandy beaches along Varadero’s coast are so delightful, they merit a second visit. You’ll be treated to a beachside champagne lunch before a well deserved afternoon at the spa. We say good bye to Cuba with a private musical showcase and dinner in one of Varadero’s finest venues.


Day 10:Varadero - USA

Our team prepares all the departure documentation and payments for a quick departure from Marina Varadero to the USA. You say farewell to this enchanted island bringing back treasured memories, new friends, and a new appetite for life.