1 877 412-8527

Cuba Under Sail

Cuba Cruise

Summary : Immerse yourself in Cuban culture as you visit with friendly locals, savor traditional cuisine, tour the Arte Corte interactive museum, and enjoy musical performances, including a visit to the Buena Vista Social Club. Travel with ease aboard the intimate, 56-guest sailing ship, Le Ponant, the perfect way to see the sights and enjoy the exquisite coastal scenery. Visit the citadel of San Pedro de la Roca in Santiago and stroll through charming, colonial Cienfuegos; both are UNESCO World Heritage Sites. Snorkel or dive over healthy coral reefs to view colorful tropical fish, turtles, sting rays, and other sea creatures. Stroll the atmospheric streets of Havana to discover stunning colonial architecture and sun-splashed plazas, where classic American cars complete the scene of a by-gone era.

This trip will be conducted under a General License – Humanitarian project (section 515.575).

Activities : Birding, Culture, Diving, Snorkeling


Groups of 8 or more people save 10% per person off the cost of the expedition.

Prices from
$999,999,999 to $0

View All Rates

Day 1
Depart Home / Miami

Board your independent flight to Miami. Check in to the Sheraton Miami Airport Hotel for a welcome dinner and briefing.

Day 2
Miami / Havana, Cuba

Board a charter flight to Cuba’s colorful capital. Check in to the five-star Meliá Cohiba, which overlooks the city’s famous three-mile-long Malecón. Enjoy dinner at one of the city’s finest paladars (family-run restaurant).

Day 3

Get acquainted with Old Havana—a UNESCO World Heritage Site—on a walking tour this morning. After lunch make a stop at El Floridita Bar—the birthplace of the daiquiri and one of Hemingway’s favorite watering holes—on the way to visit Arte Corte, a hair salon and museum that preserves the history of hairdressing in Cuba. This evening, climb into one of Havana’s vintage cars for a stylish ride to Rio Mar for dinner, then enjoy a performance at the legendary Buena Vista Social Club.

Day 4
Havana / Embark Le Ponant

Follow the footsteps of Ernest Hemingway at lovely Finca Vigia, where “Papa” lived for two decades. The house is now a museum with more than 20,000 of the author’s personal items. Then visit the fishing village of Cojimar, which inspired his Nobel Prize-winning novel, The Old Man and the Sea. Hemingway loved Cuban cigars and rum, and you will learn about the history and production of both during visits to Conde Villanueva Cigar Lounge and the Havana Club Museum of Rum. Embark Le Ponant this afternoon.

Day 5

Lovely Matanzas is intersected by three rivers, and called the “City of Bridges” for the 17 bridges crossing them. Enjoy a full day tour to La Arboleda, a riverside ranch where you can go on a nature walk, go horseback riding, or take a swim in this peaceful setting. Enjoy a typical Cuban lunch before heading out on a 4x4 Jeep excursion through Rio Canimar Nature Park and take a cruise to admire the flora and fauna along the riverbanks. Continue to Cuevas de Bellamar, a fantastical cave system. Or, choose a half day tour of Matanzas with an afternoon at leisure to explore on your own.

Day 6
Cayo Guillermo

Zodiacs take you ashore at Cayo Guillermo for a day of snorkeling and diving in the crystal-clear waters teeming with colorful reef fish. Or, choose to visit the village of Moron, which offers horse-drawn carriages and small shops to browse.

Day 7
Gibara / Holquín

Visit some of Holquín’s many beautiful parks; the San José Church; Cathedral of San Isidoro, dating from 1790; the galleries inside Centro Provincial de Arte and Bayado (Provincial Center of Arts); and Chorro de Maita Museum, which provides great insight into the Taíno Indians, the native Cubans who were wiped out by Spanish conquistadors. Or, choose to remain in Gibara for an afternoon of snorkeling and diving.

Day 8

After breakfast, take a tour of Baracoa, founded in 1512 by Diego Velazquez, Cuba’s first Spanish governor. Walk along El Yunque trail, passing through lush forest that provides habitat for Cuban trogons, Cuban emeralds, and beautiful butterflies. Continue to Rancho Toa, set along its namesake river, where you can take a refreshing swim and enjoy a typical Baracoan lunch. In the afternoon, head to Finca Duaba for the chance to taste Chorote, a traditional drink made from cocoa.

Day 9 – 10
Santiago de Cuba

Founded in 1514 and designated a UNESCO World Heritage site, Santiago was the starting point for expeditions led by Cortés and de Soto. Arrive midday, then head to San Juan Hill, where the conquest by American troops during the Spanish-American War led to Spain’s surrender in 1898. Visit Moncada Garrison, where a young Fidel Castro led an armed assault on the barracks in 1953—the first salvo in the Cuban Revolution. End your day of touring at Morro Castle, another UNESCO World Heritage Site and the most complete, best-preserved example of Spanish-American military architecture in the Americas. After dinner on board, step out to enjoy some local nightlife with Cuban music at Casa de la Musica.

Admire some of the island’s most amazing architecture and historical sites in Parque Céspedes, the heart and soul of Santiago de Cuba. Visit the Cathedral and the First Governor’s House, which houses the Colonial History Museum. Stroll through the Santa Iphigenia Cemetery, then head to the city outskirts and Cuba’s sacred pilgrimage site, the Basilica of La Virgen del Cobre. Time permitting, visit the Botanical Garden; established in 1860 on a former coffee plantation.

Day 11 – 12
Casilda / Trinidad

After a morning at sea, arrive in Casilda and drive to Trinidad, a picture-perfect Spanish colonial town which seems frozen in time. The rest of the evening is yours to wander the cobbled streets filled with 19th-century mansions, guajiros with their donkeys, and troubadours strumming guitars. Witness the atmosphere come alive, perhaps enjoying a pre-dinner cocktail ashore before dinner back onboard; or stay in Trinidad for dinner on your own.

Today, choose between a morning walking tour around Trinidad; a living-museum of Spanish colonialism, the entire city—even its red-tiled roofs—was declared a UNESCO World Heritage Site. Then return to the ship for lunch and an afternoon at leisure. Or, opt for a full day at Guanayara National Park; hike through the jungle and learn about the various species of indigenous plants, some of which are still used as herbal remedies. Enjoy lunch at Casa La Gallega, a delightful Creole restaurant surrounded by tropical blooms 1,800 feet above sea level.

Day 13

With its French spirit and fabulous setting along Cuba’s most spectacular bay, Cienfuegos earns its moniker, “Pearl of the South,” and its UNESCO status for its outstanding architecture, which you discover on a guided walking tour. After lunch on board, visit one of Cuba’s finest jewels: the Spanish-Moorish Palacio Del Valle, dating from 1917 and displaying masterful mosaics, ironwork, and other ornamentation. Then take a leisurely stroll through the Botanical Gardens, set in an old sugar mill complex.

Day 14
Cienfuegos / Disembark / Playa Larga

After breakfast, disembark Le Ponant and head to the UNESCO-designated Zapata Wetland region. View some of the local wildlife at the Fiesta Campesina zoo-park before touring the Playa Giron (Bay of Pigs) Museum; located at the site of the unsuccessful military invasion by U.S.-backed anti-Castro forces in April 1961. After lunch at a local restaurant, continue to Playa Larga and check in to the Playa Larga Hotel.

Day 15
Playa Larga

One of the Caribbean’s largest and best-preserved wetlands, the Zapata Swamp is a birder’s paradise, and a full-day tour of the La Turba area introduces you to the natural history as you search for endemic species such as the Zapata wren and Zapata sparrow. After lunch, continue to Salinas, an area of mangrove swamps, coastal lagoons, and forest that provide refuge for more than 150 indigenous and migratory birds. Or, choose a day of snorkeling and diving at Caleta Buena where a pristine coral reef hugs the shore. Meet with the Director of the Zapata National Park before dinner at the hotel.

Day 16
Playa Larga / Havana

This morning return to Havana, with a stop at the Korimacao Cultural Project en route. This cultural facility offers residents from surrounding communities the chance to develop and hone their skills in acting, singing, dancing, and music. Enjoy lunch along the way, then check in to Meliá Cohiba. Your farewell dinner tonight is in the Sierra Maestra Restaurant, situated on the 25th floor with jaw-dropping, 360-degree views over Havana.

Day 17
Havana / Miami

After breakfast, transfer to the airport for your return flight to Miami and connect with your homeward flight.


This itinerary is subject to change. ExpeditionTrips.com is not responsible for itinerary changes.

Mandatory Insurance:
The Cuban government requires travel insurance (which covers at least medical expenses) to be compulsory for all travelers to Cuba. Proof of travel insurance will be requested at Havana airport by immigration officials. Travelers failing to produce a valid document will be required to purchase a new policy at the airport, for permission to enter Cuba.

Gratuities; accommodations as per the itinerary; group meals including beer and wine with lunch and dinner; gear certifcate; groups transfers on arrival and departure dates; guided excursions as stated in the itinerary; entrance fees at sites; and medical expense coverage and emergency evacuation insurance. Subject to change without notice.

Not Included:
Airfare; excess baggage charges; airport arrival and departure taxes; transfers for independent arrivals and departures; passport and/or visa fees; travel insurance; items of a personal nature such as laundry, bar charges, alcoholic beverages other than mentioned as included, e-mail/Internet/fax/telephone charges; fuel surcharge may apply.

Would you like to learn more about this trip or request availability?