Insider’s Cuba

¡Bienvenidos a Cuba! 

We meet at the Jose Marti International Airport where our lead guide will gather the group before a thirty-minute drive into Cuba’s largest city—Havana (spelled Habana in Spanish). As we drive to the city, our local guide will share history and insights about the area.

We’ll head to Old Havana where you’ll stroll along the famous Paseo del Prado, the main boulevard connecting the sea to the heart of Old Havana in Central Park. This tree-lined promenade is filled with historical relevance, as it was designed in the 18th century and was the first paved road in Havana. The buildings and homes seen here are architectural marvels, and the wide boulevard has become an impromptu market with local artists displaying their works. Here we will stop and talk with local vendors and private business owners to learn more about their lives and lend support to the local economy.

After we check in to our casa particular (privately owned bed & breakfast), we’ll gather for a welcome dinner at a paladar (privately owned restaurant). (L, D)

Havana Vieja (Old Havana) 

We begin the day with a visit to the Antonio Núñez Jiménez Foundation, a non-governmental organization (NGO) based in Cuba. Here you’ll have a chance to speak with a representative from this organization regarding their research programs and conservation efforts taking place in Cuba.

Following this hour-long visit, we explore Habana Vieja (Old Havana) and wander the narrow streets, bustling neighborhoods, and local markets where the colonial past is still very much alive. Our exploration includes Old Havana’s four main squares: Plaza de la Catedral, Plaza de San Francisco, Plaza de Armas, and Plaza Vieja. On our tour, we may have the chance to stop by one of the thriving private enterprises in Havana and talk with some of the staff about their struggles and successes with operating a business in Cuba.

We enjoy lunch at a nearby paladar, one of the new waves of privately-owned restaurants in Havana that have drastically changed the dining experience in Cuba. Paladars are becoming known for their excellent service and increasingly upscale take on Cuban home cooking – a real treat! In the afternoon you’ll be able to further explore Old Havana or the Vedado neighborhood on foot, or visit one of the many museums on your own.

We’ll end the day with a sunset dinner in the enchantingly creative home of artist Jose Fuster in Jaimanitas, located on the outskirts of the city. Afterward, you’ll have a chance to check out some live music at one of the many hot spots making up Havana’s unique nightlife. (B, L, D)

Havana and the Viñales Valley

This morning we’ll take a scenic drive two-and-a-half hours westward to reach the Viñales Valley to visit with a local farmer and learn about coffee cultivation. We’ll learn about the process from the plant to the roasted bean and perhaps have a chance to taste his freshly brewed coffee.

We will hike the paths in the valley of Viñales National Park with our local, expert guide. Here we get a chance to see the countryside of Cuba and how traditional ways of farming and living have been maintained throughout the years.

Lunch today will be a farm-to-table meal prepared at an organic farm with fresh local ingredients and beautiful views.

We then return to Havana early evening, in time to enjoy dinner on your own at one of the many paladars in Havana. Your guide will be able to assist you with making a reservation or recommendation. (B, L)

Havana by Bike and Playa Larga

Today, we’ll hop on electric cruiser bikes and embark on a tour of the city, stopping at various must-see spots and some lesser-known hidden gems. Our bike tour will be led by another local guide and will take us to some of the more off-the-beaten-path locations in Havana, including various embassies and former mansions that are homes of ambassadors or ministries. During the tour, we’ll stop at one of Havana’s various community projects, where you’ll have the opportunity to provide a donation if you choose. We end our bike tour with lunch and then leave for our next destination, Playa Larga.

During the 2 ½-hour drive to the south coast, you’ll have the opportunity to talk more in-depth with your guide about issues relating to Cuban society, history, and culture. Or you can simply enjoy the scenery. 

At Playa Larga, we’ll check in to our casa particular before heading out to explore this seaside town on the Bahía de Cochinos (Bay of Pigs). Playa Larga first went down in U.S. history as one of the invasion sites during the Bay of Pigs, but now it has a more pleasant reputation as a diver’s utopia. Coral reefs, flooded caves, and colorful marine life give the bay a peaceful Caribbean ambiance. If time allows, we’ll explore and play in the water before we gather for a delicious dinner featuring more Cuban cuisine. (B, L, D)

Cienfuegos and Trinidad 

After a hearty breakfast and strong Cuban coffee, we head to Cueva de los Peces for snorkeling. You’ll have a chance to swim in the crystal-clear water and see the mushrooming coral reef up close while swimming among tropical fishes. (This activity is subject to weather and sea conditions.) We’ll also have the opportunity to swim in a cenote.

Later, we’ll continue our journey east to the beautiful town of Cienfuegos and enjoy lunch at a paladar overlooking the water. This winsome, seafront city has such an ethereal allure that it’s known as the “Pearl of the South.” After lunch, we set out to explore the town with its charming waterfront and colonnaded streets. We eventually make our way to Teatro Tomás Terry, a 19th-century theater well-known for its grand mosaics and whimsical frescoes. Along the way, we visit various local craftspeople and artisans to talk one-on-one with them and learn more about what they do.

This afternoon we continue on to Trinidad, a charming colonial town just an hour away. We take a walking tour of this intriguing town before checking in to our casa particular for the evening and enjoy dinner at one of the many private restaurants. (B, L, D)

Trinidad and Topes de Collantes National Reserve

Our Cuban adventure continues to Topes de Collantes National Reserve, high in the Escambray Mountains. At over 1,000 feet above sea level, this reserve is a hiker’s paradise offering various trails to explore and gorgeous viewpoints. You may be lucky enough to see endemic birds and animals along the trail, such as the trogon.

We hike with an expert on local flora & fauna and, depending on our choice of trail, may encounter a refreshing waterfall – perfect for a swim. Once we’ve worked up an appetite, we’ll enjoy a traditional lunch of roasted pork, potatoes, beans, and rice in the countryside.

If time allows this afternoon we’ll enjoy a sunset walking tour of Trinidad, a UNESCO World Heritage Site. Tonight you’re free to dine on your own at the paladar of your choice. As night settles in, you can explore the music house which has live music along the steps of the main plaza. (B, L)

Cojimar, Havana and Classic Cars

After breakfast, we say adios to Trinidad and begin our journey back to Havana, about a 4-hour drive. On the way, we’ll stop at Cojimar, a picturesque fishing village that was Hemingway’s inspiration for The Old Man and the Sea. Here we’ll enjoy lunch at a private paladar where their specialty is ajiaco, a rich stew with pork, corn, and other delicious ingredients.

Back in Havana, we’ll visit a classic car repair shop and talk with the repairmen about their processes for fixing old cars and the difficulty of getting parts. Afterward, we can enjoy a ride through the streets of Havana in their restored classic American cars.

This evening we share our favorite stories during a farewell dinner as a group. After dinner, you’ll have the opportunity to visit Havana’s Fabrica de Arte, an old peanut oil factory that has become an art and music collaborative, one of Havana’s most popular spots for Cuban youth and tourists alike. (B, L, D)

Adios Havana!

We awake for our last group breakfast before heading to the airport for departing flights. We offer two scheduled airport transfers, one in the morning and one in the early afternoon, both timed to accommodate various flight times. Exchange any extra currency you have left over before catching your return flight home! (B)