Insider’s Cuba

Location International Adventure Level Easier to Moderate Minimum age 12 From $4355
Book Now Call toll-free 1 (800) 346-6277

Explore Havana’s Old City and Cuba’s charming south coast on a guided tour of the heart of Cuba’s vibrant culture and countryside.

Take a deep dive into the cultural heart of Havana, where you’ll visit galleries and markets with expert guides. Enjoy interactions with welcoming Cuban families, farmers, and business owners. Snorkel in the warm waters off Playa Larga then tour Cienfuegos before continuing down the coast to the picturesque town of Trinidad.

Stretch your legs on a day hike in Topes de Collantes National Park, enjoy a traditional lunch in the countryside, visit local artists, and explore the coast. Return to Havana and then see Cojimar, the quaint fishing village that was the inspiration for Hemingway’s The Old Man and the Sea. Visit a classic car repair shop in Havana and go for a sightseeing cruise around the city.

Trip Highlights
  • Tour Old Havana on foot and by electric bike
  • Visit Viñales Valley and learn about tobacco cultivation
  • Explore Playa Larga & snorkel at Punta Perdiz
  • Walking tour of Cienfuegos and visit local artisans
  • Hike to a waterfall in Topes de Collantes National Park

What to Expect

Itinerary & Map

Itinerary at a Glance

We pride ourselves in running a relaxed and flexible schedule. Every Cuba adventure is different depending upon the group, other trips in the area, and sometimes the weather. The following is a sample of what your trip might be like:

Day 1

¡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)

Day 2

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)

Day 3

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)

Day 4

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)

Day 5

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)

Day 6

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)

Day 7

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)

Day 8

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)

Meeting Time & Place


Jose Marti International Airport, Havana, Cuba

Meeting time

By 3:30 PM on Day 1 (flight should arrive by 2 PM)


Any time on itinerary Day 8

Trip Map

A Cuban man stands playing a guitar while an older Cuban man in a wheelchair plays maracas and they sing.

Dates & Prices

2024 DeparturesPrice
November 3, 24$3,770 – $4,355
2025 DeparturesPrice
February 9$3,770 – $4,355
March 2, 16, 23$3,770 – $4,355

All prices per person based on double occupancy.

Book Now



Additional Costs

• Tourist visa
• Mandatory emergency medical & evacuation coverage

Single Supplement


Ways to Save

To book with one of our special offers, call 1-800-346-6277 or contact us today.

The Need-to-Know Info

Trip Details

Included in Your Trip Cost

  • Skilled, professional local guide service provided by our affiliate operator
  • 7 nights lodging in privately-owned casas particulares
  • Meals as indicated in the itinerary (B – breakfast, L – lunch, D – dinner)
  • Airport meet & greet and transfer on day 1; group airport transfer on day 8
  • Sightseeing and activities as noted in the itinerary
  • Ground transportation with certified, professional drivers

Not Included in Your Trip Cost

  • Airfare to and from Havana, Cuba
  • Travel Visa/Tourist Card (required by Cuba)
  • Pre- and/or post-trip accommodation and meals (while U.S. regulations are constantly changing and at times difficult to interpret, it may be illegal to travel in Cuba before and/or after your official guided tour)
  • Airport transfers at alternative times from the group transfer
  • Single supplement
  • Excess baggage charges
  • Airport departure taxes (normally included in your airline ticket, approximately US$25)
  • Insurance of any kind, including a travel protection plan or mandatory emergency medical & evacuation coverage, is required by both OARS and Cuba. Cuba coverage is often included in your airline ticket.
  • Gratuities

Travel in Cuba is relatively new for U.S. citizens and unlike that in most other countries. This is an exciting time to travel as legislation changes along with local amenities. Our Support for the Cuban People itinerary is fully legal for U.S. travelers. You will have a lead guide who is Cuban and a U.S. guide who will be with our group while in Havana. We have selected an ambitious itinerary to see many of Cuba’s natural places and also interact with Cubans on a daily basis to learn about their lives and many of their entrepreneurial activities.

With the demand currently being put on the tourism infrastructure, we may have the need to make minor modifications to the itinerary on occasion. Travel to Cuba can have unexpected changes, but we try to remain as close as possible to the original itinerary. Guests should be open-minded, as services we have come to expect as standard may be lacking or non-existent. In exchange, we’ll experience a place unlike any other—Cuba’s diversity, energy, innovation, warmth, music, culture, and art will envelop us.

Our accommodations throughout Cuba will be in casas particulares. A casa particular is a privately owned bed & breakfast run by a Cuban family. Guests will have separate rooms with private bathrooms (single or double occupancy). In some instances, the group may be split between separate casas, in which case they will be a safe walk of only one to two blocks apart. These accommodations are often better maintained than the government-owned hotels. While the outside of some buildings in Cuba may appear outdated or worn, the facilities inside will be clean and comfortable. All accommodations are air-conditioned and provide a safe for securing valuables.


Cuban cuisine is the result of a mixture of Spanish, Taino, African, and Caribbean influences. The national dish is ajiaco, a stew of assorted root vegetables cooked with pork, poultry, or beef. Other typical dishes include lechón asado (roast pork), fried green plantains (tachinos, chatinos, or tostones), congrí (rice with red or black beans), ropa vieja (shredded beef simmered in a sauce of tomatoes and bell peppers) and roast chicken. Fish and shrimp are also often available. Many meals are served family-style and, due to limited resources, may lack the spices and flavored sauces travelers expect in other international destinations.

We need to know as soon as possible about any dietary restrictions we must consider in planning your trip. If you have food allergies or necessary restrictions, we will do our best to accommodate your needs.

Our trips take place during North American winter and spring, avoiding the uncomfortable heat and humidity of summer. During these months there are influences of cold air masses coming from the north, but they are typically of short duration. In winter, the average daily temperature is around 70°F but may drop to the low 60’s°F during colder days. Annual rainfall averages about 52 inches; more than 60% of that rain falls during the wet season, which extends from May to October. That said, you’ll want to be prepared for rain anytime during your visit.

The north coast, home to Havana, tends to be a little cooler, while the southern coast is warmer. With little precipitation and many hours of sunshine, Cuba is a pleasant country to visit.

Average Air & Water Temperatures

Havana °FSea Temp °F

Before booking your trip with OARS, there are a few important considerations we’d like you to know about.

  • Purchase Travel Protection: In order to take part in this trip, each participant must have a minimum of Emergency Medical Evacuation coverage in place for the dates of the trip. Learn more about the plan we recommend.

  • Essential Travel Documents: A passport and Travel Visa/Tourist Card are required for travel to Cuba.
  • Physical Requirements: Your outdoor adventure will be an active participatory trip. Please inform us of any physical limitations you may have as soon as possible. If you exceed 260 pounds, please give us a call. Make sure you are exercising frequently in the months leading up to your trip and can meet our Essential Eligibility Criteria.
  • Trip Forms: Each participant will need to complete the required trip forms within two weeks of making a booking. If you are reserving within 90 days of departure, your forms must be completed immediately to ensure we can properly plan for your trip.

Reservations and Deposits

An $800/person deposit is required at the time of reservation. Deposits may be made by check, money order, or Visa/Mastercard (American Express and Discover incur a 3% processing fee). Prices are in US Dollars, and all payments must be made in US Dollars. Payment of the deposit establishes your acceptance of our complete Terms and Conditions. Individual departures and trip capacity are strictly limited by the managing agency.

Canceling your trip after your deposit is processed will incur cancellation fees because OARS has absorbed costs on your behalf and will turn others away who would like to book the spaces we’re holding for you. Final payment is due 90 days before departure. Accounts on which final payment has not been received 80 days before the departure date will be canceled without exception.

Cancellations and Refunds

Your deposit is fully refundable, less a 3% processing fee, for 7 days after you book when you submit a deposit 7 days or more before the final payment due date.
If you must cancel your reservation after the rescission period described above, your cancellation fee will be determined according to the schedule below. We regret we cannot make exceptions to the cancellation policy for any reason, including foul weather, poor air quality, wildfire activity, acts of terrorism, civil unrest, or personal emergencies. There is no refund for arriving late or leaving a trip early. For these reasons, we strongly urge you to consider purchasing a travel protection plan.

Date of CancellationCancellation Fee
90 or more days before your trip$250/person
89 to 60 days before your trip$500/person
59 to 30 days before your trip75% of the trip price/person
29 days or less before your trip100% of the trip price/person

Requests to transfer a date will be treated as a cancellation, per the terms above.

Canceled Trips

OARS International and the outfitter Custom Latin Travel reserve the right to cancel any trip due to insufficient registration or other factors that make the trip impractical to operate. Do not make nonrefundable travel arrangements unless you have spoken to your Adventure Consultant regarding the status of your trip.

If a trip must be canceled or postponed due to force majeure (factors outside the control of OARS), OARS will provide full credit for payments made toward future travel, or a refund less a 5% service fee plus any nonrefundable payments made on your behalf to 3rd-party suppliers. OARS will make good faith efforts to recover deposits made on your behalf to 3rd-party suppliers, however, we can’t guarantee recovery of any or all of the advance payments made. OARS is not responsible for expenses incurred by participants in preparation for a canceled trip.

Our Insider’s Cuba adventure is run by an affiliate company and arranged through O.A.R.S. International, Inc.

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