Latin America Vacations
Cuba | Trinidad & Havana | Adult Only
Immerse yourself in vibrant culture and stunning landscapes in a land that was once forbidden
8 days / 7 nights
Activity Level Activity levels are subjective depending on your general level of fitness and your experience; however, all of our trips are self-paced.
Trip Start (arrival)
Trip End (return)
Next available departure
Download PDF Itinerary
On this eight-day adventure, Cuba will transport you back in time.
This island has developed more slowly than the rest of the world. It is visible in the number of 1950s era automobiles still on the road, the colonial façades that dominate the architecture, and most beautifully, in the communal spirit of the Cuba people. This incredible journey from Trinidad to Havana will provide curated, one-to-one encounters with the people and places of Cuba that will provide unforgettable memories to last a lifetime.
- Immerse yourself in the rich culture of Cuba through live music, tasty cuisine, dance, art, and cocktails
- Kayak through tunnels of mangroves in Zapata Swamps National Park on the lookout for flamingos, iguanas, and jutias
- Explore the pastel-lined cobblestone streets of Trinidad, a UNESCO World Heritage Site, alongside an expert guide
- Taste a traditionally brewed sample of delicious coffee from Topes de Collantes in the Escambray Mountains
- Take a cigar factory tour, learn the secrets of creating the perfect mojito, and cruise along the Malecon in a 1950s automobile while discovering Havana
- Dance a salsa or rumba to live music at Casa de la Musica, one of Havana’s famed open-air venues
A few more reasons why you've gotta go:
One reason to travel to Cuba: you can! For more than 50 years, travel between the US and Cuba was strictly regulated and off-limits to most Americans.
The music: almost everywhere you go, any time of day, there is music. Cuban music has an energetic mix of soulful Spanish melodies and lyrical traditions, and dynamic African percussion and beats. And with music comes dancing!
The great weather: Cuba enjoys a warm, subtropical climate, making for a great adventure destination at almost any time of year.
Havana, Cuba HAV
Havana, Cuba HAV
Havana / Trinidad
Fly into Havana’s Jose Marti International Airport, arriving before 1:00 PM EST, where your guide and driver will meet you. Upon collecting luggage and gathering our small group together, you’ll be whisked off to a nearby paladar (privately-owned restaurant) for a light lunch and to get acquainted before transferring four hours to Trinidad. Upon arrival, check into your accommodations and spend ample time unwinding, relaxing, and refreshing before dinner. Dinner tonight is at our B&B where the food quality is outstanding. The intimate environment of La Casona will allow everyone to get to know one another, review the itinerary ahead with your guide, and to ask any burning questions you may have about Cuba
About La Casona B&B
La Casona offers 8 rooms with private bathrooms. This Bed and Breakfast is a Horse Ranch, perfect for those who love nature and animals. La Casona is a hidden gem that offers a unique experience, not found anywhere else in Cuba.
Valle de los Ingenios / Trinidad
Trinidad was once the center of the world’s sugar production. Much of that sugar came from Valle de los Ingenios. We being the journey into Cuba’s colonial past with a horseback ride into the valley with a local expert guide. For those not interested in horseback riding, you can instead meet a local potter in his studio for a hands on experience making your own traditional Trinitario pottery. Lunch today will be at a paladar offering both continental and local cuisine. After lunch, it’s time to explore Trinidad, a UNESCO World Heritage Site with pastel-lined cobblestone streets, historic buildings, fascinating museums, and an artistic side that surprises. During a walking tour of the city, you uncover the rich history of the region and learn more about pre and post-revolutionary Cuba. This afternoon, we meet with a local Cuban artist in their studio to learn what life is like for artists in modern day Cuba. Then, we’ll visit several of the numerous museums surrounding Plaza Mayor, Trinidad’s city center. The remainder of the afternoon and evening are free to explore Trinidad on your own. Tonight, dinner will be on your own. Many of the highest rated paladars book well in advance, so we have taken the liberty of securing reservations at a paladar in Plaza Mayor at 8:00 PM. Of course, you are welcome to dine anywhere of your choosing and enjoy Trinidad however you please tonight.
Topes de Collantes / Trinidad
This morning, we travel into the national park of Topes de Collantes located in the Escambray Mountains. Coffee from Topes is only known by a few, but fetches more than $25 per pound internationally. A local coffee grower hosts you to learn about his life in Cuba and includes a traditionally brewed sample of his delicious coffee. Topes is known for its numerous bird species, scenic hikes, and waterfalls that canvas the national park. Depending on your comfort level, your guide will arrange a morning hike through the tropical forest to one of the region’s waterfalls. Bring along a swimsuit if you’d like to take a dip in the pool below the falls. Lunch today will be in a rustic paladar located in the national park, serving traditional Cuba food. Return to Trinidad late afternoon where you have time to relax and refresh in your accommodations. Enjoy a cocktail at La Casona as the sun sets to reflect on the day and look forward to the evening ahead. Dinner this evening is included at a paladar featuring traditional Cuban cuisine. The location is perfect for those who wish to join your guide after dinner for live music and dancing at Casa de la Musica, Trinidad’s open-air entertainment venue. For the art lover, we also recommend visiting the thought-provoking El Gato Negro gallery, open until 9:00 PM. This gallery showcases the best of local artists, both established and emerging.
Trinidad / Zapata Swamps National Park / Havana
Enjoy breakfast and check out of your rooms by 6:00 AM. Our team will coordinate breakfast to-go, but there will be coffee available before departure. Today we transition to Havana, but have some wonderful activities to experience along the way. Southwest of Trinidad is the Zapata Peninsula, home to one of Cuba’s most prolific National Parks and home also to the Bay of Pigs, scenario of the 1961 failed U.S.-led invasion. This infamous event is often thought to be the galvanizing force behind Fidel Castro’s longevity as Cuba’s leader. Your guide will brief you on the events along the way. Our first stop is at Salinas de Brito, in Playa Larga, for a kayaking experience. Join a national park expert paddling through mangroves and cays of the Zapata Swamps in search for iguanas, endemic jutias, crocodiles, and aquatic birds in their natural habitat. Make sure to bring binoculars! A picnic lunch will be served during your excursion. Day rooms have been reserved to give you time to refresh following your marine experiences. On to Havana! You are scheduled to arrive into the timeless Cuban capital in the late afternoon. We have arranged for immediate check-in at your accommodation where there will be time to relax following a busy transfer day. Dinner tonight will be a nearby restaurant serving Italian food for a change of pace.
About La Reserva B&B
La Reserva is a freshly renovated Colonial Mansion with a mixture of vintage, colonial, and mid-century designs. The in-house art gallery contains works by contemporary Cuban artists. A stay here feels like being at your best friend’s home, if your best friend had an impeccable sense of style…
This morning begins with an expert-led tour of one of Havana’s largest cigar factories where you will learn the ancient art to turn five different aged tobacco leaves into one perfect, handmade cigar. The process has been perfected over the centuries but hasn’t changed much. Afterward, we’ll walk the streets of La Habana Vieja (Old Havana) with a guide as they come to life. Explore the four main plazas and learn about the history, culture, architecture, and romance that has endeared the old town to so many cultures over the centuries. Lunch is reserved at a paladar in Old Havana and payable directly. The remainder of the afternoon is yours to explore Old Havana. Your guide will make suggestions based on your interests and arrange a central meeting point and time for transfers back to your accommodation.
Later this afternoon, visit Havana’s Morro Castle and capture photos of the city from across the bay. Your exploration of the city continues in style, onboard vintage 1950s automobiles that will take you on a panoramic tour of the city along the Malecon (Havana’s seaside avenue) and across diverse neighborhoods. Rum and cocktails are an intrinsic part of Cuba’s heritage. A professional barman will share the secret to making the island’s most famous blends during a pre-dinner cocktail class. Dinner is included at an artful paladar located inside of a transformed colonial-era mansion in the Miramar district.
After dinner, you may opt for an optional maridaje, or rum and cigar pairing for an additional fee. Your guide will recommend nightclubs and music venues for anyone who wishes to go out and explore on their own this evening.
Today we start off with a bicycle adventure through the less visited Centro Habana neighborhood. Our team of local experts has arranged several stops along the route to learn how the average Cuban lives and works in this often misunderstood country. Lunch is included today in a Centro Habana paladar that hosted a former US President and many VIPs.
This afternoon, we have a special experience enjoying the authentic music of an accomplished guitarist. We’ll have the chance to learn about the life of an award-winning Cuban musician in a very personal way. There’s time to refresh at your accommodations after a very busy morning.
Dinner this evening is on your own. Our recommendation is to try Tierra inside Fabrica de Arte Cubano (opens seasonally) or Casa Miglis with its live music and European cuisine. Please, let us know ahead of time if there is a paladar you want to try and our team will ensure you have a reservation.
Meander through a local market and see what ingredients are available to Havana residents today. This is an also opportunity to see Cuba’s two currencies at play and understand their significance and use. Enjoy a cooking class led by a local chef, with lunch included. This is your last afternoon to simply enjoy Havana. It’s a great time to walk the Malecon, explore more of Old Havana, or simply shop for art, souvenirs, cigars, and rum before you depart tomorrow.
Dinner this evening is reserved at a paladar most would consider Cuba’s best. Dinner is reserved for 7:00 PM to ensure there’s ample time to make it to your show. Tickets and preferred seating are included tonight to the famous Tropicana Cabaret.
Enjoy your last night in Havana!
Arrival & Departure
Arrival: On Day 1 of the trip, guests should arrive into Havana’s Jose Marti International Airport before 1:00 PM EST. Your guide and driver will be waiting with Austin Adventures signs just outside of the arrivals terminal. Once everyone’s luggage is loaded, our small group will head to a nearby paladar for a light lunch.
Departure: On Day 8 of the trip, guests may book flights out of Havana’s José Martí International Airport at any time during the day. Your departure transfer will be scheduled approximately 2.5 hours prior to your flight’s departure time.
Hiking: There is one day of hiking in Topes de Collantes on Day 3 of this itinerary. Hikes will be chosen based on the desires of the group as there are several hikes in the area to choose from lasting between 1.5 to 3 hours and ranging in difficulty from easy to moderate to difficult.
Walking: Much of this tour involves exploration by walking. Whether we’re exploring Havana’s seaside Malecon or Trinidad’s cobblestoned streets, you should be at a reasonable fitness level for this itinerary in which you can walk at least several hours at one period of time.
Horseback Riding: Easy walking pace, no experience necessary (optional visit with a local potter can be arranged if you’re not interested in horseback riding).
Kayaking: 3-hour guided paddling tour through the mangroves and cays of Zapata Swamps National Park. No experience necessary. Equipment and instruction will be provided.
Bicycling: Easygoing bicycle tour through Centro Habana on Day 5 (3 hours + stops). This bike excursion is all about getting out and exploring with a different mode of transportation other than with our own two feet. You should be familiar with how to ride a bike to feel comfortable on this experience, but tour will be completed at an easy pace that most guests should have no trouble with.
Discovery: Cuba was a popular destination for Americans until the 1959 Revolution changed it all. Since then a fascinating history has unfolded and today, the door has been opened again for Americans to visit. This open door leads to incredible opportunities for learning and immersion into a complex culture replete with rich and meaningful interactions with the people of Cuba. Engage in unforgettable interactions with Cuba’s people-scapes and staggering natural beauty. The incredible natural beauty of Cuba extends beyond its beaches, and its sweeping swamplands and crenelated mountains are known for their rare wildlife as well as their insurrectionist folklore. Stroll city streets where opulent mansions peer out between suburban city planning. Explore the countryside where dilapidated plantations look out on still-thriving tobacco farms. Cuba is an arresting country of contradictory curiosities. Come experience all of Cuba’s nuances, vibrant culture, and stunning natural beauty.
Evenings in Cuba
Each night while you are in Cuba there is live music happening somewhere, especially in Havana. From salsa to rumba to reggaeton, you can find incredible entertainment throughout this country. Your guide and our in-country concierge will be happy to assist finding options that suit your tastes. Your driver and guide are available until 9:00 PM each night unless otherwise noted in your itinerary. Special evenings during the tour will include the driver and guide until 12:00 AM and the itinerary will be noted accordingly. On these nights, your driver and guide will have to excuse themselves by 12:00 AM to ensure they are properly rested to provide top-quality service and keep you safe during your entire program.
Breakfast if offered at your accommodations and typically is akin to continental breakfast with toast, fruit, juice, and coffee. Each accommodation differs and may offer additional items. Lunches and dinners included are a la carte in Havana and include two drinks per person (soda, bottle water, coffee, tea, beer, or other domestic drinks). There are instances where restaurants may offer pre-fixed menus, especially outside Havana. If you have special dietary requirements, please let us know prior to travel. Meals are included as indicated in the itinerary. (B = Breakfast, L = Lunch, D = Dinner).
Support for the Cuban People Tour Programs
In accordance with the NSPM, OFAC is requiring that each traveler under this travel category engage in a full-time schedule of activities that result in meaningful interaction with individuals in Cuba. Such activities must also enhance contact with the Cuban people, support civil society in Cuba, or promote the Cuban people’s independence from Cuba authorities. Renting a room in a private Cuban residence (casa particular), eating at privately owned Cuban restaurants (paladaeres), and shopping at privately owned stores run by self-employed Cubans (cuentapropistas) are examples of authorized activities; however, in order to meet the requirement of a full-time schedule, a traveler must engage in additional authorized Support for the Cuban People activities.
Activity levels are subjective depending on your general level of fitness and your experience; however, all of our trips are self-paced.1 Easy (1)
Activity levels are subjective depending on your general level of fitness and your experience; however, all of our trips are self-paced.2 Moderately Easy (2)
As President of Austin Adventures, Kasey Austin can tell you the logistical ins and outs of every single trip. More than that, though, Kasey has lived and breathed most of the company’s featured destinations and will eagerly share her contagious passion for the transformational power of active travel. Kasey grew up in the adventure travel business; she knows the positive, lifelong impact of family travel, a quality that earned her the distinction of being named top family travel guide by Outside Magazine in 2014.