Latin America Vacation
Cuba Unique Holiday | Trinidad to Havana
Have the time of your life in Cuba over the holidays
8 Days / 7 Nights
Activity LevelActivity levels are subjective depending on your general level of fitness and your experience; however, all of our trips are self-paced.
Moderate to Challenging
On this eight day adventure, Cuba will both transport you back in time and help you ring in the new year! Get a taste of true Cuban culture, holiday celebrations, traditions, everyday life, and its history. Cuba, a slow-moving historical time capsule, comes to life through 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, personal encounters with the people and places of Cuba and provide unforgettable memories to last a lifetime. Celebrate the holidays the Cuban way with rum, dancing, cigars, and music performed by talented locals.
- Take in sights of the countryside and small towns, to Cienaga de Zapata National Park which features Cuba’s largest wetlands, one of the country’s most biodiverse regions home to over 200 species of birds
- Kayak at Playa Larga in Salinas de Brito, paddling through mangroves and cays of the Zapata Swamps
- Travel through time on horseback as you explore Cuba’s colonial history in Valle de los Ingenios where the world’s sugar production once originated
- Cruise in a vintage convertible through the fresh seaside air, taking in the cityscapes and people of the city on your ride that ends in Parque Central and the Capitol area
- Connect with impressive musicians and learn to dance with a professional salsa instructor
- Meet humble and talented muralist named Maisel in his home and learn about Cuban life on an authentic level
- Splurge on an optional glitter and glamor show at the Tropicana Cabaret and a bottle of rum at your private table
A few more reasons why you’ve gotta go
The colorful scenes: Art, music, and dance layer the life on the streets and in the restaurants
The traditions: Interact with the locals as they prepare for their huge annual celebration of New Year’s and engage in unforgettable interactions with Cuba’s people-scapes
The history: Since the 1959 Revolution, a fascinating history has unfolded and today, the door has been opened again for Americans to visit and enjoy its creative culture
Jose Marti International Airport HAV
Jose Marti International Airport HAV
Fly into Havana’s Jose Marti International Airport, 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. Check into your accommodations for one night in Havana. Your guide will host you this evening for a welcome dinner at a traditional Cuban paladar. Get an overview of your tour program, led by your guide, and get any questions you might have answered.
Havana / Trinidad / The Bay of Pigs
Begin your journey into Central Cuba and the island’s colonial past while eating breakfast on the go during your transfer to Trinidad. Drive southeast about two hours, taking in sights of the countryside and small towns, to Cienaga de Zapata National Park. This park features Cuba’s largest wetlands and is home to over 200 species of birds and is one of the country’s most biodiverse regions. Kayak at Playa Larga in Salinas de Brito, paddling through mangroves and cays of the Zapata Swamps. Enjoy a picnic lunch. Explore the famed Bay of Pigs where the 1961 failed U.S.-led invasion took place. Walk through a local museum to learn about the infamous event from the Cuban perspective. Arrive in Trinidad tonight and unwind before dinner that will take place at your accommodation or a nearby paladar.
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.
Travel through time on horseback as you explore Cuba’s colonial history in Valle de los Ingenios. Trinidad, a UNESCO World Heritage Site, was once the center of the world’s sugar population, originating from this valley! You also have the option to meet a local potter in his studio and learn to make traditional Tinitario pottery. Lunch will be served at a paladar. Discover the city of Trinidad on a walking tour. Meet a Cuban woman who is a local artist. If time permits, we will visit two interesting museums in the Plaza Mayor, Trinidad’s city center. The night is yours to explore the pastel streets and choose a paladre for dinner or enjoy a meal at a paladar that has reservations available. Be entertained with live salsa dancing and music after dinner at the Casa de la Musica.
Cienfuegos / Havana
After breakfast, stop in Cienfuegos on your way to Havana, Cuba’s capital. Cienfuegos is Cuba’s only city founded by the French. Enjoy a walking tour of the city center and a cocktail at a rooftop bar for a view of the layout of the city. Eat lunch at a seaside paladar in Cienfuegos known for their al carbon (grilled) dishes. Continue driving to Havana, arriving by 5 pm to check in to your accommodation and relax before dinner • Chow down on some Italian food this evening for a change.
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…
Today we ride in style! After breakfast, cruise in a vintage convertible through the fresh seaside air. take in the cityscapes and people of the city on your ride that ends in Parque Central and the Capitol area. Your guide will enlighten you with details of the country’s history, architecture, and romance of La Habana Vieja (Old Havana). Its location, port, and reputation for being a wealthy city have made it a coveted jewel by the British, Spanish, and Americans for centuries. Lunch will be served at a favorite paladre in Old Havana. The afternoon is yours to enjoy at your leisure. Encounter an accomplished guitarist playing authentic music before dinner. Reservations at Tierra inside the famed Fabrica de Arte Cubano are ready for a Latin-inspired dinner. Explore the inner workings of Fabrica de Arte Cubano full of art, music, and dancing.
Following breakfast, bike through the less-visited Centro Habana neighborhood. Stop along your route to learn how the average Cuban lives and works in this often misunderstood country. Watch local prepare for their biggest celebration of the year! Enjoy lunch at Centro Habana paladar that hosted a former US President and many VIPs. Sip on rum, cocktails, mojitos, or daiquiris mixed by a professional barman during a cocktail lesson. Begin to dance like a local after a few drinks with help from a professional salsa instructor! Finally, you’ll get to join in on the New Year’s Eve fun with locals and visitors the authentic Cuban way.
Happy New Year! Celebrate the holiday beginning with a late morning cooking class led by a local chef with lunch included. Connect with a humble and talented muralist, named Maisel, whose larger than life-sized murals of children adorn the city. Meet him in his home and learn about Cuban life on a real level. Visit Jaimanitas, a neighborhood that’s been whimsically transformed into a surreal canvas for famous Cuban artist Jose Fuster. End your holiday at the iconic Hotel Nacional with a tour through the Hall of History. Here, photos and memorabilia from all distinguished hotel visitors dating back to 1930 are featured. Cheers to the week with a cocktail in the gardens overlooking Malecon (seaside avenue). Eat as a group at a paladar considered one of Cuba’s best, La Guardia. This location was the backdrop for the film Fresa y Chocolate. An optional glitter and glamor show at the Tropicana Cabaret is scheduled to run for $139 USD per person including transportation and a bottle of rum at your table.
Spend your morning the way you’d like. You will be transferred to the airport by your team.
* This trip is operated in partnership with TerraVersed.
**Trip itineraries are subject to change without notice due to road, weather and other factors outside
of our control, for the safety and enjoyment of our guests, as deemed necessary and appropriate by
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
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 National Park on Day 3. No experience necessary. Equipment and instruction will be provided.
Bicycling: Easygoing bicycle tour through Centro Habana on Day 6 (3 hours plus 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: The sights, sounds, tastes, and smells of this country are mesmerizing. 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 and enjoy its creative culture. This open door leads to incredible opportunities for learning and immersion into a complex culture and world full of art, music, dancing, food, and drink. You’ll have the opportunity to interact with the locals as they prepare for their huge annual celebration of New Year’s. 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 crenellated 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.
Austin Adventures guides are experienced facilitators and regional experts. They will take the time to explain the details of each activity, answer any questions and demonstrate the use of all equipment. Each activity has been carefully planned to include options for all levels. Most importantly, Austin Adventures guides will help you select the distance that’s right for you.
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.
Included in the Trip Price
• In country Cuba Concierge, available 24/7
• Private services of guide, driver & air-conditioned vehicle
• Private arrival & departure transfer
• Activities, entrance fees, and touring as detailed
• Meals as per noted in the itinerary
• 2 domestic drinks (sparkling or still water/sodas/domestic beer/local
• cocktails per person with included meals at paladares
• Bottled water stocked in the vehicle while with driver and guide
• Tips for specialty guides during included activities
• Tips for waiters during included paladar meals
Not Included in the Trip Price
• Gratuities for national guide and driver. Recommended: Guide
• $10 USD per person, per day/ Driver $7 USD per person, per day.
• Meals not mentioned in the program as included
• Air to Cuba and related taxes
• Enrollment in the Cuba medical emergency insurance (mandatory
• by the Cuban government for all travelers to the island). U.S.
• airlines provide in ticket cost.
• MANDATORY Cuban Tourist Card (arranged through the airline)
• Optional activities
• Other expenses of a personal nature such as luggage charges,
• and shopping
- 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.