North America Vacations
Cuba | Havana’s 500th Anniversary | Adult Only
Immerse yourself in vibrant culture and stunning landscapes in a land that was once forbidden
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.
This November, Havana is reaching its half-millennium milestone birthday and we want to celebrate in style! On this eight-day adventure, we’ll journey from Trinidad to Havana, transporting ourselves back in time.
Cuba 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 will end in Havana during the 500th birthday of Cuba’s most famous city, and we’ll be joining the locals for the festivities, celebrations, and special activities that are being planned for this once-in-a-lifetime opportunity. Celebrating Havana’s birthday in addition to experiencing curated, one-to-one encounters with the people and places of Cuba is sure to provide an unforgettable adventure during a special time in Cuba’s history!
Snorkel or kayak along Playa Giron’s shoreline before visiting the nearby Bay of Pigs Museum for a day spent immersed in fascinating history
Horseback ride through Valle de los Ingenios near Trinidad to learn about the history of sugar production through the eyes of a local
Pedal around an off-the-grid Centro Habana neighborhood on a bicycle tour alongside a knowledgeable guide
Learn the ancient art of turning tobacco leaves into a perfect hand-made cigar on an expert-led tour in one of Havana’s largest cigar factories
Listen to an award-winning Cuban guitarist during a private concert for our ears only
Learn the secrets to making the island’s most famous blends from a professional barman during a pre-dinner cocktail class
Ring in the 500th anniversary of Havana in true Austin Adventures style by dancing, listening to music, drinking rum, and celebrating alongside locals and tourists alike!
A few more reasons why you've gotta go:
Havana's 500th Birthday: We've said it once and we'll say it again; you do NOT want to miss out on this once in a lifetime event in Cuba's most exciting city!
Classic Cuba Experiences: Along with celebrating Havana's anniversary we'll be riding in vintage 1950's automobiles, learning about Cuban cigars, and perfecting the art of creating the perfect mojito.
The host: If Austin Adventures own VP of Operations, Kasey Austin, is selectively choosing to host this trip, you know it's going to be one for the books!
Santa Clara, Cuba SNU
Havana, Cuba HAV
Santa Clara / Trinidad
Fly into Santa Clara’s Abel Santamaria International Airport where your guide and driver will be awaiting your arrival. 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 two 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. After lunch, there’s time to visit an unexpected museum that is full of paintings that were seized during that nationalization of Cuba following the 1959 revolution. 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 / Playa Giron / Palpite / Havana
Enjoy breakfast and check out of your rooms by 8:00 AM. Today we transition to Havana, but have some wonderful activities to experience along the way. Our first stop this morning is the seaside town of Playa Giron where we’ll have an opportunity to spend time with local naturalist guides on one of two experiences. For those seeking to get into the water, one local guide will host you on a snorkeling trip. If you prefer to stay above the water, you can join a kayak trip along Playa Giron’s shoreline. Please, note which activity you choose (snorkeling or kayaking) must be chosen 30 days in advance. Day rooms have been reserved to give you time to refresh following your marine experiences. Playa Giron is the home of the Bay of Pigs Museum where you have a chance to learn more about the failed US-led invasion from the Cuban point of view. This infamous event is often thought to be the galvanizing force behind Fidel Castro’s longevity as Cuba’s leader. Lunch is included at a local paladar known for traditional seafood dishes. On our way out of Zapata, near Playa Larga, we will stop at Palpite to see the world’s smallest bird up close: El Zunzuncito (the bee hummingbird). 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…
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 at a paladar that many would consider the best in all of Cuba. Your exploration continues in style, on board vintage 1950s automobiles that will take you on a panoramic tour of the city along the Malecon and across diverse neighborhoods. Afterwards, we’ll learn the secrets of making a few of Cuba’s most famous mojitos and daiquiris under the guidance of a professional barman. This afternoon, we have a special experience enjoying the authentic music of an accomplished guitarist and will 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 day. Dinner tonight is reserved at Tierra, inside Fabrica de Arte, payable directly. After dinner, you’ll have time to explore Fabrica de Arte Cubano (FAC), an amalgamation of art expo, nightclub, local meeting place and trendy shopping venue, and your driver & guide will be available until 12:00 AM this evening for your convenience.
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. Next on our agenda is a visit to a private workshop that produces hand-carved, extremely detailed humidors that have fetched upwards of $100,000 at auction. The meticulous artistry of Humidores Havana is simply unparalleled. Lunch today is reserved, payable directly, at an artful paladar located inside a transformed colonial-era mansion in the Miramar district. After lunch, you may choose to add an optional maridaje, or rum and cigar pairing at an extra cost. Take some time to refresh following your discovery of cigars today. This evening will be full of great food and celebrations on the eve of Havana’s 500th anniversary. This afternoon, we head out on a walking tour of Old Havana. Your guide is an expert on the history, architecture, and romance of the old city. Its location, port, and reputation for being a wealthy city have made it a coveted jewel by the British, Spanish, and Americans for centuries. You are set to visit all four of the key plazas of La Habana Vieja during your walking tour, for a glimpse of its rich heritage. Dinner this evening is included in an Old Havana paladar, known for its exceptional cuisine. Cubans have an interesting way of celebrating birthdays. Getting together with friends and family the night before one’s birthday is a tradition where everyone dances, listens to music, enjoys rum, and celebrates until 12:00 AM. Tonight, you will celebrate Havana’s birthday, like a local!
Following a busy night, you are scheduled to start your day a bit later. Events for Havana’s 500th Anniversary celebration are being finalized and will include multiple venues across the city. Our team has arranged a few special experiences to commemorate this once-in-a-lifetime event. Lunch is sure to be a treat in Old Havana when a special guest will join us to share more about the extensive history of Cuba’s capital city. After lunch, there will be time to explore on your own. A member of our team will be standing by to arrange transportation back to your accommodations when you’re ready. This evening is going to be a huge celebration so make sure to rest up. Dinner is included this evening in a paladar located in the heart of the anniversary celebration. After dinner, our group is scheduled to experience a special event kicking off Havana’s next 500 years in Cuba style, with music, dancing and fun!
Arrival & Departure
Arrival: On Day 1 of the trip, guests should arrive into Santa Clara’s Abel Santamaria International Airport on JetBlue flight number 387, departing from Fort Lauderdale. 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).
Snorkeling or Kayaking: In the seaside town of Playa Giron, you have the option to choose between a snorkeling or kayaking excursion with a local guide (this activity must be chosen 30 days in advance). No experience necessary for either snorkeling or kayaking. 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 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.
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 itinerary (B = Breakfast, L = Lunch, D = Dinner).
- 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 Vice President of Operations at 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.