Unique Cultural Tours
Unique Cultural Tours
Experience the fine arts of Cuba!
Enjoy lively jazz tunes amongst the laid-back Caribbean culture of this island that is not to be missed! Our ten-day tour gets you VIP access to the best of the Havana Jazz Festival, and our Cuban guide will take you out of the big city to experience the best of Cuban UNESCO World Heritage sites, waterfalls, ocean views, birdwatching, Cuban food, architecture, and Cuban friends who await you on this phenomenal tour!
Note: a detailed schedule of performances is generally released one week prior to the festival.
Cost: $4,195 (market value $6,995). A $500 deposit is due upon registration to reserve your spot.
Don’t delay…Early Bird savings have been extended to Aug. 31, 2025!
Bilingual Cuban Guide
Travel licenses, mandatory Cuban health insurance and visas
9 nights in Casas Particulares, Cuban Bed & Breakfasts. We have discovered the most comfortable lodging in Cuba is in these Casas, versus hotels which are government-owned and lacking in many amenities.
16 meals, almost always at paladares. The paladares of Cuba are unique in that they are privately-owned restaurants where the staff takes great pride in their delicious meals and hospitality.
VIP tickets to the Havana Jazz Festival! This tour includes your admission to the shows.
Private, air-conditioned ground transportation for the whole tour with our own driver.
Purified water included and always available (bring your favorite water bottle for refills).
All group activities mentioned on this itinerary.
Please note: We have an amazing team in Cuba; therefore Jenny & Steve do not attend every tour
Airfare to/from the US (estimate $500)
Trip Insurance
7 meals
Alcohol
Tips
The purpose of this itinerary is to give you an idea of the types of activities you will engage in during the tour, however, it may change based on factors such as availability, weather, and to take advantage of spontaneous activities and events on your trip.
Flights - Arrive in Havana on the first day of the tour and depart Havana on the last day, due to visa constraints. If you are anxious about missing flights, we recommend you fly into Miami the night before. There are many flights between Miami and Havana.
Activity Level - Walking up to three miles a day, often on dirt paths, cobblestones, or other uneven terrain.
Lodging - Comfortable, air-conditioned bed and breakfasts at each destination.
Social Responsibility & Eco-Friendly Practices - Our tours are deeply rooted in these values. We partner with local entrepreneurs for lodging and dining, and we actively limit plastic waste wherever possible.
No vaccines are required for travel to Cuba.
A map of where you’ll go on this tour
'55 Chevy Bel Air driving tour of Havana
Fusterlandia and artists
Hotel Nacional
Sightseeing in Colonial Havana of the 1500s
Hemingway’s home in Havana and his fishing boat
Up-close concerts with some of the best living jazz artists in the world
Optional cave swimming
Apothecary Museum
Stunning beaches
Visit Al Capone’s historic home
See the historic DuPont Mansion
Afro-Cuban folkloric dance show
Salsa dancing
Waterfall hike and birdwatching
Beach time and shopping opportunities
Cienfuegos Botanical Gardens
Tour of Korimikao, school for the arts, with chances to interact with local artists and dancers
Roadside snorkeling, expect to see 12+ fish species in 5 feet of water!
Accessibility: Please note that in Cuba, the sidewalks are often cracked and uneven, tour members must be able to handle walking on uneven terrain. You must be able to walk up to 3 miles a day to participate in the tour.
Day 1: Welcome to Cuba!
Arrive in Havana.
You’ll receive a warm greeting from our team at the airport and take you to get settled at the casa particular (Cuban B&B) in Havana. Then we’ll head out for a welcome dinner at our favorite paladar (privately-owned restaurant) overlooking the nighttime Malecón. Afterwards, you might go to the Hotel Nacional to enjoy cigars on the patio with live music and hear stories of gambling and the mafia’s influence on Havana in the 1950’s.
Meals: Dinner
Day 2: Varadero
We’ll start the morning with an introduction to Havana, where we will spend the last four days of the tour. It’s a great opportunity to get a peek at it before the city gets filled with guests arriving for the Jazz Festival.
After the introductory tour, we’ll head towards the exquisite beach town of Varadero. Bring your swimsuit in your backpack because the drive north along the coast includes a great palace for refreshments and swimming in a large cave. We’ll also stop in Matanzas to visit an apothecary shop that has been well-preserved for the last century.
We’ll enjoy a sunset dinner in Varadero, a very walkable town. You may even choose a night out dancing at one of the beach clubs (particularly if you are a Beatles fan).
Meals: Breakfast, Dinner
Day 3: Varadero
This is a great day to explore Varadero. You’ll quickly see why it was an attractive place for Al Capone, the DuPont family and more in the 1940’s. You’ll get to learn about the town and its people, as well as enjoy some of the finest beaches in all of the Caribbean.
Meals: Breakfast, Dinner
Day 4: Trinidad
After breakfast, we will head through the citrus orchards south to Trinidad.
Arriving in Trinidad you discover another world. Trinidad is a cozy, bustling town of Cubans and tourists, with French and Spanish-inspired architecture, stories of slave trade and wealth in the heart of the sugar industry of Cuba. Roger will give us a walking tour to get our bearings, learn the stories, and enjoy lunch together. Trinidad’s cobblestone can be brutal on your feet, so be sure to have thick-soled walking shoes.
After some free time, we will head out to try our hands at dance. Get ready for salsa dance lessons, smiles, and laughter with vibrant young Cuban instructors. Dinner is on your own, and there are many excellent choices nearby. Live music is easily found on every corner, and this is the best city to take in an Afro-Cuban Yoruba Orisha dance and drumming performances. Meals: Breakfast
Day 5: Trinidad
We will start the day with a short drive to a nearby nature preserve, “El Cubano,” where we are likely to see many unique Cuban birds, particularly the national bird of Cuba, the Tocororo (Cuban Trogon) on our 2-3 hour hike to a gorgeous waterfall and swimming.
Back in town, enjoy meeting artists and seeing their work, particularly the reclaimed wooden shutters with carvings. A favorite lunch place you might consider is San Jose, which is known for its huge hamburgers and tasty, sweet plantains.
In the afternoon you’ll have time to explore more of the town, or join the group at the beach, where there are umbrellas, lounge chairs, and lovely soft sand. In the evening, dinner is on your own followed by live music at the outdoor amphitheater, the hub of the action in Trinidad. Stay up late tonight! Nightlife in Trinidad is probably the most accessible and intense in all of Cuba, with numerous live music venues and free dance performances in the town square.
Meals: Breakfast
Day 6: Trinidad to Cienfuegos
You’ll have time in the morning to do your last-minute shopping or photography in the sweet little town of Trinidad before we head west to Cienfuegos, just 50 miles away.
En route, we’ll stop at the Cienfuegos Botanical Gardens, established in 1901 and home to an incredible arboretum with many endemic species of plants.
Arriving in Cienfuegos we will do a city tour and have lunch. Cienfuegos has a population of 400,000 and was built 200 years after Trinidad. Historically, this was an important city. When American cruise ships could go to Cuba, this was a popular port. The downtown area is established as a UNESCO World Heritage site with beautiful French-inspired architecture from the early 19th century.
The Palacio del Valle (pictured) is an incredible place to take photos and hear of the family that had this Moroccan-style home built in Cuba.
Prepare for a delicious dinner tonight!
Meals: Breakfast, Lunch
Day 7: Cienfuegos to Havana
You may want to start the day with your swimsuit underneath your clothes! As we return to Havana, there is an amazing place to stop to swim in a cenote and snorkel in the ocean, with lots of fish just 15 feet from shore (you’ll be thankful for swim shoes here).
On our journey north, we will have lunch and visit an ornithologist’s home where you will observe the Bee Hummingbirds, endemic to Cuba and the smallest bird in the world. Also, meet the student dancers and musicians at Korimikao, the school of the arts. This sheds light on the value of dance, music, and visual arts in Cuban culture, rounding out some of our coming concerts.
Your time in the countryside is drawing to an end as you enter the bustling city, crumbling concrete, and fascinating architecture that encompasses Havana.
Rest on the bus as we drive so you’re ready for a night out at the Havana Jazz Festival!
Meals: Breakfast, Dinner
Day 8: Havana
Wear your walking shoes to start this day! We start with a ride in beautiful vintage cars through the city to the fishing village of Jaimanitas and the home of the famous artist Jose Fuster. Fuster has made his entire home, and much of the surrounding neighborhood, into an outdoor art gallery using tiles in mosaic forms. The driving tour in classic cars will take you to the forest of Havana, the famous Revolutionary Square, and through the gorgeous historic embassy neighborhoods. Our ride will end in the most historic areas of Havana and you’ll hear the stories dating back to the 16th and 17th centuries when this part of the city was established. Incredible architecture and photo opportunities abound!
In the late afternoon we will return to our casas for free time before dinner. After dinner, it’s another big night out at the Havana Jazz Festival.
Meals: Breakfast, Dinner
Be prepared: check out our list of recommended reading here
Day 9: Havana
Havana is known for the many haunts of Ernest Hemingway. Today we will head out to Finca Vigía, Hemingway’s home in the hills above Havana. It has been well maintained and shows his love of books, his writing “tower” and more. You’ll even see his fishing boat, Pilar, on display, no doubt part of the inspiration for The Old Man and the Sea. Lunch will be in the mellow fishing town of Cojimar, where he kept Pilar.
In the afternoon there will be time to roam Havana on your own or rest up for tonight’s performances! We will have a lovely farewell dinner before we go to our final show.
Meals: Breakfast, Lunch
Day 10: Departure
Treasure your final glimpses of the city as you head to the airport (2 hours prior to departure). Say goodbye to Roger and your driver. We hope you will return soon!
Meals: Breakfast
