Havana Jazz Festival and More (Private Tour)

Check out this 2022 Festival news clip.


What is included:

  • Travel licenses, mandatory Cuban health insurance, and visas
  • 9 nights in Cuban Bed and Breakfasts (casas particulares)
  • 17 meals and private, air-conditioned ground transportation
  • The best of Havana’s Annual Jazz Festival!
  • Purified water is always available
  • Curious About Cuba educational program
    (two 4 hour sessions of instruction provided before the trip, or access to the recording if you are unable to attend)

Cost: $2695 (market value $5195)
*Early Bird registrations 4 months prior to departure receive $200 discount

Deposit: $500 to reserve your spot

Payment 1: $1097.50 payment

Payment 2: $1097.50 payment due (+$500 for a single supplement)

Flight costs are on your own. We recommend purchase 8-12 weeks before departure, and we will provide recommendations for you.

Detailed itinerary:

The Annual Havana Jazz Festival was online, but now it’s back! Enjoy musicians from 9+ countries in this stellar event.

Additionally, you’ll get out of the big city to experience the best of Cuban UNESCO World Heritage sites, waterfalls, ocean views, bird-watching, Cuban food, architecture, and Cuban friends who await you on this phenomenal tour!  

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.

Day 1: Welcome to Cuba!  

Roger, our guide will pick you up at the airport and take you to get settled at the casa particular in Havana.  Then we’ll head out for a welcome dinner at our favorite paladar (privately-owned restaurant) overlooking the nighttime malecón.  For those that are ambitious, 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 in Havana in the 1950’s.   Meals: Dinner


Day 2: Havana

Havana Jazz Festival OPENING GALA happens tonight! Get ready to soak it all in! 

 Wear your walking shoes to start this day! We start with a visit to Fusterlandia in 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.  A Havana driving tour in classic cars will take you to the forest of Havana, the famous Revolutionary Square and through the gorgeous historic embassy neighborhoods.

The activities will be followed by lunch and exploring the neighborhood. In the late afternoon we will return to our casa particulares for free time and before returning to the old city at night for dinner at Doña Eutimia, a cozy paladar with tasty seafood and other offerings.

Havana Jazz Festival utilizes various venues throughout the city, including Mella Theatre, Sevilla Hotel, Karl Marx Theatre, and the National Theatre of Cuba.  We’ll go from dinner to one of the performances.  Meals: Breakfast, Dinner

Day 3: 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 concerts!  Meals: Breakfast, Lunch

Day 4: Havana

We will start the day with a walking tour of Old Havana City.  Among the fortresses and colonial archetecture, you’ll see Cathedral Plaza, built in the 18th-century Cuban baroque-style with its curves and flourishes above the doors and windows. If you look closely your see it was made of locally quarried limestone and is embedded with coral fossils and seashells.

You’ll see the sand mural and hear the stories of the historic plazas and the difference purposes they served.  There are lots of shops to peek into and great places to rest over a cup of coffee.

After lunch we will tour the Museum of the Revolution, which was once the “White House” of Cuba’s presidents before Castro.  Notice the bullet holes that have been preserved in the marble, as well as see the Granma boat and other artifacts from Castro’s revolution.  Enjoy some rest time before we head out for our final night of concerts at the Jazz Fest.  Meals: Breakfast, Dinner

Day 5: Varadero (2 hours driving)

After an hour exploring a final spot in Havana, we’ll depart the big city for a coastal drive to the exquisite beach town of Varadero. We’ll stop in Matanzas for lunch and visit the historic apothocary shop and hear about the family that ran the shop that has maintained much of it’s 19th century charm and incredible mohagony.

Arriving in Varadero, you’ll quickly see why it was an attractive place for Al Capone, the DuPont family and more in in the 1940’s. There will be free time before dinner for sunset, and a night out dancing at one of the beach clubs if you choose (particularly if you were a Beetles fan).  Meals: Breakfast, Dinner

 Day 6: Varadero to Trinidad (4 hours driving with stops)

We’ll finish the tour of Varadero in the morning, hearing it’s stories and legacy, and then 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 south 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, be sure to have thick-soled walking shoes.  You are always welcome to hire a pedi-cab to drive you through the streets of Trinidad when your feet grow weary.

After some free time,  we will head out 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 a Afro-Cuban Yorùbá Orisha dance and drumming performance.  Meals: Breakfast

Day 7: 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 Trogan).

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 it’s huge hamburgers, tasty sweet plantains, and remnants from the history of slave trade in Trinidad.

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.  You will have the chance to see Afro-Cuban folkloric dances performed in one of the many plazas.  Meals: Breakfast


Day 8: Trinidad to Cienfuegos (2 hours)

After breakfast and final morning photography or shopping for paintings, we will head to Cienfuegos, “The Pearl of the South”.  The is a popular stop for cruise ships due to it’s deep harbor.  Although it’s only 100 miles from Trinidad, this town was primarily settled 300 years later.  The main plaza is very picturesque, one of the UNESCO World Heritage sites we visit on the tour.  Be sure to explore the Spanish-Moorish inspired Palacio del Valle, where a cocktail is included in your admission.  Have some rest time before heading out for dinner.  Meals: Breakfast, Lunch


Day 9: Cienfuegos to Havana (4 hours with stops)

If you are an early riser, join the others in a visit to the Guanaroca Lagoon Nature Reserve.  A short walk from the entrance will take you to the lagoon where locals will paddle you in a boat across to lagoon. Plan to see the flamingos that migrate to the area from Florida and many other species of birds.

After the nature reserve, we will start the journey to the north coast.  En route, we drive along the picturesque Bay of Pigs where today there is a museum that recounts the events of this conflict.  The simple museum provides a fascinating overview of Cuba before Castro’s revolution and the subsequent Bay of Pigs attack.

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, a visit to the lively Korimikao, school of the arts, will shed light to the value of dance, music, and visual arts in Cuban culture.

Your time in the countryside is drawing to an end as you enter the bustling city, crumbling concrete, and fascinating architecture that encompasses Havana.  We will drive along the malecón and see the El Morro fortress en route to the final casas of the trip.  After some rest time, we will head out for dinner at a favorite spot on the malecón.



Day 10: Goodbye

Grasp 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


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