A Unique Cuban Story

Cuba classic car and driver photo by Paula RoseckyFrom shopping with ration cards, to beach BBQs, to whooping it up with soul and jazz singers, our Unique Cuban Story gives you the opportunity to experience the real Cuba with amazing locals as our guides. Theywill show you the Cuba they love and the land that challenges them.

This is a people-to-people journey at its best, where our Cuban friends will share their stories and invite you to experience the culture, history, music and arts of the place they call home.

Crooked Trails friends in Cuba

Participants on this group travel program will be joined by a U.S.-based Crooked Trails guide under the People to People category of legal travel to Cuba.

Price Includes:
All accommodations in Casa Particulares (like B&Bs)
Meals as indicated in the itinerary (B, L, D)
All activities as listed in the itinerary
All in-country transportation
A Crooked Trails guide for the full journey
Donation to Crooked Trails projects 

Prices Does Not Include:
Alcoholic beverages
Gratuities for guides


Sample Itinerary

Our itineraries are designed to let the country and its people guide your experiences. Please be flexible and allow the program to unfold.

DAY 1 - Friday, September 28

Welcome to Havana, Cuba

Upon arrival, we'll be welcomed to Havana by our host and very good friend Mauricio. We will check into our rooms and then join Mauricio for a Cuban coffee on his terrace overlooking the Malecon and the ocean. Mauricio will share with us his wonderful wild stories of the city and his incredible life in Cuba.

After everyone arrives, we will experience Havana at a first glance while riding in our classic American convertible cars, cruising the Malecon and stopping for a drink on the terrace of the famous Art Deco Hotel Nacional de Cuba, the architectural beauty that has hosted everyone from Gary Cooper, Gabriela Garcia Marquez, Vladmir Putin and Jimmy Carter.

As the sun begins to set over the water, fisherman cast their lines, lovers embrace and we stroll off to a special welcome dinner together at a family home accompanied by music, stories and dancing. It's always a different experience, as we do not know who may show up.

After dinner, we will explore the different genres of Cuban music with our friend and famous Jazz singer, Meiby Bella, accompanying her to a local bar where she will sing for us and the crowd.

Overnight at the Casa Particular


DAY 2 - Saturday, September 29


Today, we will experience the colonial magnificence and funky art-filled alleys of Havana on foot. Check out the second-hand book market in the Plaza de Armas, browsing through classic and new books and an amazing variety of revolutionary propaganda posters from all over the world. Listen awhile to street musicians practicing and trying out new songs. Don't forget to stop for a Cuban pastry (pastele) and a strong sweet cup of coffee.

In the afternoon, we will visit Ernest Hemingway's house, as well as many of the bars he used to drink at all in a classic old American convertible car, just as he would. Exploring his life with a Cuban author and Hemingway aficionado, we will visit his old haunts and his home. The house, Finca Vigia (Lookout Farm), is located outside of Havana in the neighborhood of San Francisco de Paula, was Hemingway's longtime home away from home. This big limestone villa and thirteen acres of banana trees, tropical shrubs, and carefully tended gardens, stands much as he and his wife left it in 1960, when he returned to the States permanently. Currently a Cuban government museum, many of the locals who ran the place for "Papa" still live and work there, caring for the grounds and pointing the visitors to the pool where "Papa" swam, the big bedroom where he wrote, and the tall white tower lookout tower to stare from his heights over the trees and toward Havana. We finish our journey in the port side town of Cojimar where Hemingway moored his boat, “Pilar”. Cojimar is a very quaint little town that will provide a glimpse into the quiet life of Hemingway and is also the location of the old Spanish fort built in1649, presently operated by the Cuban Coast Guard.

Top the afternoon off with a salsa dance class and get ready for a night of dancing!

Overnight at the Casa Particular


DAY 3 - Sunday, September 30


We will relax with a quiet morning after our two full days of activities.

Around mid-morning, we will head to the Callejon de Hamel, a walking artists' street where followers of the Santeria religion spend their time creating art. On Sundays there is a festival with live music, drumming and dancing. This is a spectacular cultural experience and shouldn’t be missed! We will be accompanied by our good friend and Santerian who will share some insights into this Afrocuban religion.

In the afternoon visit one of Havana's oldest cigar factories and see the art of hand-rolling that has made Cuban cigars so spectacular. Afterward, we will visit the family home of one of the many women who work in the factory, learning first hand about this famous and expansive industry. There will be cigars for purchase directly from the family.

The rest of the afternoon is free to explore the city on your own. If you would like to add another classic Cuban institution to your day, we suggest a visit to the Havana Club Museum—a lively and delicious introduction to Cuba’s national drink! Opened in 2000 by Havana Club, Cuba’s most famous brand, the museum's displays guide us through the full rum-making process, from sugarcane harvests on large-scale plantations to the fermentation and final bottling.The tour includes a rum tasting of the seven-year-old Havana Club rum!

Overnight at the Casa Particular


DAY 4 - Monday, October 1


After breakfast at our Casa Particular we head out to the Pinar del Rio Province, west of Havana, to make our way to the tobacco-rich and picturesque town of Vinales.

En route, we will stop at the home of self-taught artist, Miguel Antonio Remedios. His wooden home is typical of this mountainous area in the west of the country,with palm-frond thatched roof. Ducking under the old oxen yoke hanging above the door, we will be welcome into his home and living museum and explore his works of art. Miguel has set up a studio and gallery as well as a friendly community space for teaching art classes and folkloric music to kids.  He has also opened a bakery and has future plans to dedicate part of his land to permaculture project.

After lunch with Miguel and his family, we will continue on to Vinales. Lush and deeply green, this UNESCO World Heritage site is arguably one of Cuba's best natural settings. Between long valleys and rocky landscapes, Viñales give us a true look into the rural life of a Cuban farmer. Farmers work in the fields with their oxen, preparing the land for the variety of fruits, vegetables, coffee and tobacco. Dotted with traditional single-story farmhouses and warm, friendly people, Viñales is the true heart of Cuba.

Arriving at our family homes, we will drop our things and head out to see our friend (and a real character!) Carlos, locally known as 'El Cowboy'. We will ride through the red clay paths of Vinales, around the limestone cliffs and tobacco fields, on horseback. El Cowboy will guide us through the land, sharing stories of his family and friends in the area who have worked these fields for a century. The afternoon light on the red hills, the countryside bars where we tie up our horses, and a personal class on how to roll the best handmade cigar from the best tobacco in all of Cuba, will fill our afternoon as we ride back to town as the sun sets over the hills behind us.

Returning to our family homes, we will learn the art of true Cuban cuisine with our friend Dunia, with an informal introduction to the dishes and flavors of Cuban home cooking.

For those feeling energetic, top off the evening at the local dance hall for music and a town show.

Overnight at the Casa Particular


DAY 5 - Tuesday, October 2


You will have the day to choose from a variety of activities, including relaxing at the family home, biking the surrounding valley, or walking to take in the amazing viewpoints. The hills around Vinales Valley are full of miradores (viewpoints) with long sweeping views of the limestone cliffs and tobacco fields. Rent a bike or hike on tree-lined paths to reach the best spots. Visit the botanical garden at the edge of town to learn about the cultivation of medical and ornamental plants as well as the native plant species.

Overnight at the Casa Particular


DAY 6 - Wednesday, October 3


Beach Day! Doing it local style, we will head to Cayo Jutias where local Cubans head to BBQ, play music and swim. The beach is a sight to be seen — leave the mainland and cross the water over a short causeway to Cayo Jutias, a tiny mangrove-covered island situated approximately 65km northwest of Vinales. This is Pinar del Rio's most 'undiscovered' beach, pure sand and water as far as the eye can see. Joined by local Vinales family, we will set up camp for a day for a BBQ, soaking up the sun, swimming and dancing as the sun sets over the water.

In the early evening, we will make our way to a nearby family home for a lovely home cooked meal and rest.


DAY 7 - Thursday, October 4


After breakfast at the casa particular, we head east towards toward the city of Matanzas. The drive today will take around four hours. Enjoy the beautiful scenery as we cross the southern tip of Havana and continue east. We will make some lovely stops along the way, including lunch.

In the afternoon we will arrive at La Cocicidencia. La Coincidencia Farm is the brainchild of Hector Correa, his wife Odalys, and their three children. Trained as an agronomist, Hector received his land from the Cuban government during their agricultural revival program. After working hard for 30 years, La Coincidence is now a permaculture haven! Hector's wife Odalys is an art historian who translates the land around her into art and expression. Under her influence, the farm is home to a ceramics and artist’s workshop. Currently, the farm grows native fruits and vegetables, along with legumes, sugar cane and honey. The farm also produces eggs, pork, poultry, beef and dairy. On this land, La Coincidencia supports three families and feeds and employs fifteen more families!

Dinner will be served, using only food from the surrounding land, including even the sugar and butter!

Overnight at a Casa Particular


DAY 8 - Friday, October 5


After breakfast at the casa particular, we will meet up with our guide and good friend, Evelyn, who will introduce us to the wonderful town of Matanzas. Evelyn's background in art history and personal interest in music and Santaria offers a special glimpse into the Matanzas' past as well as the vibrant present.

Often overlooked, Matanzas is a cultural gem. In the 18th and 19th centuries, the expansive trade of the port allowed this affluent town to develop rich literary and musical traditions, inspiring the nickname “the Athens of Cuba”. The large population of Afro-Cubans influenced the musical styles of danzón and rumba with drums and rhythms and developed distinct variations of the Santaria religion that are still practiced today. Boasting 17 bridges over three rivers, Matanzas is also known for poetry and theater, with performances produced in the 19th-century Sauto theater.

With Evelyn, we will be sure not to miss any of the best sites, including visits to the San Severino Castle (part of the "Slavery Path" project) and Finca Triunvirato (the site of one the most important slave revolts), as well as visiting a handmade book arts project and one of Cuba’s first and oldest pharmacies.

After lunch, we will visit the amazing arts workshop of the sculptor Lolo, where we will meet young and upcoming artists as well as established creators. In this intimate environment, we will learn about their techniques, their experiences and about art in general. We'll be able to discuss their art and their creative process with them as we explore. Not only can we see how the artists work, but we can get close to it, feel it and then create some of our own. We will receive a theoretical-practical class and an introduction to ceramics to be able to make a small piece with the artists.

We will return to Havana in the evening and check into our Casa Particular.

Overnight at the Casa Particular


DAY 9 - Saturday, October 6


Breakfast at the Casa Particular.

For those who are interested, today we will go back in time to learn the vibrant history of the founding of Havana, the colonial background and evolving design, both physically and politically, of the city. Then it will be brought to the present with the story and path of the Cuban Revolution on a guided tour through Havana.

Or, choose to enjoy some free time to explore on Havana on your own. We can give you many suggestions for wonderful places to visit and things to do!

In the evening we will gather together for a farewell dinner at one of Havana's most delicious paladars, San Cristobal, patronized by both the Obamas and by Mick Jagger!

For those who are still feeling energetic, we recommend a visit to the Fabrica del Arte Cubano. Is it an art gallery? Is it a restaurant? Is it a dance club? Yes to all above! The Fabrica del Arte Cubano is not to be missed. Find out what’s new and interesting in the art scene, grab a meal or drink at El Cocinero and dance a little. You shouldn't miss it!


DAY 10 - Sunday, October 7

Havana - Departure

Breakfast at the Casa Particular

On our last day in Cuba, we will embark on a morning visit with our friend Mauricio to the artistic creation of Fusterlandia, a fascinating project of mosaics that is the dream of the Cuban artist José Fuster. Compared to surrealist artists such as Picasso, Gaudí, Gauguin and Wifredo Lam, Fuster uses bright colors and simple shapes to create whimsical worlds and fantastical creatures.

In 1975, with the idea of large-scale public art in his mind, Fuster moved into the dilapidated neighborhood of Jaimanitas and began to decorate his home studio in his unique style of colorful mosaics. Soon the art began to extend over the walls and barriers of his house, and into and around his neighbors' land. His project grew like ceramic ivy and within a decade, nearby bus stops, doctor's offices, public fountains, benches and dividing walls were illustrated with his designs. Today, the neighborhood stands as an ever-evolving living kaleidoscope of art.

Return to the Casa Particular to pack up and head to the airport for an early afternoon flight home.





10D / 9N


September 28 - October 7, 2018




Havana - Vinales - Matanzas - Havana


Open-enrollment guided group program


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