CUBA: Past, Present and Future | Resiliency Through the Decades

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CUBA: Resiliency through the Decades
November 10 - 18, 2022

Optional 3-night Viñales Valley Extension, November 18-22


SUSTAINING: $4,195 (1 double left)


$1,000/pp deposit due at the time of booking for all rate levels for CCJ's Cuba departures.

Single surcharge: $650

To send checks via mail (please do not write “Cuba” on your check as it may be held up in processing) make checks payable to: Cross Cultural Journeys, 321 Highschool Rd. NE, suite D3, box 353, Bainbridge Island, WA, 98110

Please note that the below itinerary is currently being updated.

Cuba: Resiliency Through the Decades  is a cross-country odyssey that spans the entire Cuban island from the Afro-Cuban and Tahíno Indian roots in the East, to Havana and Viñales Valley in the West!

We begin in Santiago de Cuba to learn about the signal events of the history of the Cuban revolution. Leap back in time to the remote, mountain-bound Baracoa, where Columbus first spotted Cuba and claimed it for the Spanish crown; visit the lonely train wreck where Che Guevara and his men blew up and broke the back of Batista’s defenses. In Havana, we visit artists and photographers in their studios and get a private guided tour of the Museum of Fine Arts, home of one of the most exquisite collections in Latin America. We learn about the past decade’s political and cultural changes to the Cuban economy, and and how the loosening of the US economic embargo during the Obama years led to an economic and cultural boom that lasted for only three years. The extended journey takes us to the less frequented lush Western part of Cuba, where tobacco and pineapple farms compete with stunning green hills in the dreamy landscape of Viñales Valley.

We will visit with Cubans in their kitchens and hear about how the ups and downs of the US-embargo and the Castro-regime have impacted their lives in direct and indirect ways. Last but not least, we will learn about the Cuban peoples’ difficult fight through the recent pandemic, and how finally a home-grown vaccine gave its’ people new hopes and dreams for a brighter future.

Cuba: Resiliency Through the Decades is run through the United States government OFAC general travel category Support for the Cuban People.

JOURNEY highlights

Day One: Arrive in Holguin
Day Two: Santiago de Cuba
Day Three: Santiago de Cuba
Day Four: Camagüey
Day Five: Trinidad
Day Six: Trinidad
Day Seven: Havana
Day Eight: Havana
Day Nine: Havana >> Home OR Viñales

Day Ten: Viñales
Day Eleven: Viñales
Day Twelve: Havana

Day Thirteen: Depart from Havana

  • Participate in private tours in Havana, Santiago and Viñales presented by well-known city architects and historians whose colorful presentations lay context for understanding five centuries in the development of Cuba’s most prominent cities
  • Meet with a variety of academics, local historians, architects, business owners, revolutionary photographers, geo-tourist experts, musicians, chefs, and local artisans in their galleries, homes, co-ops and street markets to view and discuss their professions
  • Gather for conversations with local musicians and international dance troupes, sharing and enjoying their music and performances at private studios, open venues and lively clubs
  • Dine in local paladars, small family-run restaurants licensed to provide meals in a private home and sample some of the best and most authentic food in Cuba as well as experience the intimate, warm spaces of local people
  • Experience life in a Kiribá Indian village, learning about the Taíno, the original indigenous inhabitants of Cuba and take a leisurely boat ride along the Tao River
  • Visit Cuba’s most historic places including the city of Guantanamo, the basilica of El Cobre, the Moncada Barracks, and José Martí’s burial site.
  • Enjoy private tours of the Museo de la Revolución housed in the former presidential palace, the Museo Nacional de Bellas Artes de La Habana (National Museum of Fine Arts of Havana).
  • Enjoy free time to discover the places and spaces most dear to the Cuban people with evenings open to visit cafes, nightly jazz clubs and other nighttime events.
  • Meet with Cuban health care workers to learn about how Cuba weathered the pandemic, and how the home-grown Cuban vaccine has brought the country, its’ people and economy back to life.

JOURNEY itinerary

SANTIAGO DE CUBA | Less visited by tourists, Santiago is the Cuba's second largest city and the capital of Oriente province, known for its stunning natural beauty. Santiago de Cuba is well known for its traditional dances, most notably son, from which salsa has been derived. The city celebrates Carnival in July, although it typically precedes Lent. With the city preoccupied with the holiday, Castro chose July 26 to enter undetected into the city to assault the Moncada Barracks. During Carnival, traditional conga music is played in the streets on a traditional pentatonic trumpet, called the trompeta china. A high number of residents of the city adhere to Afro-Cuban religions, most notably santería. The city hosts descendants of immigrants from the early 19th century from what is now Haiti. Some aspects of the religious "vodún" heritage of the city can be traced back to this community. Santiago de Cuba features several historic architectural styles, from Baroque to neoclassical. Many colonial buildings have huge windows and balconies, where people can enjoy views of the steep streets and wooded hills. Preserved historical treasures include the first Spanish dwelling in the Americas, the first cathedral in Cuba, Cobre mine, the first copper mine opened in the Americas; and the first Cuban museum.

Day 1 | November 10 | Home / Santiago de Cuba / Guantanamo Upon arrival in Cuba, you will meet your Cuban guide who will show you the small town of Siboney and the historical farm where Fidel Castro and his men gathered shortly before the attack on the Moncada Barracks, an event widely regarded as the beginning of the Cuban Revolution. Enjoy lunch on the small island of Cayo Granma, where red-capped houses rest upon stilts above the water guarding a traditional fishing community. After lunch, head towards our accommodation in Guantanamo, stopping to learn about the American occupation since 1903. Both the Cuban and US governments prohibit visiting the nearby US military base holding suspected al-Qaida terrorists. There will be time for questions and answers. In the town of Guantanamo we visit the dance group Ballet Folkloric, a local group performing Afro-Cuban dances and music. The group has been invited to perform in numerous international countries and venues. It is a spectacular production followed by questions and answers and conversation with the dancers. We then have a private concert of Changui music. This music is particular to the mountains in the area. Bring your dancing shoes! Upon arrival at the hotel, settle into your room and then join the rest of the group for dinner at a local paladar. Guantanamo Accommodation (L/D)

BARACOA | Located on the Eastern tip of the island, relishes in its isolated existence, away from the eyes of the rest of Cuba. This sort of geographical solitary confinement has lead to the city’s culturally unique characteristics and has preserved a very distinct way of Cuban life. In the early 19th century French planters crossed the waters from Haiti and began farming the local staples of coconut, cocoa and coffee in the mountains and the thriving economy began to slowly surface. Today, Baracoa enjoys a sleepy, rural Cuban life far removed from the more lively regions of the island.

Day 2 | November 11 | Baracoa Begin your first full day in Cuba with a drive along the eastern coastline to Baracoa, weaving in and out of Cuba’s tropical forest. In 1492 Columbus spotted the area from his ship and claimed Cuba for the Spanish crown. With a town center of quaint streets lined with red-tiled roofed colonial homes, many consider Baracoa to be Cuba's most enchanting Cuban town. In the 18th and 19th centuries, Baracoan settlers built three fortresses to protect the town from pirate attacks. El Castillo de Santa Bárbara, the oldest, sits high above the town, with splendid views of the bay and surrounding countryside. It has now been converted into a hotel with an absolutely beautiful view. For lunch, participate in a pig roast picnic at the El Carahual cacao plantation. After lunch, settle in and then set out to visit to the Casa de la Cultura, an art gallery where the director teaches art to local youth. If time permits, spend time at Galería de Arte Eliseo Osorio, an artist co-op featuring some of the best of Cuba woodcarvings. Dine on your own on local cuisine at a restaurant or beautiful paladar. A paladar is a small family-run restaurant licensed to provide meals in a private home. Here, you will taste some of the best food in Cuba as well as experience being in the intimate, warm spaces of local people. There is an optional visit to Casa de la Trova for music and dancing at the end of the evening.
Baracoa Accommodation (B/L)

Day 3 | November 12 | Baracoa After breakfast, explore the town with a local historian, discovering the places and spaces most dear to the Cuba people. Absorb your impressions of the tropical air, rhythm and color wafting out of the doorways you pass, laughter and conversation easily bouncing amongst neighbors, meeting local people along the way. After our time in the city, drive to a Kiribá Indian village to learn about the Taíno, the original indigenous inhabitants, from a well known Baracoa historian and author who will accompany our group. By the mid-sixteenth century, the village numbers had dropped to less than a few thousand as a result of disease, mass suicides and Spanish exploitation. After lunch take a boat ride along the Tao River to the location where two rivers come together. Here we will visit with the indigenous Indian inhabitants who live on the beachfront. There will be a dance performance, conversations and interaction with the village people. Dinner on your own at a local restaurant or paladar.
Baracoa Accommodation (B/L)

Day 4 | November 13 | Santiago After breakfast, drive back to Santiago, located along Cuba’s southeast coast. Today we will have the chance to explore this vibrant Caribbean city with a historic overview and slide presentation by a city architect and planner to help us understand the history and culture of Santiago. Santiago is the cradle of the Cuban revolution and one of the country’s most exotic and ethnically diverse cities. Upon arrival, visit the cemetery of Santa Ifigenia, where Cuba’s national hero, José Martí rests inside an impending mausoleum. Then, visit the Velazquez house for a guided tour of the oldest intact house in Cuba and the home of the first governor of Cuba in the 1500’s. Here we can envision what life was like at that time. After checking into our accommodation, we will gather for dinner at an outdoor restaurant.
Santiago Accommodation (B/L/D)

HAVANA | Situated only 90 miles off the shores of the Florida Keys, Havana is one of the most romantic and bustling cities of the Caribbean islands. The Malecón (waterfront) is washed day and night by the Atlantic Ocean's deep blue crushing waves. Next to the crumbling pastel facades, the sidewalks fill with young musicians and artists, and local Cubans on their way to and from work. All over town, you will find amazing small family run restaurants, and despite the country's limited resources, they are able to provide visitors with some of the most exquisite and creative cuisine of the region. Enjoy music and dance at local bars and clubs along the cobble stones streets in Old Town or at the Jazz and Blues clubs in Havana's Vedado district and Miramar neighborhoods.

Day 5 | November 14 | Havana After breakfast, depart on an early morning flight to Havana, Cuba’s capital city. Lunch on your own en route. Upon arrival, settle into our accommodation and rest for an afternoon meeting with a well-known expert on Cuban architecture and city planner. Enjoy a talk about the history of the city’s fascinating past and the outlook for the future. After our time discussing the history, art and culture of Havana enjoy dinner at the a nearby restaurant, and resting for your first full day in the capital city. Optional late night out at a local Jazz Club.
Havana Accommodation (B/D)

Day 6 | November 15 | Havana  Begin the day with a visit to Beatriz Santacana at Estudio Taller Santacana. You will have the ability to purchase her pieces directly from the artist. Late morning visit to Havana’s National Museum of Fine Arts, the Museo Nacional de Bellas Artes de La Habana, where a museum guide will share the history of Cuba through its impressive art history. For those interested, visit the Museo de la Revolución, the former Presidential Palace where students attempted to assassinate Batista in 1957. Enjoy lunch on your own with time to explore. In the mid-afternoon, attend a dance performance by Habana Compás with its unique fusion of flamenco and Afro-Cuban dance that is unique to anything else in Cuba. Enjoy the evening on your own for dinner and exploring the capital city. 
Havana Accommodation (B)

Day 7 | November 16 | Havana After an early breakfast, we will visit the historical memorial to José Martí at Plaza de la Revolución, Revolution Square, and give you a short driving tour to see the amazing architectural treasures in the Miramar neighborhood, followed by an intimate meeting with the world-renowned photographer Roberto Salas in his Miramar home. Salas’s photographs of Fidel Castro and Che Guevara are legendary. Together with his Cuban-born father, Osvaldo, he met Castro in 1955 and in 1959, following Castro's rise to power, they were invited by Castro himself to work for the government newspaper Revolución. Enjoy this in-home visit and hear about Havana through their eyes. Lunch at a Miramar paladar. After lunch visit the Muraleando Project and meet the students and teachers working in contemporary art. Late afternoon visit to the Havana artisan market for last minute shopping. Free evening and dinner on your own.
Havana Accommodation (B/L)

Day 8 | November 17 | Havana After breakfast, we drive to visit Finca Vigía, Ernest Hemingway’s primary residence from 1939 to 1960 for a guided tour. This is where Hemingway penned much of his classic “For Whom the Bell Tolls”. Lunch at a local paladar. We will stop for a visit at Colón Cemetary on the way back to our accommodation. On our last evening, we will take a drive in classic American cars along the Malecón and through the heart of Havana to our farewell dinner at La Guarida. Optional late night out at the Fabrica de Arte Cubano.
Havana Accommodation (B/L)

Day 9 | November 18 | Havana >> Home
Following breakfast, for those not extending their stay, we bid Cuba farewell as we transfer to the airport for our flights back home.



VIÑALES VALLEY | A Cuban gem! Well known for its many world famous Cuban tobacco plantations, this valley in the Sierra de Los Organos has a lush karst landscape surrounded by green rolling hills and mountains. The so called mogotes (limestone), tower around the valley, are one of the features that make the landscape of Valle de Viñales unique. Sprinkled with farms on fertile red soil it is suitable for all kinds of agriculture, where traditional methods and techniques are still used. The Valley is as UNESCO World Heritage Site and also a National Park.

Day 1 | November 18 | Havana >> Vñales Valley
For those staying for the extension, we continue our drive to Pinar del Rio and Viñales Valley. We will stop to visit some crystal caves on the way there. We continue to Viñales to check in to our accommodation. Afternoon free to explore Viñales (several activities to choose from, i.e. hiking; horseback riding; visit to pineapple farm; visit to tobacco farm; rock climbing; or zip-lining). Dinner included at Paladar el Olivo. Evening free to explore Viñales town.
Viñales Accomodation (B/D)  

Day 2 | November 19 | Viñales
After breakfast, your guide will accompany you to Viñales National Park, a green, dreamlike landscape, where you will stroll among giant limestone rocks unique to this area of Cuba. This day will include a light packed lunch (i.e. sandwiches or the like). Activities like first day in Viñales to be determined based on interest. Dinner on your own. Nighttime outing at Casa de la Musica.
Viñales Accomodation (B/L)

Day 3 | November 20 | Viñales / Las Terrazas / Havana
Free day to relax and explore Viñales Valley on your own. Meals on your own.
Viñales Accomodation (B)

Day 4 | November 21 | Viñales >> Havana
After breakfast, we check out of our casa particular and drive back to Havana. We will stop in Las Terrazas for a visit and following lunch at el Romero, one of Cuba’s only vegetarian restaurants. Free evening to explore. Dinner on your own.
Havana Accommodation (B/L)

November 22 | Havana Following breakfast, we bid Cuba farewell as we transfer to the airport for our flights back home. (B)

JOURNEY details:

NOTE: This itinerary might be subject to change to take advantage of the serendipity of the moment when in Cuba; to meet someone special, to engage in an activity that might occur unexpectedly, or to accommodate circumstances beyond our control. Restaurants or accommodations may change at the last minute in similar category.

FLIGHTS TO CUBA: Please note that as of April 2022, flights to Cuba from the United States only operate in and out of Jose Marti International airport in Havana. We expect this might change before our journey in November. We ask that you please hold off on booking your flight to Cuba until three months before departure, when we should have more information. If flights to the East of the island has resumed, we will ask travelers to book their Cuba bound flight into Holguín, and their home/US bound flight out of Havana. Several larger American carriers have service directly into Cuba from the United States. American Airlines, Jet Blue and United are the most frequent ones. You can book your air travel just as you book any other ticket online or use a regular travel agent to help you find a good deal. If you need assistance booking your air travel to Cuba, please contact our office and we will direct you to our partner travel agent.

ACCESSIBILITY and ACTIVITY LEVEL:  Moderate. This journey involves long days outdoors in the natural elements; city strolls on cobble stones streets and other uneven surfaces, and/or nature walks on uneven and sometimes steep surfaces. Travelers should feel comfortable walking for 1-3 hours per day, in a sunny and tropical/hot climate. Elevators may not be available in all locations, so participants should be able to climb several sets of stairs, sometimes without handrails. Concessions will be made to try and assist those who need more time. Some sites and locations are only accessible by foot.

See CCJ’s Cuba Destination Guide for more information regarding how to plan for your journey; food, drink, local weather, what to pack, etc.

INCLUDED: CCJ pre-departure itinerary/trip planning, Cuba Destination Guide (PDF document sent via email after final payment is received); registration and coordination; pre-departure meeting via Zoom (two - three weeks prior to departure); in country transportation per itinerary; one-way domestic flight between Santiago de Cuba and Havana; best available accommodation in boutique hotels or private homes in Havana (double occupancy); best available accommodation in boutique hotels or private homes outside Havana (double occupancy); daily breakfasts; lunches and dinners per itinerary (see “B/L/D”); Cuban English speaking local guide; CCJ trip manager; guest speakers; all entrance fees on itinerary; preparation materials; potable water on the bus/car (please bring a refillable water bottle to avoid single plastic use).

NOT INCLUDED: International airfare to/from Cuba; Cuban Visa/Entry Card (info will be sent upon registration); meals not on itinerary; alcoholic drinks; excursions not on the itinerary; tips for bellman and hotel staff (optional, yet customary); tips for local guide and driver (optional, yet customary); travel cancellation and evacuation insurance (strongly recommended, info will be sent upon registration).

Travel Protection and Medical Insurance
Cross Cultural Journeys is not responsible for cancellation expenses that you might incur before or during our trip. Cuba requires you to have a supplemental medical insurance plan apart from the basic plan that you will have attached to your Cuba bound flight. You may want to check first to see if your current insurance policy covers travel abroad, but we have found that most do not.

We strongly encourage considering taking out travel interruption and evacuation insurance to cover any emergencies abroad such as evacuation, or reimbursement for cancellation due to your own illness or an illness in your family. Some plans require you to take out this insurance within 21 days of your deposit to cover pre-existing conditions. CCJ has partnered with TravelSafe. You can visit our online portal to explore different plans. We encourage you to choose a plan covers travel interruption before you depart, as well as during the trip. CCJ is not responsible for events beyond our control in this regard.

Please visit the Cross Cultural Journeys - TravelSafe online portal to find a plan that works for you. You can also call TravelSafe directly at 1-800-523-8020. Make sure you mention that Cross Cultural Journeys is your tour operator to receive our special rates.

CUBA and COVID-19: As of April 4, 2022 the requirement for a negative PCR COVID test result has been eliminated as has the requirement to provide proof of full vaccination. As of May 31st, mask wearing is no longer obligatory, except in health facilities.
Note that these requirement as subject to change, and will be updated accordingly.


SUSTAINING: $4,195 (1 double left)


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