Join retired foreign service officer Charles (Chip) Barclay on a journey to explore the lesser-known aspects of Cuban life, and the personal stories behind the politics. Formerly the Deputy Chief of Mission at the U.S. Interests Section in Havana (now the U.S. Embassy), Chip will give you a rare insider's look behind the scenes at the fascinating political and economic changes taking place on the island.

2021 dates TBD


Single supplement: $650

Important notice about travel to Cuba after June 5th, 2019:

CUBA: Life Behind the Headlines is following the restrictions put forth by OFAC in June of 2019. It is administered under the general travel category “Support for the Cuban People”.
For questions related to Cross Cultural Journeys Cuba trips, or this itinerary, please contact CCJ President Cecilia Utne directly at 206-280-5360.

Daily Itinerary:


Day 1 | Home City  > Havana  Upon arrival in Havana, you are met by your Cuban guide. Travel half an hour to your conveniently located hotel. Walk to dinner and absorb your first impressions of the tropical air, rhythm and color wafting out of the doorways you pass, laughter and conversation bouncing amongst neighbors easily, meeting local people along the way. We dine at a local restaurant featuring traditional Cuban food and music. The music will follow us throughout our journey and is a window into the heart of Cuba.
Private Cuban Home / Casa Particular (D)



Day 2 | Havana After breakfast we begin our day with a talk on the city’s fascinating past and restoration plans, as told to us by an expert architect and city planner.  We learn about the restoration, which is necessary to provide housing for local inhabitants. Lunch will be in a restored colonial home overlooking the Plaza de Armas.  Street music and dancing celebrate the Cuban heritage of the people here. This afternoon spend time with printers at a printmaking co-op started 44 years ago by Che Guevera. Take time with the engravers to discuss their art and the life of artists in Cuba.  We will visit the Museo de Bellas Artes’ contemporary exhibition where your guide will explain the history of Cuba through its art.
Private Cuban Home / Casa Particular (B/L)


Day 3 | Havana Take the local ferry across to the island of Regla, where we visit the church of the Seafarers with the Black Madonna, their patron saint. You can talk with the Santeria priestesses outside the church, learning about the rich roots of an African tradition very much alive in Cuba and serving as a mainstay of faith in their everyday lives. Next we meet with local residents and spend time with the people who are working in a community to find local solutions to the scarcity challenges of food and water. The feeling of cooperation and ingenuity are palpable and many of the people you meet will surprise you with their multitude of talents, which they have had to develop to survive in a society lacking basic resources. Roof-top gardens, farming co-ops, bicycling, and sharing products and services are some signs you will see of how scarcity in Cuba has fostered individual ingenuity, with family support systems and neighbors binding closely together as a community. Dinner on your own at a local restaurant or paladar. We will provide a list of paladares and restaurants for you to try.  Cuba’s renowned paladars are small family-run restaurants 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, and real spaces of local people.
Private Cuban Home / Casa Particular  (B/L)


Day 4 | Havana / Santa Clara / Remedios After breakfast, leave for the province of Villa Clara. On the way (a three hour drive) there will be an opportunity to discuss a variety of topics with your Cuban guide en route. In Santa Clara, we explore the Tren Blindado (Armored Train), an important historical site where Che and Castro, along with the revolution army, defeated the Batista government. Also visit the Plaza de la Revolucion that is dominated by one of Cuba’s finest revolutionary statues, the giant figure of Che Guevara. Continue through the rural countryside to Remedios, a delightful settlement off the main tourist route which has retained its small town colonial charm.
Private Cuban Home / Casa Particular (B/L)

 Day 5 | Remedios Remedios was founded in 1578 and is considered one of the oldest settlements in the country. The historic city center was declared a National Historic Monument in 1980, and there are still Spanish colonial structures standing which date back to the seventeenth century. This colonial town is famous for its Christmas festivities, called parrandas, when two 'barrios' (El Carmen and San Salvador) compete the whole night to show the best fireworks. Meet with a local artist who will take you around town and introduce you to local people and projects where you will have an opportunity to engage in people to people exchanges.  After lunch at a local paladar we will visit a community youth project  “La Casa de la Ciudad”.  There will be a chance to take a private lesson to learn how to dance the salsa. This evening dinner is on your own to explore Remedios.

Private Cuban Home / Casa Particular  (B/L)


Day 6 | Remedios / Cienfuegos / Havana  After breakfast, you depart for Havana, stopping in French colonial Cienfuegos, to see the town and hear a nationally acclaimed local choir. Cienfuegos, the beloved city of Cuba, called “The Pearl the South” is known for its spacious, sea-misted streets and plazas. It is a relaxed city by the bay and is the only city in Cuba that was colonized by the French. The Bay of Cienfuegos was historically used as a refuge for ships during storms, now it is a shipping hub. Continuing on to Havana, you will stop for lunch along the way. Dinner is on your own. You may want to try La Guarida paladar, where the movie "Strawberry and Chocolate" was recorded, or Vista Mar, which has a sweeping view of the ocean. Both are in private homes.
Private Cuban Home / Casa Particular  (B/L)


Day 7 | Havana Visit ISA (Instituto Superior de Arte), where exceptional Cuban art students study painting, sculpture, pottery, music and arts communication for a full five years. We will spend time talking with the artists in their studios about their art and life in Cuba. Lunch is on your own for one last opportunity to try the local paladars with time to visit local markets and bazars. This afternoon will find us with a local guide at the Cemetario Colon, world re-known for its sculptures and burial site of numerous famous persons. Next, we visit artist Jose Fuster who has turned his neighborhood into a community of artistic. Gather this evening for a farewell dinner.
Private Cuban Home / Casa Particular  (B/D)


Day 8 | Havana/Home  Following breakfast, we bid Cuba farewell as we transfer to the airport for our flight home. (B)


Journey Details:

NOTE: This itinerary is subject to change to take advantage of the serendipity of the moment when we are in Cuba... to meet someone special, to engage in an activity that might occur unexpectedly, or to accommodate circumstances beyond our control. Restaurants or hotels may change in similar category.


INCLUDED: Itinerary for legal travel to Cuba under the “Support for the Cuban People” OFAC category of travel; in country transportation per itinerary; double occupancy in casa particular, full breakfast buffet daily at the hotel, plus one additional meal daily per itinerary (B/L/D); Cuban English speaking local guide; CCJ trip manager; guest speakers; all entrance fees on itinerary; preparation materials; tips for bellman and included meals on itinerary; bottled water on the bus.


NOT INCLUDED: International airfare; Cuba Entry Card (a.k.a. your ‘visa, information will be sent upon registration); alcoholic drinks; meals not on itinerary (B/L/D); excursions not on the itinerary; tips for local guide, and driver (optional, yet customary); optional gifts and artists supply items as gifts for Cubans; travel insurance.


For your convenience, we offer travel protection through Travelex Insurance Services. For more information on the recommended travel protection plans or to enroll, contact Travelex Insurance Services at 800-228-9792 and reference location number 47-0272.

Please advise Travelex that Cross Cultural Journeys is the travel company for this trip.

Upon request for enrollment Travelex will collect the following information for the traveler(s):

    1. Dates of travel
    2. Name of traveler
    3. Date of Birth
    4. Traveler’s phone number, address, city, state, zip
    5. Reason for travel: Support for the Cuban People
    6. Name of Travel Agency (Cross Cultural Journeys)

Please note: Insurance for this trip may differ from previous insurance purchases and follows a different process given the destination. In addition, this is a process we must follow as regulated by the Office of Foreign Asset Control for any travel to Cuba.

The product descriptions provided here are only brief summaries. The full coverage terms and details, including limitations and exclusions, are contained in the insurance policy. Travelex Insurance Services, Inc CA Agency License #0D10209. All products listed are underwritten by, Berkshire Hathaway Specialty Insurance Company, NAIC #22276. 11.17 Z7U


2021 dates TBD


Single supplement: $650

Journey Leader:

 Charles “Chip” Barclay was a Foreign Service officer with the U.S. Department of State for 28 years, serving in Europe, Latin America, Africa and Southeast Asia.  He is former State Department Spokesman for Western Hemisphere Affairs. Between 2009 and late 2012 Barclay was Deputy Chief of Mission of the U.S. Interests Section in Havana, Cuba.  Before diplomatic relations were resumed, the Interests Section consisted of approximately 50 American diplomats.  Barclay supervised the Section’s  human rights and refugee portfolio, Consular operations, political and economic analysis and small law enforcement detail.


Before his assignment in Cuba, he was Political Minister-Counselor for the U.S. Embassy in Mexico City.  Mr. Barclay has been a Public Affairs Officer in Malawi, Sarajevo and Kuala Lumpur and Deputy Chief of Mission Managua, Nicaragua.  He is currently an independent speaker on Cuba and teaches a course on global political issues at Cal Poly.



Chip Barclay photo
If you don't know José Martí, his face is everywhere in Cuba. He even beats "Che" Guevara in public tributes (statues, etc).
Hanging Out To Dry  II - Havana

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