Cuba | Life Behind the Headlines


Join retired foreign service officer Charles (Chip) Barclay and Cuba guide Jesus Noguera 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.

Registration closing April 15

May 13-20, 2023

1 DOUBLE LEFT: $3,595/pp (double occupancy)

Single Supplement: $650

Cuba Guide:

Jesus Noguera Ravelo is a sought after Cuba guide based in Havana. A graduate of the Higher Institute for and International Relations (ISRI), he has over 20 years of experience in the field. Jesus has an untiring curiosity for the world. He speaks several languages and has visited over 30 countries worldwide. When he is not globe-trotting, or guiding international travelers around the hidden gems of Cuba, he resides in Centro Havana with his Cuban-Italian wife Daniela.

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. Between 2009 and late 2012 Barclay was Deputy Chief of Mission of the U.S. Interests Section in Havana, Cuba.  Barclay supervised the section’s human rights and refugee portfolio, consular operations, political and economic analysis and small law enforcement detail.


Itinerary highlights:

Day 1 | May 13 | Home City  > Havana 
Depending on arrival time we will take a panoramic drive through modern Havana in an American vintage car around some landmark areas, including the Revolution Square and the Malecon sea-front drive. We will finish at the workshop and home of renowned artist Jose Fuster who has turned his home in a mosaic wonderland with small colorful tiles adorning fountains, stairs, rooftops, benches and every other surface. A whole neighborhood turned into a masterpiece of tiles, turrets and, one might say “Gaudí-esque beauty”. Welcome dinner at La Guarida - on the top ten lists of local restaurants for Cuban and international cuisine. Don’t miss the roof top bar!
Havana Hotel

Day 2 | May 14 | Havana 
Walking tour of Old Havana. Visit all four squares in the oldest part of the city to witness the beauty of the historical buildings, sculptures and monuments. We will make special stops at the galleries and workshops of local artists. Late morning visit to Guámpara 165, the first independent production house and urban music label in Cuba. The project supports urban music, honoring the deep legacy of the African diaspora. In this multicultural and dynamic space several cultural expressions of a moving Cuba converge. Meet with Isnay Rodriguez, one of the three original founders to learn about the common history of some of the most popular Cuban and world music genres. Lunch on your own. Afternoon mob tour from a bygone era in Havana. Learn how the mob owned Cuba and then lost it to the Revolution. The tour will start in Centro Habana at the Hotel Sevilla where the mobsters established their headquarters during the prohibition and Al Capone lived in a suite. From the Hotel Sevilla we will go to Vedado neighborhood to visit two hotels; the Hotel Riviera owned by Mayer Lansky and the Capri owned by Santo Trafficante. We will finish our tour sipping a mojito at the bar of the Hotel Nacional de Cuba, where all leaders of US mafia went for a meeting in 1946. Happy Hour with cigar and rum tasting! A Sommelier and certified cigar quality control taster and Habanos Sommelier will teach us all about cigars; from the seed to the smoke through an interactive tasting and pairing. Non-smokers welcome to watch! Visit Fábrica de Arte Cubano, (FAC) a former century-old cooking-oil factory. An artist’s collective runs La Fábrica with permission from the government, which owns the building. Enjoy its art installations, photography exhibitions, music concerts and movies, in this spectacular venue. Part art exhibition and part community center, it also houses a gourmet restaurant, several coffee shops, and many bars. Dinner at Tierra Restaurant inside FAC.
Havana Hotel

Day 3 | May 15 | Havana 
Visit the home of Cuban American photographer Roberto Salas, who returned to Cuba from NY as a teenager returned to with his father right after the Revolution in 1959. He initially worked as a reporter for a newspaper in Havana, and then traveled abroad with Fidel Castro and took iconic photos of all Cuban leaders. He was later a war correspondent in Vietnam. Roberto is still an active photographer.
Visit the Cuban collection at National Museum of Fine Arts, a world class art and cultural center. The Palacio de Bellas Artes is a modernist edifice containing Cuban paintings, drawings and sculptures, its collection shows an excellent overview of Cuban nineteenth and twentieth century painting; culminating in some of the best of Cuban contemporary work, with regularly changing temporary exhibitions.
Visit the fishing village of Cojimar, six miles east of Havana, where Ernest Hemingway's boat Pilar was originally moored off the concrete dock below the old Spanish fort. Cojimar was the setting for many of Hemingway's stories, most notably The Old Man and the Sea. Locals erected an outdoor bust of the author just up the street from the restaurant La Terraza, a favorite hangout where we could go for a drink.
Lunch at Ajiaco Café Restaurant in Cojimar where we can enjoy Cuban dishes such as plantains filled with beef, Cuban “tamales”, and a mix of corn, taro and sweet potatoes fritters. Late afternoon visit to Finca Vigia, Ernest Hemingway's home, which today is an open air museum. The open windows and doorways afford cross views through most of the house —the interior is off-limits to visitors— and it appears as if Papa has just stepped away on a fishing trip. Dinner on your own.
Havana Hotel

Day 4 | May 16 | Havana
Visit to Callejón de Hamel, a vibrant “open air museum” and a community project created by artist Salvador Gonzalez. The murals and sculptures in this public space are devoted to Afro-Cuban culture, to divulge some of the symbols of cultures and religions of African origin, such as Santeria, Palo de Monte and the Abakua society. We will learn about the differences among the various African origin religions in Cuba. Late morning visit to the home of José (Pepe) Viera and Cecilia Bermudez for an overview on current Cuban life; social, political and economic changes currently happening. Pepe worked in the Cuban Mission to the UN, he was a Vice-Minister of Foreign Affairs, a lawyer, head of an investment firm and all-around intellectual; also a renowned expert on Cuban history and politics. Lunch with Pepe Viera and his wife Cecilia. Afternoon free to explore Havana on your own. Dinner on your own.
Havana Hotel


CIENFUEGOS | is a UNESCO World Heritage Site and a maritime city with a well preserved historic center. The city was founded as Fernandina de Jagua by French colonists coming from Louisiana in 1819 and renamed in 1829 after the Spanish governor Jose Cienfuegos.

TRINIDAD | founded in 1514 and by the early XIX century slave trade and sugar cane industry had a big boom bringing wealth to the region. The historical center of the town has not changed much over the last 150 years and many of its colonial buildings have been nicely restored.

Day 5 | May 17 | Havana > Cienfuegos > Trinidad
We depart early after breakfast and arrive in Cienfuegos to visit the city center. We will walk around the main square, the Cathedral church, the Terry Theatre and the Palacio del Valle building. Lunch included in Cienfuegos. Late afternoon arrival in Trinidad and check in to your hotel. Dinner on your own at a local paladar. Enjoy traditional music at the Casa de la Trova.
Sleep: Trinidad Hotel

Day 6 | May 18 | Trinidad
Early walking tour through the cobblestone streets of the old town Trinidad and stroll around Plaza Mayor to visit to museum Palacio Cantero, a well-preserved Spanish colonial mansion. Visit to local Farmers Market to buy food for our lunch, which we will cook together Cuban style! After a long leisurely lunch, we will enjoy a visit to a couple of local artist studios, such as Yudit Vidal and Jorge Cesar Saenz also Santander. Free time. If you are still hungry, dinner on your own. The evening is free to enjoy drinks and music at any of the many pleasant local establishments in Trinidad such as the Casa de la música or Casa de la Trova.
Sleep: Trinidad hotel (B/L)

Day 7 | May 19 | Havana
After breakfast, we drive back to Havana. Lunch on your own upon arrival. Free afternoon to explore and visit galleries and artists on your own. Farewell dinner at Restaurant San Cristobal, where President Obama and his family went for dinner on their first night in Havana. The restaurant is on the bottom floor of an early 20th century mansion. The food is Cuban creole: malanga, yucca, roast pork, lobster, fresh fish, shrimp and other traditional fare.
Havana Hotel (B/D)

Day 8 | May 20 | Havana > Home
Depart for Jose Martí Airport and our flights home.

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. Specific locations; accommodations and restaurants may change at the last minute in similar category, depending on Cuba and US restrictions, and the developing post-pandemic reopening of Cuba.

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, daily breakfast, meals as indicated "(B/L/D)"; Cuban English speaking local guide (Jesus Noguera); CCJ journey leader (Chip Barclay); guest speakers; all entrance fees on itinerary; preparation materials; tips for 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), and bellmen; optional gifts and artists supply items as gifts for Cubans; travel insurance.

Cross Cultural Journeys is not responsible for cancellation expenses that you might incur before or during our trip.  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.

May 13-20, 2023

STANDARD: $3,595 (double occupancy)
Single Supplement: $650

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