Take a journey of a lifetime and discover Cuba! Its people, rich history and vibrant culture offer you a once-in-a-lifetime journey. Since 1998, Cross Cultural Journeys has offered legal People-to-People experiences in Cuba. During this time we have built meaningful relationships with local organizations, NGOs (non-governmental organizations) artists, musicians, entrepreneurs, doctors, architects and everyday citizens. We draw upon these relationships to make your trip extraordinary.

CUBA: Havana Jazz Festival
January 22 - 29, 2023
Havana, Matanzas

Held annually since 1979, Havana Jazz Festival is a six-day feast of spellbinding performances by some of the best musicians in the world! 

Meet local musicians and artists as you take in the historical and cultural wonders of Havana, Cuba's gritty, bustling capital. Visit Matanzas, the nearby port city known as the birthplace of the Rumba and Danzón. You’ll fall in love with elegant, exuberant Havana: its friendly residents, contemporary artists, exceptional architecture, music, and colorful outdoor markets. Mingle with renowned musicians at local performances as you meet people who welcome visitors with friendly smiles, laughter and conversation.

CUBA: Havana Jazz Festival is run through the United States government OFAC general travel category Support for the Cuban People.

Verduras farm

CUBA: Life Behind the Headlines
Havana, Cienfuegos and Trinidad
May 13 - 20, 2023

Join  Cross Cultural Journeys, Journey Leader and former US diplomat in Cuba, Charles "Chip" Barclay on an exciting learning journey in Support of the Cuban People. Meet the Cuban artists in the charming colonial town of Cienfuegos, and spend time with well known, and also up-and-coming, contemporary artists in their studios in Trinidad.


Cuba and US flags

Cuba 5-day Escapes

Choose your dates of a 5 day adventure

Experience a private long weekend on one of our 5 day-trips to Havana; or the French Colonial town of Cienfuegos and Caribbean Trinidad.

4-10 travelers

5 Days to Havana or The Caribbean Coast



Private Journeys 

Choose your dates!

Come anytime on a Cultural Exchange and build your own Cuban adventure.

Private Cuba

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