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.

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Cuba Escapes

Choose your dates of a 5 day adventure

September thru March

Experience a private long weekend on one of our 5 day-trips to Santiago de Cuba or Havana.

Starting at $1,995

Full Itineraries


Past, Present & Future

October 25 - November 4, 2018

Travel the full extent of Cuba from the east, to the splendor of Havana and the lively colonial towns of Trinidad and Cienfuegos.


Full Itinerary

Behind the Headlines

 February 9 - 16, 2019

Join Cross Cultural Journeys and Charles (Chip) Barclay, recently retired foreign service officer, formerly posted in Havana on a more upscale adventure to Havana, Trinidad and Cienfuegos.


Full itinerary


Havana Jazz Fest
with Roger Glenn

January 16 - 21, 2019
from $3,995 

A historical and cultural journey from the rural roots of Cuban music to the International Jazz Festival in Havana, with jazz master Roger Glenn.

Full Itinerary 

Private Journeys 

 Choose your Dates 

An example of a Private Journey to Cuba with a focus on Culture, Music and Nature, or build your own Cuban adventure.

Choose your dates

Private Cuba

The Musical Heart of Cuba

Make it a private tour of 10 or more! Explore music, dance and art of Cuba with renowned percussionist and long-time Cuba expert, Carole Steele.

Choose your dates

Full itinerary

 Previous Trips


Music & Photography with Taj Mahal and Linda Wolf

Exploring the colorful, vibrant music and culture of Cuba in an intimate setting, with a world-renowned Blues musician


Culture and Yoga Immersion with Seane Corn

Inner Journey. Outer Adventure. Nurture an intimate, dynamic exchange with the people and places of Cuba, with daily yoga practice lead by internationally celebrated yoga instructor

Motorcycle Diaries with Christopher P. Baker

Join moto-journalist and travel expert Christopher Baker on a journey exploring Western and Central Cuba.

Our Team is Here to Help

Call: (800) 353-2276

 321 High School Rd, Suite D3, Box 353, Bainbridge Island, WA 98110