Havana & Cuba Vacations, Trips, & Travel Itineraries | GeoEx

Cuba Insider

Explore the Island's Culture and Nature on a Custom Journey

Request Itinerary

Cuba Insider

Custom Travel | 5 Days
  • Enjoy insider access due to GeoEx’s long Cuba experience and connections
  • A 5- to 14-day journey built around your interests
  • Connect with Cuba’s residents and experts, exchanging ideas on the past, present, and future
  • Explore Havana, the Viñales Valley, and less-explored provinces
  • Be as active as you like: options for hiking, biking, and horseback riding

“Wandering Havana’s touristy old town and staring at old cars is one thing,” says Jennine Cohen, our chief Cuba expert, “but if you want private lessons and performances, time with emerging artists, and meetings with historians and economists, that’s another. The best restaurants in Cuba don’t have signage, and hotel options change constantly.” GeoEx began traveling to Cuba in 2000, and today we’ve got addresses and invitations that you won’t find in any guide book. Even more, our experienced guides skillfully make on-the-fly adjustments as things change. 

Trip Overview

It was wonderful to work with GeoEx in planning a tour to Cuba for our group of friends...GeoEx set up special visits with artists and musicians that matched our particular interests and created an itinerary that included the activities and pacing we wanted. It was such a treat to be in Cuba with our friends, and to have a trip designed specially for us.

– Susan G.

Art, Music, and Dance: Step into a new painter’s private studio and dialogue with an art historian and organizer of the country’s largest art event.

Spirituality: Learn about Cuba's Jewish history, as well as Santeria, the Afro-Caribbean religion which mingles Yoruba traditions with Roman Catholicism.

History, Architecture, and Economics: Gain an insider's perspectives on Cuban-American relations, the evolution of private enterprise, and the changing architectural landscape.

Nature, Agriculture, and Active Adventures: Walk with tobacco farmers and study conservation efforts with local scientists in a nature reserve. Get active with mountain biking, caving, snorkeling, and horseback riding.

Click below for more information or give our experts a call to learn what's possible.


GeoEx's Cuba Guides

Our trip leaders and guides have been taking people through Cuba for years. They understand the nuances of the place, are practiced at getting our guests into restaurants and other spots when other people can't, and are comfortable making on-the-fly adjustments as the country changes.

Find out more

Dates & Prices


Custom Trips offered November–May


Custom Trip: From $4,600 per person estimate based on two travelers, sharing a room on a 5-day itinerary; please call for individually tailored recommendations and pricing.


Prefer to join a small group trip? See our Connecting With Cuba's Living History itinerary.


  • Expertise of GeoEx’s travel specialists
  • Services of GeoEx’s in-house air reservations team
  • All accommodations
  • All ground transportation and airport transfers
  • Sightseeing, events, visits, and entrance fees
  • Most meals
  • Bottled water at included meals and while sightseeing
  • Services of local guides, drivers, and other staff
  • Some gratuities
  • Emergency evacuation services and secondary medical expense insurance

A Journey Built Just For You

Take customization to the next level on a journey fully tailored to you. GeoEx's destination specialists will gladly tailor this existing itinerary—or build one completely from scratch—to suit your style, interests, and time frame. Contact us to see what's possible.

Start The Conversation


Travel that Transforms

Read More
Road trip in Havana, Cuba

What to Know Before Going to Cuba

Read More
Tombs in the ancient Nabatean town of Hegra, also known as Madain Saleh, Saudi Arabia

Where GeoEx Travel Experts Are Dreaming of Going in 2021

Read More

Top Nine GeoEx Instagram Posts of 2019

Read More
Sigiriya Rock Fortress in Sri Lanka

When to Start Planning Your Trip

Read More
Local women in the Lawton neighborhood of Havana, Cuba

Why You Should Join an All-Women’s Cultural Trip to Cuba

Read More

Similar Trips

Colorful fruit sellers in Cartagena, Colombia

Flavors of Colombia

Learn More
Fisherman casting net on Irrawaddy River, Mandalay, Myanmar with GeoEx

Inner Burma

Learn More
Aerial view of downtown Havana, Cuba

Connecting with Cuba's Living History

Learn More

GeoEx eBook:
The Best of Wanderlust

An Anthology of Travel Stories
Edited by Don George