View of Trinidad Cuba

Cultural & Culinary Tour of Cuba in a Small Group

Our Cuban tour leader will introduce us to the fascinating culture of Cuba, and by staying in private guesthouses, you’ll have a chance to interact with Cubans in their own homes.  Cuba is changing fast, and we encourage you to visit it now, while it is still possible to savor the old history while relishing the new energy, including the food renaissance in Havana. Yes, it is legal for US citizens to travel to Cuba in a small group on a”support for the Cuban people” tour,  and our local connections will open up Cuba to you in all its glory and contradictions.

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Trip Length 9 Days
Walking Level Stroll
Trip Cost $2990

Walking Levels

Our walks are rated for their level of difficulty as follows:

  • Stroll – Daily distance of 2-5 km (1-3 miles) through archeological sites and in towns with stone stairways. Footwear: Lightweight walking shoes.
  • Easy – Daily distance of 8-10 km (5-7 miles) on dirt paths and gravel roads, with short ascents & descents. Good van access for assistance along the route. Footwear: Sturdy walking shoes.
  • Moderate – Daily distance of 12-16 km (8-10 miles) with longer ascents & descents. May include cobblestone paths and steps, or narrow paths along terraced hillsides. Some van access or options for shorter walks. Footwear: Sturdy walking shoes or lightweight boots.
  • Fitness – Daily distance of 12-16 km (8-10 miles) with steep ascents & descents. Walks are at altitudes of 1200-2450 meters (3500-8000 feet) on trails and forest service roads, some rocky or exposed sections. Limited van access, options for shorter or longer routes. Footwear: Lightweight boots.
Cuba capital with palm trees and pedestrians

A small group tour of Cuba with a maximum of 12 travelers is an ideal way to visit Cuba. This “support for the Cuban people” tour of western Cuba is conducted in English and is legal for US citizens, while all nationalities are welcome.

Trip Highlights

  • Tour colorful Havana with a local guide, and sip a refreshing daiquiri in Hemingway’s favorite bar
  • Learn the basic salsa moves with an experienced teacher, and never pass up a dance again
  • Meet a Cuban writer who discusses the political implications of a controlled press in today’s Cuba, with the opportunity to ask questions in an open forum
  • See how a talented Cuban artist supports a local daycare center and meet the street kids who learn to sing and dance at a community cultural center
  • Interact with Cubans in their homes by staying with them in casa particulares, and begin the day with a home-cooked breakfast

Trip Details

Jan 20-28, 2020

Hotel  in Havana

Hotel  in Havana

Single Supplement
$250 USD

Daily breakfast / 6 lunches / 6 dinners

Maximum Participants

Essential (rooms with bath in private homes, known as casa particulares)

Jump to Itinerary

Day-by-Day Itinerary

Explore Cuba Placeholder
Explore Cuba

Day One

Individual arrivals at Havana airport.  Transfer included to our lodging in a casa particular (4 nts.) Meet your Cuban guide and Italian Connection tour leader, followed by a welcome dinner.

Day Two

A walking tour with our Cuban guide will introduce you to the sights of Havana, with a stop for a refreshing daiquiri in Hemingway’s favorite bar, La Floridita.  In the afternoon, put on your dancing shoes as we learn to salsa with Havana’s coolest teachers.

Day Three

We head out of the city to the lush countryside at Las Terrazas, a pristine biosphere with traces of its history, today a rural community with a sustainable lifestyle. Take a short walk in the forest to spot the Cuban trogon, the national bird whose resplendent feathers mirror the colors of the Cuban flag. Meet the artist-in-residence in his lakeside studio before we enjoy a lunch of Cuban Creole specialties. Return to Havana and choose to dine in one of the city’s paladars, privately-run restaurants that are the vanguard of Havana’s culinary scene.

Day Four

Learn about Cuba’s educational system during a school visit, and explore the fascinating streets of Habana Vieja.  Meet a contemporary writer who defies the restrictions on free press as she exposes Cuba’s present day problems, and discuss the political implications of her writing during a question and answer session, a highlight of our people-to people tour. Tonight we indulge in a delicious meal of fresh fish and artfully combined spices at a lively paladar.

Day Five

An early departure from Havana has us heading to the lovely Playa Giron cove, where the failed Bay of Pigs invasion took place. Visit the nearby museum with powerful photos of Fidel Castro and the resistance movement.  Enjoy a short performance at a community center that helps young people find a direction in life through art, dance, and music.  Continue to the charming city of Cienfuegos, where we spend one night.

Day Six

After an orientation walk in the center of Cienfuegos, there is time to browse the handicraft market and admire the flower sellers’ stalls on the street corners.  Continue to Trinidad, where we stay 2 nights in family guesthouses, and immerse ourselves in Cuban culture.  After a short guided walk, you are free to scout out locales with live music, visit an artist’s studio, or just soak up the atmosphere of this colorful town.  Tonight we dine in the town’s best restaurant located in a former home, where a bed still sits in the middle of the dining room!

Day Seven

This morning we take a walk through quiet woodlands to a lovely waterfall, where the daring may take a swim in the refreshing cool water.  Meet a campesino, who lives in a simple wooden house and invites us to taste his herb tea made from wild plants that he harvests in the forest.  After a sumptuous buffet lunch, we’ll return to Trinidad for some free time, before heading to the beach for a sunset mojito.  Tonight’s dinner highlight is fresh grilled lobster, the house specialty.

Day Eight

We head to the provincial city of Santa Clara, where we visit a cigar factory, where Cuba’s finest tobacco is hand-rolled into the world’s most sought-after cigars.  Time to learn about the various brands with a cigar sommelier, before we head to the main park and check out what all the locals are up to.  Continue to Havana, for our last night in Cuba.  A special dinner and entertainment await us as we celebrate our in depth tour of western Cuba.

Day Nine

We can arrange taxis to the airport for return flights from Havana.

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Italian Connection

Italian Connection