Cuba Trip Itinerary

(Sample 5 Day Aficionados Trip)

An Island steeped in history and tradition, Cuba has captured the imagination of Americans from Ernest Hemingway to today’s travelers. It is a land of natural beauty, smiling faces, powerful aromas and tastes.

By following the rules and guidance of our governments*, ECC has the rare opportunity to both experience and share our cultures while providing support to the Cuban people. Come take the journey and see this special place while we are able.

* ECC is licensed by the United States Treasury Department's Office of Foreign Assets Control (OFAC) to organize and conduct authorized group travel to Cuba. These trips engage participants in meaningful interactions with individuals in Cuba. LEARN MORE

Day 1: Arrival

From the airport we will travel to our lodgings in private homes to settle in and freshen up. 

The arrival dinner will be held at Havana’s most famous private restaurant. This restaurant demonstrates what amazing things can be accomplished when people have a strong enough desire to create something great despite tremendous odds against them. You will be able to enjoy our local Cuban guides conversation during dinner, after dinner, or both. 

After a long day, we will return to the homes for much deserved rest.

Day 2: History, Culture & Context

The day will begin with a traditional Cuban breakfast at the homes. Following breakfast we will make our way to Old Havana and the Museum of the Revolution to see ‘Fidel’s Boat’ Granma and some remnants of the Bay of Pigs invasion that the United States left in Cuba. 

From the museum, we will walk to Central Park and the 1950s American cars which will take us on a driving tour to see the farther flung monuments and sites of Havana. 

Lunch and conversation about what we have experienced so far will be enjoyed in one of Old Havana’s newer paladars which serves a Spanish influenced version of Cuban Cuisine. 

After lunch we will walk through the historic plazas with opportunities to take photos and experience some of the sites of what makes Old Havana an UNESCO World Heritage Site. This include but are not limited to the Cathedral Square, Old Plaza, and some of Ernest Hemingway’s old haunts.

One can enjoy a Daiquiri in El Floridita or a Mojito in the Bogedita del Medio as Papa used to. You are welcome to enjoy cigars during the majority of these activities.  

We will return to our homes to freshen up and then have a simple Cuban dinner at a Paladar in Old Havana. 

Day 3: Havana

After a hearty Cuban breakfast we will venture out to one of Havana’s operational cigar factories for a guided tour. We will be able to engage with the workers at the factory to exchange ideas and learn about their life as workers in Havana. 

After the factory tour, we will visit a cigar lounge and will have an opportunity to speak with local artists and artisans who create cigar humidors and items from wood and paintings. In the lounge we will enjoy lunch followed by a free afternoon. 

While at the lounge, ECC guides will be available to help you find addresses and transportation to whatever interests you in Havana. If you are not sure what to do, we will have some recommendations prepared for you including the arts and crafts market, shops selling items of interest to you, museums, and more. 

We will gather again at the hotel to go to dinner at a world renown restaurant with a cigar shop and indulgent traditional cuban cuisine.

Day 4: Tobacco Farm in Pinar del Rio

After a breakfast at the homes, we will head out to the ‘Mecca’ of tobacco, Pinar del Rio. We will spend time with a farmer who cultivates the leaves for the cigars rolled for Habanos. We will learn about the life of the tobacco farmer and eat lunch at the farm. There is much to see and experience at the farms. There are photos to take and if you want, cigars to taste. In the afternoon, we will return to Havana. 

For our farewell dinner we will enjoy a relaxed meal at a French inspired Cuban Paladar that is within walking distance to the hotel and will be a great place to enjoy dinner with a cigar.

Day 5: Departure

Breakfast at lodgings followed by briefing by ECC staff and private transfer to the airport for your return flight. Buen viaje!

WHAT’S INCLUDED

Once you arrive in Cuba, ECC will provide most of what you require including: 

  • All meals described in the itinerary

  • Lodging 

  • All gratuities at hotels and restaurants

  • Transportation to events and lodgings on the itinerary 

  • The cost of activities on the itinerary

  • Required Treasury Department documentation and administration

  • And documentation that you will retain post-trip

  • Expertise and services of our experienced Trip Leader and Guides 

“ECC would be honored to help you create a memorable travel experience to Cuba for you and your group. Please reach out to us and let us know how we can help today.”

- Colin Ganley (Founder - ECC)