Cuba 5 day holiday, footsteps of Hemingway

US $1845ToUS $2245 excluding flights
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5 Days
Tailor made
More info
Best suited to private groups of 2-6 people. Dates: Guaranteed departures for 2 or more people on any Sunday or Saturday! Please inquire today to begin the booking process. Tour is best for couples & private parties with small groups. Min age: 16.
Make enquiry

Description of Cuba 5 day holiday, footsteps of Hemingway

Price information

US $1845ToUS $2245 excluding flights
Convert currency:
Best suited to private groups of 2-6 people. Dates: Guaranteed departures for 2 or more people on any Sunday or Saturday! Please inquire today to begin the booking process. Tour is best for couples & private parties with small groups. Min age: 16.
Make enquiry

Departure information

This trip can be tailor made throughout the year to suit your requirements

Travel guides

US Citizens in Cuba
The advice for US citizens for visiting Cuba has changed slightly since the Biden administration took office. The situation around US travel to Cuba c...
Stepping into Havana for the first time is a world of classic cars, crackling transistor radios and clacking dominoes. As you meander into the country...

Responsible Travel

As the pioneers of responsible tourism, we've screened this (and every) holiday so that you can travel knowing it will help support the places and people that you visit, and the planet. Read how below.


This tour begins with the lead guide picking up all guests from the airport. We encourage all guests to get some similar flights so we can pick up everyone at the same time to avoid numerous cars being needed for transportation. We carpool our guests as often as possible to reduce our carbon footprint in Cuba.

When we are not driving classic Cuban cars on this tour, the majority of other activities consist of interacting with locals and exploring on foot. Walking allows us to slow down and explore things we stumble upon. We try to incorporate human powered activities into all of our Cuba itineraries.

Most of the accommodations on this tour consist of Casa Particulars, which are locally owned bed and breakfasts. This aligns with our purpose of travel to Cuba - to support the Cuban people. By staying in Casa Particulars we are putting money back into local families rather than large corporations taking up resources and money from the local communities.

On all of our packing lists for tours in Cuba, we recommend guests pack a water filtration device in an effort to reduce our use of single use plastic water bottles. Bringing along water filtration systems will allow our guests to drink available water without upsetting the stomach.

This tour also includes a visit to Viñales Valley. Viñales Valley is a spectacular area of the Cuban countryside where our guests meet with locals to learn about local agriculture, enjoy fresh produce, and learn how to help conserve the countryside and farmland of Cuba to support the local people.


On our Cuba trip we do a number of things which help to support the local communities there. These include - helping, consulting with and working personally with Cuban shops, services and individuals; sourcing materials and equipment in Cuba; encouraging, working with, and embracing Cuban people; treating our guests, partnerships, local communities and businesses fairly and justly; working with other partners and businesses who are passionate about giving back to the community and having our travelers stay at Casa Particular’s (modest family-run homestays).

Cuba is such a unique country, and US travelers must meet one of 11 different categories to visit the island legally. As a US-based operator, all of our guests must also meet one of the categories set in place by the United States. To meet the qualifications for Support for the Cuban People travel category as set forth by the United States government, each of our guests engage in a full-time schedule of activities that: enhance contact with the Cuban people, support civil society in Cuba, and/or promote the Cuban people's independence from Cuban authorities. This results in meaningful interaction with individuals in Cuba.
We utilize locally owned casa particulars (private homes, bed and breakfasts) and transport services, and patronize local restaurants called paladars. This helps keep operating costs benefiting the economies in which we operate.

After 5+ years of operation, we value the relationships with our local vendors and look forward to sending our guests into their caring services. We know the best people to recommend for any need, and have enjoyed years of happy guests and happy vendors.

On this tour, we eat many meals at paladars. Paladars are small, local, family-owned restaurants serving authentic Cuban food. We do this in effort to support the local community we are visiting and to give guests the opportunity to try a variety of local cuisine options, and to connect with the locals.

We are able to accommodate people with physical limitations, disabilities and medical conditions; please speak with our team ahead of time if you think you will require any additional assistance while on the trip.

All of our group tours in Cuba are LGBTQ+ friendly. Everyone is welcome on our tours regardless of identity.

We only employ Cubans and most of the time when visiting specific natural areas or cultural homages, we require a local expert guide to educate us on the area.

All of our operating staff and guides get paid at least minimum wage.

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