An alley in Havana, Cuba.

TWP Tours in Cuba

July 7 - 14, 2019

Join us for an adventure across Havana, Cienfuegos, and Trinidad as we learn about Cuban life, culture, and history from small business owners, rural families, artists, musicians, and the amazing people of Cuba.

One highlight will be a day spent with Teatro de los Elementos – a rural improvisational theater troupe living on a farm outside of Cienfuegos where TWP and Positive Legacy have helped support agroforestry and land restoration.

Trip Basics

Cost: $1,699 (Cost includes breakfasts and lunches, lodging, in-country transportation, park fees, and bilingual guides. Cost does not include airfare or cost of visas ~ $50.)

Length: 8 days

Lodging: Homestays and small private hotels

Weather: Hot and Humid – we’ll be in the tropics, in both urban and rural environments. Light rain showers may occur.

Difficulty: Mostly flat landscape, but lots of walking, especially in Havana. There are always taxis to opt out of walking, but costs may increase.

Want to join us in Cuba?

Register today!

Or contact Daniela Bueso at or call (970) 484-3678 ext 10

A picture of grafitti in Cuba.


This is a sample itinerary. Subject to change up until one month before departure.

Day One

Depart for Havana from Fort Lauderdale International Airport. After checking into the hotel in downtown Havana, you will enjoy an afternoon stroll down Paseo de Martí, where artists exhibit their products to the public. Enjoy cocktails in Habana Vieja (Old Havana), while discovering the beautiful 16th century architecture and fortification system that makes this city a UNESCO World Heritage Site. The evening will finish with dinner and entertainment at one of Havana's many premier music venues.

Day Two

The day will begin with a walking tour of beautiful Havana followed by a visit to Callejón de Hamel, the University of Havana, and the Malecón. In Callejón de Hamel, you will discover Havana's shrine to Afro-Cuban culture with vibrant artwork and spectacular rumba music that starts every Sunday at noon. Enjoy a delicious lunch at a local Paladar and then rest up before an evening of dinner and music at Zorra y Cuervo, Havana's most famous jazz club.

Day Three

Day three is a time to learn the ins and outs of social enterprises in Havana. We’ll meet with one of the professors that teaches Cuba’s fledgling entrepreneurs in how to manage their own business through the program "Cuba Emprende", since private enterprise laws loosened up in 2010. You will tour several small businesses and social enterprises in Havana, including a barbershop project, a print shop, and a small family-owned restaurant. Finish the evening at a local brew pub and get ready to travel in the morning.

Day Four

Visit the outskirts of Havana, where we’ll see the famed home of Ernest Hemingway, left just as he departed from it in 1960, after the Cuban Revolution. After that we’ll travel to the seaside town of Cojimar, where Hemingway found the inspiration for The Old Man and the Sea, and where we’ll enjoy a delectable seafood lunch. Afterward we’ll visit the famed Organopónico de Alamar, an organic urban farm that provides food and herbs to the surrounding urban markets, before heading back through the harbor tunnel to Havana.

Day Five

Travel to Cienfuegos on the shores of beautiful Bahiá de Cienfuegos. Enjoy a walking tour of the city where you can see it's colonial-era architecture and learn about the city's history. Enjoy lunch at a local cáfe, some free time to explore the city on your own, and then dinner and cultural activities to wrap up the day.

Day Six

Wake up and get ready to see what the community members of Cienfuegos are doing to protect their soils at a soil conservation project in Cumanayagua. Eat lunch at Jobero Verde, a local community project complete with an art gallery installation in the mountains and enjoy an improv theater presentation at Teatro de los Elementos, a Cuban theater company founded by José Oriol Gonzáles in 1990. Finish the day with dinner and cultural activities in town.

Day Seven

Pack up and spend the morning at the Cienfuegos Botanical Gardens. Tour the gardens and enjoy a light lunch before continuing to the magical city of Trinidad on the southern coast of Cuba. Check into the guest houses and take in the lively public squares, open bars and cafes that make this city such a wondrous, world-class destination.

Day Eight

Enjoy a free day walking the cobblestoned streets of this 500 year-old city and UNESCO World Heritage site. There are multiple local museums, dance studios, music venues, art studios, cafés, natural areas, and beaches worth exploring with other travelers. Rest up as you enjoy your final dinner in Cuba and some evening cultural activities.

Day Nine

Take the 2.5-hour drive to Santa Clara Airport and depart back to Fort Lauderdale International Airport.

Want to join us in Cuba?

Register today!

Or contact Daniela Bueso at or call (970) 484-3678 ext 10