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Trip Report

People-to-People Travel to Havana, Cuba

An incredible city stuck in time, Havana is a must-visit, as long as you plan in advance and get approval to travel there!

by dorritAbout Me:Writer and Brown University student who speaks English, Spanish, and French, and loves to travel! read more

North AmericaCuba5 days / April 2019

Highs & Lows

Day trip to Viñales Valley

Aeromexico told us there was not enough room for all of us on a returning flight we had booked months in advance.

Itinerary Overview

We arrived midday to Havana, were brought to Hotel Kempinski in the heart of Havana by a private driver, and had a refined dinner at Paladar Los Mercaderes. Complete with a city tour in an antique car, a revolution tour discussing the complex political past and present of the country, a trip to Hemingway's villa, and a day trip to the Vinales Valley, the following five days were full of an intimate look into the vibrant culture of Cuba, difficult discussions, and learning experiences. Each day of the trip had a different theme. We started with a tour of the old city, in a classic car. We spent an afternoon learning about the Jewish history and Jewish presence in Havana by visiting a synagogue and a Cuban Holocaust exhibit. The next day, our Hemingway tour brought us outside the city to Hemingway's villa, which has mostly been untouched since he left it in 1960. On our way back to the city, we stopped at Cojimar fishing village, the quaint small town that inspired Hemingway to write "The Old Man and the Sea." The next day we did a food tour, where we explored local markets with a paladar chef. He taught us how to make mojitos and cooked us a delicious lunch in his home. While we ate, professional Rumba dancers danced for us and taught us the technique. After lunch, we explored the studios of two local Cuban artists and then visited Museo de Bellas Artes. The next day was our incredible day trip to Vinales, where we went horseback riding with a guide through the countryside and learned about tobacco production. Our final day was a revolution tour, where we visited various Cuban monuments including Revolution Square, and we also got to step inside a bodega and learn about the ration system that is still in use today. 

  • 5 Nights: Havana
    To learn about the capital and its culture, history, and politics. And amazing food!
  • Day trip: Vinales
    To experience the countryside and learn about tobacco farming.
  • Day trip: Finca Vigía
    To experience the landscape inspiration for Hemingway's work

Q & A

  • What would you have changed?

    I would have loved to spent more time exploring Havana on my own time. If I could do it again, I would add a day or two.

  • Anything go wrong during the trip?

    Aeromexico completely screwed us over and told us when we arrived at the airport in Havana at 6 am, told us that they only had room for 3/6 of us on our flight, and the rest would have to leave on a flight leaving 12 hours later. The options for air travel to and from are very limited, so we just had to roll with it, but it ended up being quite the logistical nightmare.

  • Packing tips?

    It's very hot most of the year! Pack for warm weather, and nothing too flashy.

  • Transportation Tips?

    Best way to do it is with a private tour guide. We became very close with ours and are still in touch with him.

  • Booking details?

    Book through a travel agency. You'll need someone to help you get the right visa, and you need to have a detailed itinerary in order to get approval to enter the country.


  • Hotel Kempinski is in the heart of Havana's old city. Recently renovated, its accommodations are great. Due to the general situation in Cuba, wifi is hard to come by. While it was a pain to have to sign in and out of it all the time, it could have been a lot worse. Complimentary breakfast was provided. The quality of breakfast was mediocre; it is very difficult to get fresh produce in Cuba, so breakfast was lacking in that regard. But overall, everything was great, and the staff was friendly and very welcoming!