Go now!  Time has stood still and it is magical.
— Stephanie P.
  • More about Your Oliver Guide: Stephanie Plexico

  • Trip Type: Couples

  • IDEAL TRIP length: Clearly, there is much more to see in Cuba, but you can experience the best of Havana in three days. Would add a day to see the beaches and hemingway's home.


The flight from Florida is an hour and customs is seamless in Havana. I looked into getting a driver to pick us up and there is no need to.  You can get a taxi right there and it is about $30 CPU. 30 minute drive to Havana. Change some money at the airport.  NO American dollars are allowed and credit cards are not accepted. The visa process is simple. Taxis are easy to find in Havana and it is a great walking city.


Hotel Saratoga: It is very central and the people that worked there were so nice.  We were very pleased. Side note: where Madonna, Beyonce & Jay Z stayed here. Casa Particulars or Home Stays are very popular and affordable.  It is a great way to get to know a family and experience authentic Cuban hospitality.

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  • La Guaridia: A restaurant in a beautiful dilapidated building, with a magical roof deck three stories up. Call (instead of email) to book a table. Madonna just had her birthday party here.

  • El Cocinero: In old power station, ask for rooftop lounge, cool place

  • Floridita: Home of the daiquiri and Ernest Hemingway’s local hangout

  • Rio Mar: Lunch

  • San Cristobal: Need to book

  • Hotel Nacional for the sunset and drinks

  • Many good restaurants – I would select ones that are on a roof deck, plaza or have live music.


  • Private walking tour of Old Havana: Hire a private guide because you learn so much from the guide’s own personal history and experience of life in Cuba. We used Fertours. We thought we would only want a 2-hour tour, but it turned out be a five-hour tour (including lunch), which was ideal, because there is so much to see and learn.
  • Museum of the Revolucion: housed in the former Presidential Palace. The exhibit provides a fascinating overview of the Revolution the Cuban government's perspective.
  • Cabaret-Tropicana.  Book in advance
  • Buena Vista Social Club
  • The National Ballet
  • Jazz Clubs

Saved for next time

  • La Fabrica de Arte Cubano (FAC, The Cuban Art Factory). Jazz, performance art space, gallery and disco all in one. Very sadly, FAC was closed when we were visiting.  I would be remiss to not include it, because it is supposed to be a phenomenal cultural experience and I plan to return to Havana to visit FAC.


  • The Cuban people are wonderful.  They are highly educated, thoughtful and curious to speak with tourists…take the time to get to know them and learn their wonderful history.
  • Watch Papa Hemingway in Cuba: It was the first Hollywood film to be filmed in Cuba since the 1959 revolution
  • Many of the sidewalks are cobblestone and are in disrepair, so you will want comfortable walking shoes.