Cuban Woman Smoking giant cigarTravel to Cuba Has Never Been Easier on a Havana Day Trip!

Only 90 miles from Key West (50-minute flight).

On this one-of-a-kind Havana Day Trip, you will spend the day walking in the steps of Ernest Hemingway. Join our guided groups as we explore the cultural and historical connections between Cuba & Key West. Your trip will support the Cuban people’s newfound entrepreneurial spirit.

View Itinerary & Cancelation Policy

Havana Day Trip FAQ



7:00am – Check-in at Key West Airport

8:00am – 50 Minute Flight to Havana

9:00am – Clear Customs and start your Havana adventure

9:30am – Your Havana Excursion begins with a trip to Ernest Hemingway’s home in Cuba known as Finca Vigía in San Francisco de Paula Ward in Havana, Cuba. Finca Vigía, and Hemingway’s Key West home, are now museums. In addition, will see Hemingway’s famous fishing boat, El Pilar.

12:00pm – Lunch at an authentic Cuban restaurant.

1:30 pm: After lunch, you will head to Old Havana for a walking tour. Our Old Havana walking tour brings the city to life, allowing you to be swept up in all that this vibrant city has to offer. The city offers an unrivaled sensory experience that you will always remember! You will walk the sun-drenched cobblestone streets as you take in the oldest square in Havana (Plaza de Armas), which includes the oldest cathedral in the Western Hemisphere. Next, we follow in the footsteps of American literary icon Ernest Hemingway, making 3 stops that were Hemingway favorites: La Bodeguita (café), the Ambos Mundos (Hotel), & El Floridita Bar (the birthplace of the Daiquiri).

5:00pm – Return to the Havana Airport.

7:00pm – Arrive back in Key West.

*Please note that the Havana Day Trip itinerary may incur changes due to unforeseen circumstances.

hemingway in Cubaclassic car in havana


  • Price: $1195 per person. This includes airfare, visas, ground transportation in Cuba, local guide (meets you at airport), all taxes, tour & entry fees.
  • Day trips leave on Tuesdays and Fridays.
  • Havana Day Trips require 48 hour advance reservations. In winter months, we recommend reserving 6–8 weeks in advance.
  • A copy of your passport will be required to obtain a visa.
  • ESTA VISA holders are not eligible for travel to Cuba from the USA, and would not be able to go on the Havana Day Trip. Standard VISA holders are eligible for travel.
  • Small group, all-day guided tour.
  • In Havana, the tour uses private ground transportation.
  • Havana Day Trips use a small, Key West based aircraft that carries less than 10 passengers.
  • Our Aircraft: Britten-Norman BN2T Turbine Islander

In partnership with Air Key West, OurKeyWest develops and markets Cuban Cultural & Educational Experiences with the aim of supporting the Cuban people by providing technical business assistance to Cuban entrepreneurs and by creating a market to which Private Cuban Citizens can sell their goods and services. Our efforts are intended to promote independent activity and strengthen civil society in Cuba, as our guests maintain a full-time educational schedule that includes meaningful interaction with Cuban individuals.

cuban art