After nearly half a century of limited relations between the U.S. and this island nation, Cuba is now open to visitors from the United States. The country continues to rapidly change with the influx of new visitors and political shifts, making travel easier in some ways and more complicated in others.

  • Perfect for
    Adventurers | Art Lovers | Families | Do Gooders | Intellectuals
  • When to go
    December-February | March-May
  • Ideal length of stay
    3-5 Nights

Designing Your Journey

Work with Indagare to design the perfect itinerary for an immersive journey. Our travel experts know the destination inside and out, and they can make recommendations based on your travel needs and preferences.

  • Three Days: Essential Havana- LP

    Three Days: Essential Havana

    To see the most authentic aspects of Havana, visitors must arrange special access tours with the best private guides, who can take you behind-the-scenes. Here is just one example of what our destination experts can create for you.


    • Day One: Old Havana

      From the airport and along the way into Havana, your guide will acquaint you with a few of the principal areas of the city, such as the Plaza de la Revolución and the Malecón. After lunch in a traditional paladar in Old Havana, you will have a walking tour of the beautiful colonial heart of the city, visiting the neighborhood’s numerous plazas and cathedrals. This evening, you will dine at an Indagare-adored restaurant and finish the night with a drink at a fun Latin jazz club in the Vedado neighborhood.

    • Day Two: Art in Havana

      Today, explore the relationship between Havana and the arts. Begin with a private visit to the Museo Nacional de Bellas Artes to see the Cuban art collection. Indagare can arrange for a local art historian to guide you through Cuba’s arts evolution since the colonial era. After lunch at a Vedado paladar, spend the afternoon visiting art galleries, printing workshops, art schools and meeting with artists in their studios. Have dinner at a hot spot restaurant, then head to Fábrica de Arte Cubano for live music and art exhibitions.

    • Day Three: History & Architecture

      Today, enjoy the splendor of 1950s Havana. Begin at the former home of Ernest Hemingway, Finca Vigía, then tour Cojimar, the village that inspired Hemingway’s novel The Old Man and the Sea. Have lunch in Cojimar, then return to Havana proper and tour the El Vedado and Miramar neighborhoods with a local architect. Depart your hotel in refurbished cars from the 1950s for dinner at a paladar in Miramar, then continue on to renowned cabaret Tropicana.

Where To Stay

We only feature hotels that we can vouch for first-hand. At many of them, Indagare members receive special perks, including upgrades, early check-in, spa credits, and more. Look for the Indagare Plus logo in the reviews.

Indagare's Amelia Osborne Scott
“The best parts of any Cuba trip are the personal interactions that you have with locals and specialists. My Insider Journey group’s favorite experience was having dinner with the CNN correspondent based in Havana and his Cuban-Panamanian wife who owns a shop in Miramar that sells handmade Cuban works.” Read the article
Ashley Dodgen-McCormick
“My family left Cuba shortly after the revolution in 1959, so my recent visit there was incredibly eye opening... Hearing the music in the streets, tasting the food and communicating with the local people was invigorating.” Read the article. 

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