Travel to Cuba Legally with Cultural Island Travel

Do you want to visit Havana but also have one day to escape to the countryside? Cultural Island Travel’s City and Countryside tour is perfect for you.

On this tour you will experience the old-world charm of Havana and the scenic rural areas of Pinar del Rio province, while enjoying the best music and art Cuba has to offer!

Tour Highlights: Old Havana walking tour, Hemingway house, tobacco farm, classic cars, food at Havana’s top paladares, and Havana’s famous nightlife!



5 days/4 nights

Our regular small group tours start very Friday but we also offer private tours to accommodate your travel dates. If you have different departure or return dates or for more information please call us at 1-800-494-1945 or email us at

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On our special tour you will meet Havana’s up-and-coming artists, as well as world famous painters. You will also be invited to attend exclusive dance performances, and listen to some of Cuba’s finest jazz, salsa bands as well as son bands in the style of the Buena Vista Social Club. You will also visit an incredible community project in the countryside and meet the farmers of Cuba’s famous cigar fields.

In Havana, you will feel like you are going back in time as you see the spectacular old American cars on the road and the fascinating old world architecture. In Piñar del Rio, you will travel to a scenic paradise to meet the farmers and experience an incredible community project. Our mission is to immerse you in this passionate culture to truly have you experience Cuba just like a local. “Support for the Cuban people” travel allows even the most seasoned travelers to view Cuba through the lens of the musicians, dancers and artists— an experience that is virtually impossible anywhere else in the world.  See our itinerary of hand picked experiences below: 


    Sample Itinerary

    DAY 1 Friday Havana

    • Check in for flight to Havana (Flight times vary)
    • Meet your tour leader at the arrival area
    • Visit the home of Ernest Hemingway: “Finca la Vigia”
    • Head to your lodging for check-in and orientation
    • Experience a classic convertible car ride through Havana City
    • Visit the famed Hotel Nacional
    • Nighttime suggestion: Enjoy a Buena Vista Club-style show at Cafe La Taberna

    DAY 2 Saturday Havana

    • Visit Old Havana and learn about Havana’s world-renowned UNESCO heritage designated architecture on an expertly guided walking tour (around 2 hours)
    • Visit the Taller de La Gráfica lithograph collective
    • Lunch at El Del Frente
    • Experience a private concert with a professional music group
    • Nighttime suggestion: Visit the Cuban Art Factory
    • Meals: Breakfast, Lunch

    DAY 3 Sunday Havana 

    • Visit the Bellas Artes Museum to see the best of Cuban Fine Arts
    • Lunch at Doña Eutemia paladar
    • Visit Fusterlandia, the home, gallery, and mosaic art neighborhood of Jose Fuster,
      sometimes referred to as the Picasso of the Caribbean
    • Experience a private concert with some of Cuba’s top young jazz artists
    • Meals: Breakfast, Lunch

    DAY 4 Monday Pinar Del Rio/Vinales Valley

    • Travel to the countryside
    • Meet a fourth generation farmer in Cuba’s famed tobacco fields
    • Enjoy a delicious organic lunch
    • Visit the community project “Patio Pelegrin,” often called the secret garden, which is not only an organic farm but also a community hub for dance, literature, debate, music, and theater for local residents to cultivate their artistic and intellectual interests.
    • Return to Havana
    • Meals: Breakfast, Lunch

    DAY 5 Tuesday Havana-United States 

    • Visit Havana’s markets (time permitting)
    • Check into your return flight
    • Adios Cuba!
    • Meals: Breakfast

    A Paladar is a privately owned restaurant, as opposed to regular restaurants that are owned and operated by the Cuban government. Paladares compete with each other and most of them are quite beautiful and creative with great food and flare. Eating at paladares also helps encourage private enterprise in Cuba. We include only paladares in our program to help local business and to provide you with the best Cuban culinary experience.

    What’s Included

    Included items in the price of your tour:
    • Cuban Visa (shipping included)
    • Roundtrip airport transfers
    • Daily breakfast in Cuba (at your accommodations)
    • All lunches during the tour at Cuba’s top paladares or privately run restaurants
    • All local air conditioned ground transportation during the tour
    • Pre-trip departure information on Cuba travel
    • Compliance with U.S. Treasury Department regulations
    • Superior accommodations
    • Expert CIT tour leader
    • Additional expert guides
    • Guaranteed small group size (no more than 8 people max)
    • Coordination of all listed activities on the itinerary and admission to those activities (this includes private music concerts, dance performances, artist visits, etc.)
    • Trip includes Havana and other cities depending on your tour
    • Concierge/reservation service for dinners and evening activities

    Not Included:

    • Round trip airfare
    • Dinner and after dinner activities
    • Tips for tour leaders, local guides, wait staff, and cleaning personnel
    • Luggage check in costs-please check with your particular airline for allowances

    Single Supplement: Varies depending on accommodations. If you do not see what you are looking for on this tour or any of our other scheduled tours please contact us for a custom tour quote.

    Tour Dates & Prices

    Departure Date
    Standard B&B
    Loft Habana
    Grand Aston La Habana
    Contact Us
    April 12, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    April 19, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    April 26, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    May 3, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    May 10, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    May 17, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    May 24, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    May 31, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    June 7, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    June 14, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    June 21, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    June 28, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    July 5, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    July 12, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    July 19, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    July 26, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    August 2, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    August 9, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    August 16, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    August 23, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    August 30, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    September 6, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    September 13, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    September 20, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    September 27, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    October 4, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    October 11, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    October 18, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    October 25, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    November 1, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    November 8, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    November 15, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    November 22, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    November 29, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    December 6, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    December 13, 2024 $2,280.00 $2,525.00 $2,685.00 Contact Us
    December 20, 2024 $2,480.00 $2,725.00 $2,885.00 Contact Us
    December 27, 2024 $2,480.00 $2,805.00 $2,885.00 Contact Us
    *Rates are based on double occupancy and per person. For single occupancy, group rates and more information please contact us.
    We also offer small group and referral discounts. Contact us   to speak with a representative today.

    Brochure & Top Cuba Tips

    Download our Cuba Tour Brochure and Top 10 Cuba Tips to get a better idea of what to expect when traveling to Cuba on an authentic CIT tour!


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