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 [email protected]

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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. People-to- 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
  • Visit Fernando, the charismatic Cuban mechanic who specializes in the restoration
    of antique cars
  • 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. Treasure 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

Bed & Breakfast

4-Star Hotel

5 Star Hotel

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May 3, 2019
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May 10, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
May 17, 2019
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May 24, 2019
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May 31, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
June 7, 2019
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June 14, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
June 21, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
June 28, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
July 5, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
July 12, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
July 19, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
July 26, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
August 2, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
August 9, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
August 16, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
August 23, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
August 30, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
September 5, 2019
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September 13, 2019 $1,900.00 $2,120.00 $2,240.00 Contact Us
September 20, 2019 $1,900.00 $2,120.00 $2,240.00 Contact Us
September 27, 2019 $1,900.00 $2,120.00 $2,240.00 Contact Us
October 4, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
October 11, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
October 18, 2019 $1,900.00 $2,080.00 $2,240.00 Contact Us
October 25, 2019 $1,900.00 $2,080.00 $2,240.00 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!


Experience Cuba With Us

Legal, Safe, Unique Tours & Shore Excursions to Cuba! Call now and ask about our newly discounted rates for select tours!
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