Travel to Cuba Legally with Cultural Island Travel

Join Cultural Island Travel in celebrating Havana’s 500th Anniversary


Enjoy a walking tour of Old Havana, ride in classic cars, tour the Cuban wing of the Fine Arts Museum, visit the Hemingway home, enjoy private concerts with top artists, dine at top paladares, and immerse yourself in this historic 500 year celebration of Havana!


5 days/4 nights

For more information please call us at 1-800-494-1945 or email us at

Viva La Habana!

On this tour you will get to experience all the best of Cuba’s capital city while also celebrating its quincentennial! Immerse yourself in Havana’s passionate music and dance scenes, meet local artists, learn about its rich history from experts, dine at top restaurants, ride in gorgeous classic cars – all during a historic celebration of the city. By traveling under Support for the Cuban People, you’ll not only visit Cuba’s most sought-after sites, you’ll meet the people who make this country so special. You’ll visit with artists and artisans, professional musicians, inspiring community projects and so much more.


Sample Itinerary

DAY 1 Friday, November 15, 2019 Havana

  • Check in for flight to Havana (Flight times vary)
  • Meet your tour leader at the arrival area
  • Visit Ernest Hemingway’s quirky estate on your way into Havana

Peek into the Cuban home of celebrated novelist Ernest Hemingway, where he wrote “The Old Man and the Sea” and “For Whom the Bell Tolls.” On this guided tour you will get a sense of the writer’s life in Havana and see his collection of books, trophies, and other memorabilia. Outside you will be able to view the gardens, pool, pet cemetery, and Hemingway’s boat, Pilar.

  • Welcome lunch at a top paladar (if flight arrives before noon)
  • Head to your lodging for check-in and orientation
  • Visit the historic Hotel Nacional and enjoy stunning views

The upscale Hotel Nacional is one of the country’s most famous landmarks, with a fascinating and storied history, ranging from a major mafia meeting in the ’40s that took place on-site to tunnels in the gardens used during the Cuban Missile Crisis. The common spaces, including the lobby and the ocean-view gardens, are gorgeous, casting light on Havana’s golden age of Cuban hospitality, nightlife and entertainment. Some past famous guests include Frank Sinatra, John Wayne, Winston Churchill, Mickey Mantle, and Marlon Brando!

  • Experience a ride in a classic convertible car around Havana City

Havana is beloved by American visitors with its collection of thousands of vintage American cars, manufactured before the Revolution and subsequent US embargo. In the absence of automobile imports, these living relics are preserved by Cuban mechanics or improvised fixes by the owners themselves. Experience an hour in a classic convertible Chevy, Ford or Oldsmobile!

  • Welcome dinner at Al Carbón paladar
  • Nighttime suggestion: Visit La Zorra y El Cuervo Jazz Club

DAY 2 Saturday, November 16, 2019 Havana

  • Happy 500th Havana!
  • Visit Old Havana and learn about Havana’s world-renowned UNESCO heritage designated architecture on an expertly guided walking tour (2 hrs)

There is no better introduction to Havana than a walk through Old Havana, where the streets are full of life – vendors, musicians, performance artists are everywhere. On this walk you will explore Old Havana’s five major plazas and see the interiors of cathedrals and other important buildings. UNESCO designated Old Havana as a world heritage site in 1982. Although today Havana is a sprawling metropolis of more than two million people, the old center retains an interesting mix of Baroque and neoclassical monuments, beautiful balconies and courtyards.

  • Visit the Taller de La Gráfica lithograph collective

Located in the heart of the old city, Taller de La Gráfica de la Habana is one of Havana’s most revered artistic attractions, featuring lithograph artists who create and sell their own experimental work on site. Visitors learn about the collective’s equipment and techniques from the artists themselves and can purchase art directly from the Taller.

  • Lunch at El del Frente paladar (a staff and client favorite, try the daiquiris!)
  • Experience a tour of the newly renovated and stunning Grand Theater of Havana

Named after Cuba’s most beloved ballerina, this gorgeous theater is the headquarters of the National Ballet and also features musicals, plays, and opera.

  • Havana 500 years celebration: Activities TBD
  • Nighttime suggestion: Enjoy a Buena Vista Social Club style-show at Café Taberna

On the corner of Plaza Vieja stands Cafe La Taberna, the city’s oldest music venue. Founded in 1772, hundreds of Cuba’s musical greats have passed through its doors, though it is most famously associated with mambo king Benny More. Soak in its history when you stop by for a traditional Cuban music show, offered every night at 9PM. Entrance fee includes three cocktails.

  • Meals: Breakfast, Lunch

DAY 3 Sunday, March 17, 2019 Havana 

  • Visit the Bellas Artes (Fine Arts) Museum with a private guide

Enjoy as an art expert guides you through the Cuban wing of this beautiful museum, providing rich historical detail and context. The displays are chronologically ordered, so you will be introduced to classic works such as La Gitana Tropical (The Tropical Gypsy) sometimes referred to as Cuba’s Mona Lisa, and then taken through a visual exploration of Cuban identity and political expression over the course of several galleries.

  • Lunch at La Guarida paladar (a celebrity favorite!)
  • Enjoy a performance by Habana Compás Dance troupe

Cuba’s Spanish and African roots are on display with this popular group, which merges flamenco style dance with Afro-Cuban rhythms. Dancers use sticks, castanets, heels, flip-flops, keys, chequerés and chairs to create a unique percussive aesthetic.

  • Visit Fernando, the charismatic Cuban mechanic who specializes in the restoration of antique cars

The Discovery Channel show “Cuban Chrome” is based on Fernando’s work and was the first US-based show to be filmed entirely in Cuba in recent years. He will give you a tour of his quirky workshop and take you for a spin in one of his antique cars!

  • Havana 500 years celebration: Activities TBD
  • Nighttime suggestion: Visit Fábrica de Arte Cubano

Havana’s hottest spot for nightlife, this converted warehouse features a four-story art gallery/film space with multiple stages for live music and outdoor/indoor bars.

  • Meals: Breakfast, Lunch

DAY 4 Monday, November 19, 2019 Havana

  • Visit the workshop of artisans who handcraft cigar humidors
  • Visit Fusterlandia, the home & gallery of José Fuster, the Picasso of the Caribbean

Inspired by works he saw by Gaudí in Spain and Brancusi in Romania, this self taught artist devoted himself to creating a more colorful and creative atmosphere for himself and his neighbors. The result is unlike anything you have ever seen!

  • Lunch at Fusterlandia
  • Havana 500 years celebration: Activities TBD
  • Visit the Tropicana nightclub for its world famous cabaret show
  • Meals: Breakfast, Lunch

DAY 5 Tuesday, November 19, 2019 Havana-United States 

  • Visit the San Jose craft market for final shopping (time permitting)

San José is the largest craft market in Havana, with more than 300 stalls offering all kinds of souvenirs: guayaberas, t-shirts, wooden sculptures, leather accessories, jewelry and artwork. Prices are negotiable, so bargaining with sellers becomes part of this unique experience.

  • Head to Jose Martí Airport for your return flight (airport transfer included)
  • 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

Contact Us

November 15-19, 2019 $2,320.00 $2,700.00 $2,860.00 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

Book by December 15 and get $200 off any of our full tour packages!
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