Travel to Cuba Legally with Cultural Island Travel

Santiago is Cuba’s second largest city and former capital, and it has an incredibly rich history. It is the birthplace of Bacardi rum, conga lines, Revolutionary politics, son music, Cuban coffee; it is the site of Teddy Roosevelt’s famous Rough Riders’ crusade, and it is the hometown of some of Cuba’s most famous sons: Buena Vista Social Club singer Ibrahim Ferrer, and Desi Arnaz AKA Lucy’s husband “Ricky” from I Love Lucy, just to name a few!

Santiago also boasts a unique pan-Caribbean culture given its proximity to Haiti and Jamaica. French names are common, you might spot a Cuban rastafarian, and the cuisine is distinct. For a taste of local flavor try “pru” – a chai-like beverage that you won’t find anywhere else in Cuba!

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


Sample Itinerary

DAY 1 Friday Miami to Santiago de Cuba

  • Arrival at Santiago de Cuba, Antonio Maceo International Airport
  • Head to the lodging for check in and orientation
  • Nighttime suggestion: Enjoy legendary Son group Septeto Santiaguero

Septeto Santiaguero is a Cuban son group, deeply rooted in the traditional music from their hometown Santiago de Cuba, the cradle of son and bolero.

DAY 2 Saturday Santiago de Cuba

  • Enjoy a walking tour of Santiago de Cuba city and explore its historical plazas
  • Visit Museo “Casa de Diego Velázquez”

The oldest house still standing in Cuba, this early colonial abode dating from 1522 was the official residence of the island’s first governor, Diego Velazquez. Restored in the late 1960’s, the Andalusian-style facade with fine, wooden lattice windows was inaugurated in 1970 as a museum.

  • Lunch at Las Terrazas La Caridad paladar
  • Enjoy a performance by Compañía All Stars to learn about all of Cuba’s dances

The internationally acclaimed dance group, Compañia All Stars of Santiago de Cuba has toured Europe, Mexico, and the United States. They are known for their innovative choreography and incredible footwork.

  • Visit the Santiago de Cuba bay and enjoy the beauty of its new seafront

DAY 3 Sunday Santiago de Cuba

  • Visit Castillo del Morro

A UNESCO World Heritage Site since 1997, the San Pedro fort sits at the entrance of the Santiago Harbor, a few miles from the city center.  The breathtaking views from the upper terrace showcase Santiago’s coastline backed by majestic Sierra Maestra.

  • Visit Museo de Bacardi

Santiago’s most interesting museum, it was founded in 1899 by Emilio Bacardi Moreau, a Cuban writer and the first mayor of Santiago. He is more famous for his Caney Rum distillery, which was moved to Puerto Rico after the Revolution to produce the re-named and globally popular Bacardi Rum.

  • Lunch at La Aurora paladar
  • Visit Santa Ifigenia Cemetery, second only to Havana’s Necrópolis Cristóbal Colón in its importance and size
  • Visit Plaza de la Revolución “Antonio Maceo”
  • Nighttime suggestion: Enjoy Cuban jazz at Iris Jazz Club

DAY 4 Monday Santiago de Cuba-Miami

  • Get into the “Café Paths” and visit La Isabelica, a museum that treasures the history of Franco-Haitian emigration in Cuba

The steep road up the mountain range becomes increasingly beautiful as the foliage closes in and the valley opens up below.  Mango trees are ubiquitous. You will visit the ruins of many of the surrounding 60-plus coffee plantations on foot. Trails lead out from Cafetal la Isabelica.

Cafétal la Isabelica is a UNESCO Heritage Site. One of the first coffee plantations in southeast Cuba, this impressive two-story stone mansion, with its three large coffee drying platforms as built in the early 19th century by French émigrés from Haiti.

  • Visit the Don Pancho Taberna (old Bacardí Rum Factory) (time permitting)
  • Lunch at Brassa paladar
  • Head to Santiago de Cuba Antonio Maceo International Airport for your returning flight
  • Adios Cuba!

A Paladar is a privately owned restaurant, as opposed to regular restaurants that are owned and operated by the Cuban government. Palada-res 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 as many paladares as possible in our program to help local business and to provide you with the best Cuban restaurant experience.

What’s Included

Included items in the price of your tour:
  • Round trip airfare from Miami-Santiago-Miami
  • All meals listed on the itinerary
  • Pre-Departure document covers everything you need to know for a safe and enjoyable trip prior to arriving in Cuba. Upon arrival, a short orientation will acclimate you further.
  • All documents needed for legal travel authorization from the United States Treasury Department
  • All document processing including visas
  • Superior accommodations in Santiago
  • Expert tour leader
  • Air conditioned modern vehicle
  • All ground transportation for tours and airport transfers in Cuba
  • All activities and entrance fees to all activities listed on your legal itinerary
  • Concierge service for dinner reservations and shows/nightlife
  • Cuban Visa

Not Included:

  • Tips for tour leaders, local guides, wait staff, and chambermaids
  • 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  Melia Santiago
 TBD TBD  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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