The Majestic Cuba Tour Itinerary

Santiago de Cuba

Santiago de Cuba is known as the “cradle of the Revolution” and is home to much Cuba’s famed music, like the Son. There are also museums, colonial churches and buildings of more recent historical importance, such as the Moncada Barracks, which are well worth exploring!

Santiago de Cuba has a very vibrant traditional music scene, which wil entice even teh shyest dancer out to experiment with some salsa moves. Culturally, Santiago has a different feel to the rest of Cuba, undoubtedly coming from the mix of Frech speaking slaves from Haiti and its proximity to Jamaica.


A spectacular drive past the region’s most controversial leasehold of Guantanamo Bay, then along the coast and finally through lush mountains of eastern Cuban, brings us to Cuba’s first colonial capital. When Christopher Columbus first encountered Cuba it was here and he duly noted in his log-book that this was the most beautiful land that human eyes could set upon. You will understand what he meant when you see the beaches and verdant mountain landscape that surround Baracoa. Situated on a beautiful bay wiht the mountains of the Sierra del Purial in the background, Baracoa was the first settlement founded by the Spanish in Cuba and was only accessible by sea until the end of the 1960s. There are numerous options for outdoor activities in the nearby mountains, rivers, waterfalls and beaches.

Customized itineraries to match your specific interests available.

Day 1 – Fly to Santiago de Cuba – 3 nights in Santiago de Cuba

Day 2

  • Walking tour of Santiago de Cuba in the morning
  • Drive to El Cobre, Cuba’s most important church (in the early afternoon)
  • Drinks and dinner at the Grand Hotel rooftop, overlooking the entire city and bay
  • Special fort ceremony at night

Day 3

  • Road trip to Grand Piedra, Cuba’s highest mountain area to experience the magical gardens and coffee plantation
  • Stops along the way for photo opportunities
  • Music at the Casa de La Trova in the evening

Day 4 – 2 nights in Baracoa

  • Drive to Baracoa on the famous La Ferola roadway in the morning
  • Walking tour of the Baracoa area in the afternoon
  • Dinner at the Marco Polo restaurant and music at La Trova

Day 5 

  • Walk the entire Malecon at sunrise for amazing photos of the town with the perfect light on the colorful buildings, coastline, bay with a historic ship, etc.
  • Excursion to Humbolt National Park in the morning
  • Maguana beach in the afternoon
  • Dinner and music at La Trova

Day 6 – Final night in Santiago de Cuba

  • Walk to historic cave area
  • Drive to Santiago de Cuba
  • Dinner followed by music at Casa de La Tradiciones

Day 7 – Fly Home


What’s Included

  • Private casa or boutique hotel as mentioned in the itinerary

  • Meals as per itinerary

  • All ground transportation in Cuba to organized activities

  • Admission to all special activities

  • English-speaking local guides

  • Daryl will be taking photos of all the participants throughout the trip. Everyone will receive the photographs when they return home. 

Not Included

  • Round-trip airfare
  • Meals and activities other than listed on itinerary
  • Individual house or hotel expenses (mini bar, room service, laundry fees, etc.)
  • Alcoholic beverages
  • Tips for taxis, guides, etc.


  • Single: $3,900
  • Double $3,300