Classic Cuba Tour Itinerary

Cuba is one of the most enchanting and captivating countries in the world, a pulsating and multifaceted blend of history, music, dance, gracious people and vibrant island culture. Join photographer Daryl Hawk on this unique opportunity to engage with the Cuban people and to discover the allure that is Cuba.

The people of Cuba are the country’s treasure and its most dynamic force. They are extremely friendly and generous of spirit, resourceful, resilient, and incredibly open to sharing their personal lives and their country with visitors. With our eyes and hearts open, we travel off the beaten tourist trail to better understand this intriguing country through direct exchanges with the Cuban people. Our upscale privately run hotel is owned by individuals who have a flair for design, amazing service and a unique charm.


Customized itineraries to match your specific interests available – discount available for private groups.

Day 1 – Havana

Check-in at one of our privately owned boutique hotels, La Posada de Chacon or Fresko Habana. Originally deemed “casas particulares”, the idea by the Cuban government was to allow small steps in the private sector. Over the past decade, there has been an influx of privately run hotels/bed and breakfasts, that not only helped solve the demand issue for tourism, yet offered charming experiences and equal to better caliber lodging options than traditional hotels on the island.


Orientation with local guide. Discuss the week ahead as well logistical issues such as changing money and other cultural norms.

Walk from hotel to the Malecon and watch the waves crash on the seawall. Continue to the rooftop of the Hotel Prado for a view of all of Havana followed by a drink at Ernest Heningway’s favorite bar, La Floridita listening to live Cuban music. The walk will continue down the Paseo del Prado, a tree lined street where people congregate and you see amazing architecture on both sides of the avenue. We finish our walk at Old Havana Plaza where you will be treated to a sumptuous dinner at La Vitrola while listening to live Cuban music.


 Day 2 – Havana – Plazas, Revolution Museum, Fabrica De Arte

  • Breakfast at home
  • 9:00am: Walking tour of the Old City. Wander through the Plaza de Armas, a scenic tree-lined plaza formerly at the center of influence in Cuba. It is surrounded by many of the most historic structures in Havana as well as important monuments. See the Plaza de San Francisco, a cobbled plaza surrounded by buildings dating from the 18th century, dominated by the baroque Iglesia and Convento de San Francisco dating from 1719. Visit the Plaza Vieja, surrounded by sumptuous houses of the Havana aristocracy from the 18th and 19th centuries. Visit Plaza de la Catedral and the Catedral de San Cristóbal de La Habana.
  • 1:00pm: Lunch at Mohito Mohito restaurant.
  • 2:00pm: After lunch we then continue to the National Hotel, a historic Spanish eclectic style hotel, opened in 1930.
  • 6:30pm: Take a stroll down the Malecon before an 8pm dinner at the legendary Buena Vista Social Club and enjoy a 3 course dinner and live performances of salsa, rumba, bolero, guaguanco and much more!

Day 3 – Day Trip to Soroa and Vinales

Breakfast at home. Day trip in a beautiful 1950’s Chevrolet to Soroa, “the rainbow of Cuba”, a gorgeous mountain community. Arrive in Soroa at 9:30 and experience the magnificent hillside gardens at Orquuideario Soroa, which has the largest collection of orchids in Cuba – over 700 species. We then take a short hike to the magnificent Salto de Arco Iris. Swim in the natural pools in the cool refreshing water with amazing photo opportunities. Considered to be one of the best waterfalls in Cuba.

Our journey continues to Vinales, considered by many to be the most beautiful place in Cuba. The Viñales Valley is a National Monument and a UNESCO World Heritage Site. It is encircled by mountains and its landscape is interspersed with spectacular dome-shaped limestone outcrops (mogotes). Traditional techniques are still in use for agricultural production, particularly tobacco, which makes Viñales famous for being the premier tobacco growing area in the world. Our excursion will include a visit a tobacco farm to learn about the cultivation and production process, a stroll through the valley with a local guide and time to explore the town center.  We will also visit an Indian cave and Mural Prehistorica.

Return to Havana and dinner at Cha Cha Cha, one of Havana’s most eclectic restaurants.

Day 4 – Ernest Hemingway’s House, Exploring Havana’s Coastline and Buena Vista Social Club

  • Breakfast at home
  • The day begins at 10am with a visit to Finca Vigia, the home of Ernest Hemingway, which was kept exactly the same as when when he lived there. See his famous fishing boat, Pilar!
  • Take a 1950s Chevrolet and view Havana’s coastline area and fishing community. We visit Cojimar where Ernest Hemmingway spent a lot of time fishing and hanging out.
  • 6:30pm: Take a leisurely drive in a 1950s Chevrolet, cruising the neighborhood of Vedado – some of the most amazing architecture in almost all of Cuba. Dinner at Tierra, Havana’s newest international dining spot. Located inside a container in the Fábrica de Arte Cubano, the restaurant mirrors the eclectic crowd, serving dishes from around the world. La Fabrica de Arte Cubano, the brainchild of Afro-Cuban fusion musician X-Alfonso, this is one Havana’s finest new art projects, an intellectual nexus for live music, art expos and fashion shows that has turned into a meeting spot for a young, eclectic crowd of Cubans and foreigners.

Day 5 – Havana – Fusterlandia, Rum Museum and Fort Ceremony

  • Breakfast at home
  • 9:00am: Visit Fusterlandia – a neighborhood that has been turned into a masterpiece of intricate tile work and kaleidoscopic colors by famous artist Jose Fuster.
  • We then continue to the Hemingway Marina. 
  • We return to Old Havana for a stroll around the Plazas before 1pm lunch at La Vitrola listening to live Cuban music.
  • We continue to the Museum of Ron Havana Club where you will learn about the history and the process of making Cuban rum, along with rum tastings.
  • We continue our stroll through Plaza Vieja to see a car museum and then walk up Obisbo street, the livliest street in Havana!
  • 6:00pm: Dinner at Antohos restaurant.
  • 8:00pm: We go to the cannon blasting ceremony at the famous Castillo Del Morro which is a tradition that dates back to the colonial era.

Day 6 – Departure

  • Say Farewell (for now). Depart for Jose Marti International. Recommended that you arrive to airport at least 2.5 hours prior to flight departure.


What’s Included

  • Private hotel as mentioned in the itinerary

  • Meals as per itinerary

  • All ground transportation in Cuba to organized activities

  • Admission to all scheduled educational  and special activities

  • English-speaking local guides

  • 24 hour english speaking concierges service at hotel

  • Daryl will be taking photos of all the participants throughout the trip and recieve them when you get 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


  • Single: $3,495
  • Double $2,975 each

A big part of the reason that I go to Cuba is for humanitarian reasons. Due to the poor economy the Cuban people are struggling and are in desperate need of basic goods. If you wish, you can bring toothbrushes, asprin, vitamins, pens, soap, etc. which will be greatly appreciated.


To register and for more information, contact us here.

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