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 through your lens.

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 hotels are owned by individuals who have a flair for design, amazing service and a unique charm.

Day 1 – To Havana, Stop for sandwiches en route.

Check-in at boutique, privately owned hotels. 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.

Happy hour cocktails and discussion with Giulio Ricci, Cuban economist, about the current process of economic reform. He will share his views on the Cuban government’s “updating” of the economic model.

Sunset ride in Classic Cuban convertibles. Explore the Western side of Havana. Cruise the streets of Vedado and into Miramar and Playa. The history of western Havana is rich, as 5ta Avenida is lined with colonial mansions, embassies, and was home to the affluent community of Havana.

Welcome dinner at Vistamar paladar in Miramar neighborhood. This private restaurant is on the 2nd floor of an attractive residence that looks out to sea.

Day 2 – Havana

  • Breakfast at home
  • 6:00am: Sunrise photo shoot at Morro Castle. Today we will take the bus to Morro Castle, where we can get a view of the sun rising above the Alamar Housing projects and Eastern Beaches.
  • 7:30am: Photo walk along Prado Avenue and Havana’s seawall (Malecon). Catch Cubans on their way to work and school, and all the hustle and bustle of the city, followed by breakfast at your hotel.
  • 9:30am Socio-economic discussion with urban planner Miguel Coyula, whose presentation will. touch on housing, infrastructure, investment and restoration programs. It’s bound to leave you with a better understanding of why Havana looks the way it does today and possibilities moving forward.
  • 11:30pm: 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.
  • 1:30pm: Lunch at a Havana paladar
  • 3:30pm: Visit to the Lizt Alfonso Academy, a women-led dance company and school for local youth, specializing in various types of dance. We will watch a private performance by the adolescent dance group and sit with the dancers afterward to discuss how they came to join the school and the impact it has had on them. The talent and work ethic at this school is impressive.
  • 6:30pm: Cigar tasting with a local expert at Café Madrigal. He will explain the qualities and traits of fine Cuban cigars and how to properly light and smoke what is considered the finest tobacco in the world. Café Madrigal, owned and run by film director Rafael Rosales, is housed in a beautiful colonial mansion with the walls lined with captivating artwork.
  • 8:00pm: Dinner reservation at Grados, a private restaurant defender of the traditional Cuban cuisine and member of the slow food movement. Each dish has a history which is thoughtfully laid out by chef Raulito Bazuk.

Day 3 – Day Trip to Soroa

Day trip 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. Enjoy Cuban food and lunch at Restaurant el Salto. The afternoon is spent taking 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. 4PM departure and return to Havana at 5:30. 7:00 PM Dinner and show with a wide range of Cuban musicians at the legendary Buena Vista Social Club.

Day 4 – Havana

  • Breakfast at casa
  • 7:00am: Sunrise photo shoot with models and Old American Cars. Our professional models will pose with this wonderful backdrop. (location: little plaza in front of church next to boxing venue)
  • 10:30am: Cuba’s Growing Private Sector. Visits to private businesses in various sectors of the Cuban economy, and discussion about their start-ups, challenges and opportunities.
  • 12:45pm: Lunch at Havana paladar
  • 2:30: Visit to the studio of Wajiros Films, a collective that specializes in the production and development of audiovisual content to create a more complete and modern vision of Cuba, making artists and stories visible without the cultural and geographical stereotypes of the country.
  • 4:00pm: Discussion about Cuban culture and art with a family of artists at AltaMira. A few years ago, Edel Bordón and his family embarked on a journey to establish an art collective in their apartment building. Spearheaded by his wife Yamilé Pardo, the family created the AltaMira art space, which features an exhibition and workspace off of the main lobby and collaborations with neighbors.
  • 5:30pm Optional photo workshop with Daryl Hawk at hotel Dinner reservation at Cinco Sentidos. A few stone’s throw from the Kempinski Hotel and Museo de Bellas Arte, Cinco Sentidos raises the culinary bar in Havana. Cinco Sentidos’ masterful chef receives invitations by international luminaries to cook in their kitchens in Spain, in Morocco—but he always returns to his passion project in Havana

Day 5 – Day Trip to Viñales)

  • Day Trip to Viñales (approximately 2 1/2 hours from Havana), 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, lunch at a farm, a stroll through the valley with a local guide and time to explore the town center.
    Return to Havana
  • 8:00pm: Dinner reservation 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 (meal not included). 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 6 – Wednesday (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 Casas as mentioned in the itinerary

  • Meals as per itinerary

  • All in ground transportation in Cuba to organized activities

  • Admission to all scheduled educational activities and exchange program

  • Letter of Certification and  Regulations from US Department of Treasury

  • English-speaking local guide and local photographer

  • 24 hours emergency phone number while in Cuba

  • Daryl will be taking photos of all the participants throughout the trip. Everyone will receive a hardcover memory book documenting their trip. 

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.)


  • Single: $3,325
  • Double $2,925 each


To register and for more information, contact us here.

Meet Your Guide, Daryl Hawk!

Classic Cuba Tour

Books by Daryl Hawk