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.

Classic Cuba Tour Dates 2022 & 2023

  • November 9 – 16, 2022
  • December 9 – 16, 2022
  • January 11 – 18, 2023
  • February 9 – 16, 2023
  • March 9 – 16, 2023
  • April 9 – 16, 2023

Day 1 – Thursday (to Havana)

  • Arrive in Havana. Allow up to two hours at the Havana airport for customs, immigration, etc.
  • Walk and photograph with Daryl and your Cuban Photographer from Malecón to Paseo del Prado.
  • 1:00pm: Lunch at a local paladar
  • 3:00pm: Check into your private “casa”
  • 5:00pm: Shoot the sunset along the Malecón in El Vedado, near our homestay
  • 6:30pm: Drinks at the Hotel Nacional ($).
  • 8:00pm: Bus from the Nacional hotel to dinner at paladar La Mansion Castillo
  • Return to casa

Day 2 – Friday (Havana)

  • Breakfast at home
  • 8:30am: Tour Havana in restored classic American cars. Opportunities to photograph at point of interests with the old cars.
  • 11:00am: Visit “Artefacto” for a Cuban Photographic Exhibition
  • Walk through La Habana Vieja (Old Havana) with our Cuban photographer/guides
  • 1:00pm: Lunch at a local paladar in the Old Town
  • 2:30pm: Visit Taller Experimental de Gráfica de La Habana — printing and engraving.
  • 3:30pm: Bus to the a Dance Company for a rehearsal photo session
  • 5:30pm: Bus back to casa
  • 7:30pm: Bus to dinner at a nearby restaurant
  • Return to casa

Day 3 – Saturday (Havana)

  • Breakfast at casa
  • 8:00am: Bus to early walk in La Habana Vieja with our Cuban photographer/guides.
  • Walk and photograph in La Habana Vieja and Centro Habana.
  • 1:00pm: Lunch at Cafe de Los Artistas
  • 2:30pm: Walk and shoot in La Habana Vieja or early bus back to the hotel for siesta.
  • 5:00pm: Bus from hotel (or walk) to Castillo de San Salvador de La Punta for sunset shot with ballerinas
  • 6:45pm: Walk from La Punta to dinner at paladar Michifu
  • 10:00pm (optional): Show at Cabaret Parisien at Hotel Nacional (cabaret $25 cover). ($)

Day 4 – Sunday (to Viñales)

  • Breakfast at casa
  • 9:00am: Depart via bus to Viñales.
  • 1:00pm: Lunch at Balcon del Valle  
  • 3:00pm: Check in at the casas particulares (private homes) where we will be spending two nights
  • 4:00: Visit a tobacco plantation with a tour guided by a biologist.
  • 7:30pm: Dinner at home with families
  • Overnight at casas particulares, Viñales.

Day 5 – Monday (Viñales)

  • Breakfast in your casa particular.
  • Walk and shoot in Viñales.
  • 10:00am: Bus to Cueva del Indio
  • 11:00am: Visit the archeological museum and a farmer’s home to get to know the life in the countryside of Cuba.
  • 12:00pm: Stop for a Pina Colada ($) at the “prehistoric” mural
  • 1:00pm: Lunch at Finca Paradiso (Be prepared for a huge meal!)
  • 2:30pm: Bus back to Havana
  • Check in at private casas
  • Dinner at Paladar Cha Cha Cha
  • Attend the Cañonazo Colonial Ceremony
  • Overnight at casas particulares.

Day 6 – Tuesday (Havana)

  • Breakfast in your casa particular.
  • Bus to Trinidad
  • Lunch at a local paladar in Playa Larga  
  • Visit the Museum at Playa Giron
  • Check into our casas particulares in Trinidad
  • 7:00pm: Dinner at Vivian y Pablo’s 
  • 9:00pm (optional): Live music at Casa de la Trova ($)
  • Overnight in casas particulares, Trinidad.

Day 7 – Wednesday (Trinidad)

  • Shoot on your own after sunrise.
  • Breakfast in your casa particular.
  • 10:00am: Tour the town including a lecture by the historian of the village and a visit to the art gallery of Danilo Moreno and Yudith Vidal.
  • Lunch at Taberna La Botija 
  • Siesta or shoot in Trinidad.
  • 4:00pm (optional): Bus  to the beach, Playa Ancon! Learn about the barrier reef and environmental protection in the area. Return by bus at 6pm. Alternatively, walk and shoot in Trinidad.
  • 7:30pm: Farewell dinner at paladar Museo 1514
  • Optional: Enjoy the music and dance at Casa de la Musica ($)
  • Overnight in casas particulares, Trinidad.

Day 8 – Thursday (to Havana)

  • Breakfast in your casa particular.
  • 8:30am: Bus from Trinidad to Havana.
  • 1:00pm: Lunch at paladar El Divino.
  • Bus to the airport.

Fly to Miami, arriving by night.


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: $5,225
  • Double $4,325 each

NOTE REGARDING Majestic Cuba Tour:

Please note that this itinerary is subject to change. Due to the unique nature of our programming, each departure is custom designed and not every activity listed on this itinerary is always available. Please rest assured that our team in both Cuba and the U.S. take extra care in planning each excursion and draws from almost two decades of experience, relationships, and activities to make each itinerary exceptional.


To register and for more information, contact us here.

Meet Your Guide, Daryl Hawk!

Majestic Cuba Tour

Classic Cuba Tour

Books by Daryl Hawk