Majestic 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.

Majestic Cuba Tour Dates 2022 & 2023

  • November 1 – 8, 2022
  • December 1 – 8, 2022
  • January 3 – 10, 2023
  • February 1-8, 2023
  • March 1 – 8, 2023
  • April 1 – 8, 2023

Day 1

  • Midday Arrival to Havana. (pending flight information).
  • 2:30 pm Meet your local guide at the exit of the terminal, change money, use bathroom and board bus to Pinar del Rio.
  • 5 pm Arrive in Viñales. Considered by many to be the most beautiful place in Cuba, the Viñales Valley National Monument holds stunning landscapes. The area is also famous for being the premier tobacco growing area in the world.
  • Check-in at bed and breakfasts, known as “casas particulars,” or “private homes.” Since the 1990s Cuban families have been permitted to rent rooms out of their family homes to foreigners. Featuring comfortable accommodations and ample privacy, it’s a great way to interact with everyday Cubans.

Evening Photo walk to catch the sunset.

  • 7 pm Welcome dinner with your host family at your local bed and breakfast.

Day 2

  • 6 am Meet at one of the casas for sunrise photo walk. We will meet two local residents of the community who will take us to the top of the hill, for a view of the sun rising over tobacco farms. Approximately 15-minute walk to location, 1 hour shoot, and 15 minute walk back to hotel.
  • 9:15 am Photos at the lookout at hotel Los Jasmines offering a panoramic view of the beautiful valley and the unique Mogotes that surround it.
  • 10 am Visit the home of Benito, a local tobacco farmer who will teach us about the cultivation and production process, followed by a rolling demo. He might even light up a cigar or two for the group.
  • 11:30 am Enjoy a farm-to-table experience on the grounds of a local farm, Finca Paraiso Agroecologica (the agro-ecological Paradise Farm), where we will learn about Cuban agriculture and tobacco production, while indulging in an organic meal.
  • 2 pm Spend the afternoon in Viñales, ultimately winding up at Los Jasmines hotel for a sunset photo shoot.
  • 5 pm Depart for Havana. Stop for sandwiches en route.
  • 8 pm Arrive in Havana. Check-in at boutique, privately owned hotels. Originally deemed “casas particulars”, 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.

Day 3

  • 6 am 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.
  • 7:30 am 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.
  • 10 am 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. Visit to local boxing gym, where we will shoot photographers in action.
  • 12:30 pm Lunch and Photo workshop, at Hotel Parque Central conference room. (Pizza and drinks for lunch)
  • 4 pm Visit to local boxing gym, where we will meet with adult boxers. The first hour should be warmup, sparing and time for some portraits, the second hour should be 5-minute bouts.
  • 6 pm Visit the studio of photographer Daylene Rodriguez Moreno, critically acclaimed street and portrait photographer and member of Cuba’s Union of Artists and Writers. Basarrate #157 e/San Rafael y San Jose
  • 8 pm Dinner at Al Carbon paladar. Created by the owners of the immensely popular Iván y Justo, this new restaurant strikes out in a different but equally successful direction, specializing in traditional Cuban dishes cooked over charcoal.
  • 9pm Enjoy live Cuban Music

Day 4

  • 7 am 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)
  • 10:30 am Visit to agricultural market, 19 y B, Vedado to take in the local market, where Cubans buy fruits and vegetables.
  • 12:45 pm Lunch 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.

Free time to explore and shoot.

  • Optional: Take pedestrian ferry across Havana Bay to the community of Regla, a working-class, Afro-Cuban community with a thriving local culture. Regla is especially known for its strong ties to Santería and other Afro-Cuban religions. Explore the town for photo opportunities and visit the shrine to the Virgin of Regla.
  • 4 pm Enjoy a performance by Habana Compás Dance, which encompasses the rich rhythm and flow of the island, performing traditional and modern dances born from their Spanish, Cuban and Afro-Cuban heritage.
  • 6:30 pm Drinks and sunset photo shoot, at the rooftop of La Guarida, famous not only for its delectable dining, but also as the location for the film “Strawberry and Chocolate.” It is housed on the third floor of a large, old town house carrying the charming ambience of the early 1900s (drinks not included).
  • Optional: Dinner reservations at La Guarida paladar (meal not included)

Day 5

  • 7:30 am Early check-out and depart for the Ciénaga de Zapata National Park, to the south of the Matanzas province, it is famous for the Zapata Swamp, home to hundreds of endemic species of animals and plants, and the Bay of Pigs, the place of the invasion in 1961.
  • 9:30 am Wildlife photo shooting in Zapata with a local specialist guide.
  • 12 pm Visit Caleta Buena, located at the entrance of Bay of Pigs, it is a translucent protected cove with superb rock landscapes and abundant undersea life. Shoals of surgeonfish and striped red mullets can be found along the spectacular rocky outcrops, scarcely troubled by the moray eels that have found a home there. This spot is one of the most accessible and popular snorkeling sites in Cuba. Enjoy a packed lunch followed by free time to explore and shoot.
  • 3 pm Continue on to Trinidad, a UNESCO World Heritage Site, known for its cobble-stoned streets, pastel colored homes and small-town feel. We will stop at the lookout point to capture the sunset along the southern coast of the island.
  • 5:30 pm Arrive to Trinidad. Check-in at Casas Particulares.
  • Evening Group dinner at Casa Lola. Enjoy a live Cuban musician perform around the campfire.

Day 6

  • 6 am City Sunrise photo shoot. Walk to the highest point of the city to shoot the sun rising over the bell towers and colonial homes of historic Trinidad.
  • 8:30 am Breakfast discussion with Nancy Benítez, a local architect, historian and restoration specialist. Ms. Benitez will provide an overview of the city’s history from an architectural, economic and infrastructural point of view.
  • 9:30 am Visit to the city historic houses with Nancy Benitez. Families will allow us throughout the homes, where we can snap photos of a number of antiques from the 1950s and well beyond.
  • 12:30 pm Lunch at Real Café, set in a beautiful house in the historic center of Trinidad. It offers Cuban, international food as well as a wide variety of fish and seafood dishes.
  • 4 pm Visit to the archeological site San Isidro de los Destiladeros, near the city of Trinidad, it was a typical sugar plantation, operated with slave labor in the late 18th and early 19th centuries. Remnants of this thriving and historically underappreciated industrial heritage survive: an impressive owner’s house, three-story tower, cistern, main sugar factory, ancillary buildings, and dikes. Almost all are in ruins or in imminent danger of collapse. We will discuss about sugar cane in Cuba and slavery.
  • Stop at the Lookout on the way back to Trinidad.
  • Continue to Playa Ancon to catch the sunset.
  • 7:15 pm Walk to La “Bremesa” for an intimate group dinner prepared by Chef Johan Machin at his home and paladar. Calle Alameda no. 84

Day 7

  • 8:30 am Check-out and return to Havana.
  • Along the way, visit Cienfuegos, one of the country’s oldest and most beautiful cities. Often referred to as the “Pearl of the South,” Cienfuegos is one of Cuba’s only cities to display French and Spanish architecture. Housed on one of the country’s largest bays, the city offers beautiful ocean front landscapes, and is deeply rich in culture.
  • 10 am Photo Walk of Cienfuegos with Omar Valenti who will show us the ins and outs of this beautiful port city.
  • 12 pm Lunch at El Lagarto. With views and breezes from the bay of Cienfuegos, the location of El Lagarto is unbeatable. We will be joined by Omar Valenti, a local photographer.
  • 1:30 pm Visit to Castillo de Jagua, a local fishing village located near the entrance to the Bay of Cienfuegos. Explore the area and interact with neighbors.
  • 2:15 pm Continue on to Havana.
  • 5:30 – 6 pm Arrival. Check-in at private bed and breakfast.
  • 7:45 pm Private tour of La Fabrica de Arte Cubano, the brainchild of Afro-Cuban fusion musician XAlfonso, 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.
  • 8:30 pm Dinner resesrvation 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).

Day 8

  • TBD Check-out and depart for airport in Havana. (pending flight information)
  • Along the way, visit to La Finca Vigía. Formerly the home of Ernest Hemingway, today it still houses his expansive collection of books. It was here where he wrote two of his most celebrated novels: For Whom the Bell Tolls and The Old Man and the Sea. The beautiful grounds and bizarre tales from Hemingway’s many years in Cuba are captivating.


What’s Included

  • 7 night’s accommodations in Cuba
  • 1 night in the Viñales Valley in casas particulars
  • 4 nights in Havana at the upscale, private bed & breakfasts
  • 2 nights in Trinidad at upscale, private bed and breakfasts
  • Daily breakfast, 6 lunches and 4 dinners
  • Professional, bilingual guide for listed activities
  • Local ground transportation for listed activities
  • Pre-trip departure information
  • Compliance with U.S. Treasury Department regulations
  • Speaker fees
  • Tips for local guide and driver
  • Admission to all museums and public buildings listed in itinerary
  • Coordination of all listed activities
  • 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: $4,625
  • Double $4,225 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.