Cuba – Take a journey back in time


Offered by: Rodolfo Gonzalez (Pulitzer Prize-winning photojournalist and Rhodes Scholar Cuba specialist)

$4,000 per person

up to 4 people

8 days

Travel Photography

Cuba is a country best described as being frozen in time, presenting moments and culture from the 50s at every turn. It has only recently begun to thaw under economic progress amidst the growing rush of once-forbidden tourists. Most visitors to Cuba have a cliched reference of classic cars, perfectly-rolled cigars, and white-sand beaches, but Cuba is more than that and there are stories to be seen and told. Yet, these stories are not easily seen or captured. There are practical, ideological, and cultural challenges (let alone language) that could make an authentic Cuba experience available only to a select few.

Rodolfo’s many visits to the island exploring the streets of Havana, Trinidad, and the everyday lives of Cubans offer artists, photographers, and travel enthusiasts a unique perspective and photojournalistic plus street-photography approach to capture often missed moments in this 8-day visually immersive and cultural journey.

Rudy has often asked the Cuban people what makes them so passionate and happy despite the daily hardships. The common response with a simple shrug, wink, and always a smile is, “Why be unhappy?” Despite Communist rule and 60-plus years of “el bloqueo,” Cubans continue to remain resilient and vibrant. A friend says to him, “There are no problems here, only possibilities.”

Cuba offers so many photo opportunities that it’s best not to rush around with a checklist. This journey offers you the opportunity to see, immerse, and take in the subtle moments from both the past and present. Explore the streets, local hangouts, markets, villages, and countryside and interact with the people in Havana and Trinidad as you shoot side-by-side with a Pulitzer Prize-winning photojournalist, benefiting from his unique insights, storytelling approach, and a keen visual eye.

The best Cuba experiences are often had instinctively and on the spur of the moment. We might chat up a local, enter a boxing ring, hang out at a bar into the night or step onto a fishing boat depending on the situation and opportunity. For this reason, a degree of flexibility and an open-ended schedule is recommended. Having said that, below is a summary of what we will directionally aim to do during our time:

Havana (Days 1-4)

  • Sunrise and sunset walks along the famous Havana seawall, El Malecón, creating images of the fishermen and people-watching as generations of Cubans gather and socialize along the ocean-front boulevard
  • Street photography in the lanes of Old Havana that has maintained remarkable architectural integrity despite a glaring contrast between the space occupied by locals and that frequented by visitors
  • Visit the working cemetery El Cementerio de Cristobal Colon, founded in 1876 and named after Christopher Columbus
  • Experience a glimpse of Cuba’s Afro-Cuban heritage with music, rumba, and religion dance performed in Old Havana’s Callejon de Hamel, in addition to its dazzling array of street art and sculptures
  • Day-trip to Valle deViñales (190 kms from Havana), well known for its famous agricultural valleys and world-class tobacco
  • The Havana experience would not be an experience without seeing vintage classic cars, the organic farmer’s market, a local boxing ring, and local art

Travel day from Havana to Trinidad with a stop in Cienfuegos (Day 5)

  • Stop for lunch (legendary food scene in Cuba) and a little rest, and 3 hours of exploring the central square and life around it.
  • Marvel at and capture the Parisian flair blended with feisty Carribean spirit of this UNESCO World Heritage town against the backdrop of its 19th-century Spanish architecture

Trinidad (Days 6-8)

  • Street photography and people watching around Plaza Mayor and other pockets of this UNESCO World Heritage colonial town
  • Day trip to the Valley of Sugar Mills (including plantation visit) and the Tower of Manaca Iznaga
  • Visit local artists in studios to document contemporary art techniques, meet the artists and shoot them at work
  • Visit a nearby fishing village (half day trip) and explore the rural countryside

Note: There are limited flights available (depending on your destination) that fly out of Trinidad. You are welcome to fly out of Trinidad, or you can be dropped off at Havana the following day (Day 9). This time there will be no extended stops along the way, the drive time is approx. 5 hours.

Additional information

Booking requirement
Cuba trips need logistics, advance preparation, and in some cases, administrative paperwork. For these reasons, bookings for this journey must be made at least 45 days prior to the availability date as listed. Cancellations made within 30 days of this journey’s start date will lead to full forfeiture of payment.

Meeting point
Pick and drop off will be provided from Havana airport

Recommended equipment
Shooting and light condition change dramatically so fast lenses f/2.8 or faster are ideal for all lighting scenarios (including low light and interiors). Depending on your personal style or choice prime or zoom lenses that offer coverage of 24mm – 200mm is a very good range. We will be shooting instinctively on the streets quite a bit, so a 28mm or 35mm prime is also recommended. A small travel tripod is also ideal for early morning and evening photography.

Activity level
Medium to High — While there are no strenuous hikes or climbs, we will spend a lot of time on the streets and walk several hours almost every day.

Important Notes

What’s included:
– Hotel and/or Casa accommodations (clean, very comfortable and safe) for all nights
– A local guide throughout the trip to handle all local logistics
– All local transportation within Cuba
– Breakfast and 2 bottles of water every day
– Local tips (several places and people will expect donations)
– Local cultural exchange fees through agency and administrative work (as needed, depending on your nationality)

What’s not included:
– Flights to and back from Havana
– Lunch, dinner and other snacks or beverages are not included. We may dine together or separately throughout the trip (there is complete flexibility) but these costs are not included
– Any personal health, travel or gear insurance (you are responsible to obtain these ahead of your trip)
– Any local shopping such as gifts and souvenirs