“Chris was the perfect trip leader. His knowledge of the country and its history is vast and he enthusiastically wanted to share it with us along with his years of experience as a photographer… He’s talented, interesting, accessible, and fun to travel with. Plus, he really did seem to care about each of us — if we were okay, getting good images, too tired, too hot, etc. I would certainly travel with him again. He certainly kept up the high standards of a Jim Cline Photo Tour.” – Judy B., Colombia 2018

NOTE: On June 4, 2019, the Trump administration rescinded the “people to people” educational exchange license. However, our program is grandfathered in for clients who have already requested a reservation, and will continue to operate as a “people-to-people” program for 2020. For future trips, every U.S. citizen can still legally travel to Cuba and group travel is still possible, pre-approved, under the “support for the Cuban people” license. Jim Cline Photo Tours’ Cuba programs are designed to maximize “support for the Cuban people” through stays at private B&Bs, meals at private restaurants, and interactions with independent artists, private tobacco farmers, etc.


Experience Cuba with the locals in three of the island’s most iconic sites… Havana, Viñales and Trinidad.

Cuba’s frozen-in-time stage-set backdrop lends a twilight zone ambiance that Hollywood couldn’t dream up if it tried. It guarantees superb photography. But Cuba’s real magic isn’t its crumbling architecture, one-of-a-kind revolutionary icons, or spruced-up vintage cars. It’s the seemingly mundane, quintessential experience a lo cubano that provide for the most authentic grass-roots photography and which you’ll forever cherish as favorite take-aways.

No-one knows Cuba as well as renowned travel journalist, National Geographic photographer, and Cuba expert Christopher P. Baker. Chris has authored and illustrated six travel books on Cuba, and has written about and photographed Cuba on behalf of entities from the BBC and CNN to National Geographic, New York Magazine, and Playboy during three decades of travel to Cuba.

Join Christopher on this memorable one-of-a-kind photo tour, inspired by research for his magazine assignments and guidebooks. Of course, we’ll get to see many of the finest iconic sights that Cuba has to offer. But Chris shuns the usual tourist locations to explore off-the-beaten-path Cuba and interact with Cubans from all walks of life, while taking advantage of the best light, and with a flexibility that allows us to make the most of opportunities as they arise.

On this trip, we will experience the very best photo destinations that Cuba offers

We will start in Havana, with its world-class street shooting and so much more. We will organize photo shoots, such as the most important boxing gym in Cuba, Afro Cubano dancers in an old colonial building, and ballet dancers from the Cuban National Ballet posing in an old mansion. We will be assisted local Cuban photographers, and everywhere we go we will meet and photograph the friendly people of Havana.

Next we will explore the tobacco-growing region of Vinales – with its stunning limestone cliffs, or Mogotes. Vinales would be an important photo destination just for the scenery alone, but it is the traditional farmers that make it so great. We are friends with many of the farmers in the area, and they will invite us into their homes, affording photo opportunities that the typical group will never have. Also we’ll be working with a local photographer who was born and raised there.

Finally we will journey to the colonial city of Trinidad. Many consider this Unesco World Heritage site the most beautiful city in Cuba. With the backdrop of the perfectly preserved colonial buildings, we’ll photograph cowboys riding horses and pulling horse-carts through the cobblestone streets, along with the classic American cars. We’ll meet a local photographer there and visit a cowboy ranch outside of town, where we’ll be served an authentic country-style lunch. Trinidad also hosts a thriving local live music scene, and we will have the opportunity to photograph local musicians there.

This trip will comply with the U.S. People-to-People travel sanctions.

March 8-17, 2020 SOLD OUT!
November 30-December 9, 2020
February 28-March 9, 2021
$4,675 (March 2020)
$4,775 (November 2020)
TBD (2021)


Day 1: Sunday
Arrive on your flight to Havana, you’ll be picked up at the airport and transferred to our B&B in the heart of Old Havana. We’ll have a 5:30 p.m. orientation meeting, then ride along the Malecón in sexed-up Eisenhower-era convertibles for a welcome dinner at La Guarida—Cuba’s most famous (and photogenic) restaurant and the set for the Oscar-nominated movie “Strawberry & Chocolate.”
Overnight: Private B&B, Havana

Day 2: Monday 
Walking the earthy back streets of the colonial quarter with our local Cuban photographer-guide, Chris will regale you about the city’s fascinating history while meeting every-day Cubans along the way. Chris will take you inside humble homes to photograph speakeasy nail salons, santería shrines, etc. In the afternoon we’ll take an excursion to Plaza de la Revolucíon Square, the famous Hotel Nacional, and the El Morro fort, which guards the entrance to the harbor. We’ll finish the day with a walk to the famous Malecon, the walkway along the sea. We’ll photograph the sunset, with old cars rumbling by as they rumble along this seafront boulevard offering a microcosm of Cuban life: the elderly walking their dogs; fishers casting their lines, or casting off in great inner-tubes; musicians practicing their instruments; and, since this is Cuba, no end of lovers canoodling.
Overnight: Private B&B, Havana

Day 3: Tuesday 
We’ll have an optional early morning photo walk through Habana Vieja. Later, we’ll visit tumbledown Gimnasio Rafael Trejo, an unlikely venue where Cuba’s future boxing greats train. After lunch, we’ll photograph a dance performance. In the late afternoon, we’ll meet at the Malecón, the miles long sea-walk, for sunset and twilight before walking to dinner. We’ll witness the classic American cars .
Overnight: Private B&B, Havana

Day 4: Wednesday
In the morning, we’ll visit a “lost in time” 1913 mansion gone to ruin and whose occupant lives surrounded by all-things pre-revolutionary: everything in the house dates from the 1950s (or older). Here we’ll shoot one or more professional models for stunning travel portraiture in an astounding setting. We’ll then walk a few blocks to visit one of Chris’ closest friends to witness and photograph how he maintains his beat-up 1948 Buick and fleet of pre-revolutionary motorcycles. In the afternoon there will be free time for optional activities and dinner on your own. This evening we will have an optional excursion to the famous Tropicana floor show.
Overnight: Private B&B, Havana

Day 5: Thursday
In the morning we’ll drive from Havana to Viñales, arriving for lunch at a private restaurant with an amazing view over the Vinales Valley with its dramatic limestone formations called mogotes. We’ll stop at a tobacco farm, and get a cigar rolling demonstration, check in to our B&Bs and have the late afternoon to meet the locals in the town, through sunset time.
Overnight: B&Bs, Viñales.

Day 6: Friday
We’ll get up early and visit tobacco farmers and photograph them in the morning light. We’ll have lunch at a beautiful restaurant where all of their organic vegetables are grown in their adjacent farm. In the afternoon we’ll visit more farmers and photograph them in and around their homes and barns. They will invite us into their homes, where we will learn about their daily lives. We’ll have dinner at a tobacco farmer family “restaurant”.
Overnight: B&Bs, Viñales.

Day 7: Saturday
We’ll drive from Viñales to Trinidad, with a lunch stop on the way. Passing through Cienfuegos in mid-afternoon, we’ll stop briefly to photograph a former sugarcane community, including inside a ration store adorned with astonishing revolutionary murals. We’ll then drive along the Caribbean shoreline, arriving the colonial town of Trinidad in time for the last light. We’ll reward ourselves after a long-drive today with dinner in one of Trinidad’s most sensational private restaurants (paladares).
Overnight: Hotel E La Calesa, Trinidad.

Day 8: Sunday
We’ll rise early for a golden hour walk, letting serendipity guide us through the streets of Trinidad, immersing ourselves in the local life as we shun the touristy quarter in favor or lesser visited quarters. Chris will introduce us to an artist friend whose ingenious one-of-a-kind wood-crafts are to be seen to be believed—a sublime photogenic experience. We’ll spend the rest of the day in and around this magnificent UNESCO World Heritage Site, meeting the local people and learning about their lives. We will get a look inside the homes of many Cubans. Free time to wander the streets and photograph in the afternoon. After each person has dinner, we’ll head to the colonial home of Trinidad photographer Julio Muñoz for image sharing.
Overnight: Hotel E La Calesa, Trinidad.

Day 9: Monday
We’ll have the whole day to photograph in the colonial gem of Trinidad, some time with the group, and some of the time on your own. Cubans love to head to the beach on weekends. We may join the Muñoz family for lunch and the afternoon at La Boca, where we’ll feast beside the sands among other Cuban families. Or maybe we’ll all head out to a farm ranch for lunch and an afternoon with the cowboys. This evening you may visit one or more of the thriving live music venues in the center including the famous Casa de la Trova.
Overnight: Hotel E La Calesa, Trinidad.

Day 10: Tuesday
This morning journey over the Sierra Escambray mountains to Santa Clara, the city famously associated with Che Guevara. We’ll make a de rigeur stop to visit  the monument, memorial, and mausoleum of Che on Plaza de la Revolución before lunch at a local paladar. In the afternoon, we depart Santa Clara for Miami and home.