📸 Photographing Magical Cuba!
Photographing Cuba - Enhance your Senses
An Immersive Cultural and Visual Experience
This unique photographic adventure is designed to help you capture the soul of Cuba through your lens, with expert guides at every step. From the timeworn streets of Habana Vieja (Old Havana) to the breathtaking limestone mogotes of Viñales Valley, you’ll explore some of Cuba’s most iconic and visually arresting locations.
Our journey begins in Habana Vieja (Old Havana), a street photography paradise. You’ll enjoy behind-the-scenes photo sessions in remarkable locations curated by National Geographic Photographer, Christopher Baker (when available), such as a gritty, colorful boxing gym, an Afro-Cuban dance troupe performing in a crumbling colonial theater, and ballerinas from the Cuban National Ballet posing in an exquisite, timeworn mansion.
All Photos by Christopher Baker
In Viñales, Cuba’s fabled tobacco-growing region, you’ll photograph landscapes of astonishing natural beauty—but it’s the people who make it unforgettable. We’ll be welcomed into the homes of traditional tobacco farmers, offering rare and intimate access far beyond the typical tour experience. We’ll also be joined by a local Viñales-born photographers, who brings rich cultural context to every moment.
Trinidad: Colonial Elegance & Authentic Cuba
We conclude in Trinidad, a UNESCO World Heritage Site often described as Cuba’s most beautiful city. With its colorful facades, perfectly preserved 18th-century architecture, and cobblestone streets, it’s a dream for photographers. We’ll photograph cowboys on horseback, explore a working cattle ranch in the countryside, and enjoy a traditional country-style lunch.
Trinidad pulses with energy and music. You’ll have opportunities to capture local musicians in evocative settings and soak in the city’s vibrant street life. As a special treat, Christopher has arranged several exclusive surprise shoots, including—when available—a quinceañera session in a dramatic colonial setting, offering a once-in-a-lifetime chance to document one of Cuba’s most treasured cultural traditions.
DATES: Custom dates available for singles, couples, or small groups. Call for details.
COST: Starting at only $3995
$400 single supplement
DAILY ITINERARY (subject to change)
Day 1: Arrival in Havana & Welcome Dinner
Arrive in Havana, where you’ll be met at the airport and transferred to our charming private B&B in the heart of Old Havana. Settle in and soak up the ambiance of this vibrant, historic neighborhood.
Overnight: Private B&B, Old Havana
Beautiful models on the stairs to La Guarida by Christopher Baker
Day 2: Exploring Old Havana & Sunset on the Malecón
Today we hit the streets with our local Cuban photographer-guide to explore the plazas and back alleys of Old Havana. They'll share insights into the city’s complex and colorful history while introducing you to local residents. These spontaneous encounters may lead us into humble homes, secret nail salons, Santería shrines, and more—offering rich opportunities for candid, powerful photography.
Later, head to Parque Central for a shoot featuring Havana’s iconic classic American cars, then stroll down the Prado promenade, through gritty, lively Centro Habana, and on to the Malecón. After sunset, we’ll walk a short distance to a local restaurant for dinner.
Overnight: Private B&B, Old Havana
Photos by Christopher Baker
Day 3: Boxing, Photography Legends & Afro-Cuban Dance
We’ll begin the day with an early morning photo walk and bicitaxi ride through the less-traveled southern side of Habana Vieja, en route to a gritty, timeworn gym where Cuba’s next boxing champions train. The light, the action, and the raw emotion here make for an unforgettable shoot.
After lunch, time permitting, we’ll visit the Galería Raúl Corrales, dedicated to the life and work of one of Cuba’s most iconic photographers. The gallery is run by his granddaughter, Claudia Corral, a talented contemporary photographer in her own right. The rest of the day is free for you to explore or photograph Havana at your own pace.
Overnight: Private B&B, Havana
Day 4: Ballet, Leisure & Optional Tropicana Show
This morning, we’ll photograph ballerinas from Cuba’s National Ballet in stunning, cinematic locations—including an exquisite, crumbling colonial mansion that feels suspended in time. These carefully arranged shoots offer some of the most elegant and evocative portraits you’ll create in Cuba.
The afternoon is at leisure for your own creative pursuits—visit a museum, schedule a café photo session, or simply take a break. Dinner is on your own tonight, and for those who wish, we’ll offer an optional evening excursion to the world-famous Tropicana cabaret, a dazzling spectacle of Cuban music, dance, and colorful costuming.
Overnight: Private B&B, Havana
Day 5: Havana to Viñales: Tobacco Fields & Sunset Views
This morning we’ll say goodbye to Havana and drive west to Viñales, Cuba’s beloved countryside escape. We’ll stop for sweeping views of the Viñales Valley, famed for its surreal mogotes—steep, lush limestone formations rising dramatically from the farmland.
Visit a tobacco farm, where we may enjoy a cigar-rolling demonstration and photograph traditional agricultural life. Later, position yourself for the golden-hour magic.
Overnight: Private B&Bs, Viñales
Day 6: Sunrise with Farmers & Rustic Viñales Life
We’ll rise before dawn for a sunrise shoot with local tobacco farmers, capturing the soft morning light as it spills across the fields and drying barns and meet a true local legend and a joy to photograph.
The rest of the day is free for you to relax or explore the quiet rhythm of rural life.
Overnight: Private B&Bs, Viñales
Day 7:Journey to Trinidad via the Cuban Heartland
Travel from Viñales to Trinidad, stopping along the way to photograph and explore Cuba’s diverse cultural and agricultural landscapes. Photograph a ration store adorned with striking revolutionary murals—a rare and gritty glimpse into Cuban life.
Pass through Cienfuegos, a coastal city with French-inspired architecture, and then drive along the Caribbean shoreline, arriving in the colonial jewel of Trinidad just in time for the golden hour. Later, celebrate with a dinner at one of Trinidad’s most sensational paladares—a beautifully restored private restaurant full of ambiance and flavor.
Overnight: Private B&Bs, Trinidad
Day 8 – Streets of Trinidad & Cowboy Country
Today, begin with an early morning golden hour walk, letting serendipity guide us through Trinidad’s lesser-known neighborhoods. Away from the tourist trail, we’ll capture the quiet poetry of daily life in one of Cuba’s most photogenic cities and UNESCO World Heritage Sites.
The afternoon is free to wander, relax, or explore the town at your own pace. This evening, you’re invited to enjoy Trinidad’s lively music scene, with an optional visit to Casa de la Trova, where local musicians light up the night in one of Cuba’s most iconic venues.
Overnight: Private B&Bs, Trinidad
Day 9 – Valle de los Ingenios & Farewell Celebration
This morning we venture into the Valle de los Ingenios (Valley of the Sugar Mills), a UNESCO World Heritage Site just outside Trinidad. Spend time in a nearby working farming community, offering more authentic portraits and lifestyle photography opportunities. Afterward, we’ll enjoy a rustic lunch at a traditional ranch, surrounded by the rural beauty of central Cuba.
The afternoon is yours to revisit favorite corners of Trinidad, dive into local galleries, or simply relax. In the evening, we’ll gather for an informal image-sharing slideshow, celebrating the creative spirit of the group. Then we’ll toast to our unforgettable journey with a farewell dinner at one of Trinidad’s most beloved paladares.
Overnight: Private B&Bs, Trinidad
Day 10 – Tour Santa Clara & Departure
This morning we’ll drive to Santa Clara, arriving in time for your midday flight to Miami and your journey home—carrying unforgettable memories and a collection of powerful, evocative images from your time in Cuba.
INCLUDED IN THE TOUR COST:
• Airport transfers: From José Martí Int'l Airport and return.
• Cuba Tourist Visa
• All breakfasts and welcome dinner. Other lunches and dinners as listed in tour itinerary.
• All activities, expert local guides, services, speakers, meetings and meals as described in tour itinerary except those noted as "optional" or "not included in cost."
• Air-conditioned transportation and a full-time driver where needed.
• Mandatory Cuban medical insurance coverage during your island stay.
• Expert photography instruction from a true Cuba expert!


















































