After breakfast, we take an early morning 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. You will experience a more relaxed and hidden slice of Havana. Regla is a photographic masterpiece. In the afternoon, we’ll visit a fishing village known for its catches of marlin and swordfish, a favorite of Hemingway’s.

Later in the evening, we will visit La Fabrica de Arte Cubana for live music, art, and photography following dinner. La Fabrica de Arte Cubana was founded by Afro-Cuban rock star X Alfonso, who has turned this into a meeting place for young and eclectic Cubans and foreigners. (B) (L) (D)

We begin our day at a famous Havana boxing gym and community center run by local Cubans. Here we’ll enjoy a private photo session with Cuban boxers. Our private session will allow us to capture both environmental portraits and live-action sparring bouts after we’ll drive to Vedado. After, we’ll visit a “lost in time” centuries-old Cuban Mansion for a photography session with ballerinas in this nearby suburb. Built at the turn of the century, this home is truly a masterpiece and has remained untouched since the revolution in 1959.

After lunch, we will visit an American Classic Car restoration garage that has put together a fleet of over 20 pristine “Clasicos” (as Cubans refer to them), to provide professional car service to their clientele. Learn firsthand how they restore these classic American beauties from the 1950s. This setting makes for some amazing photography. Interacting with Cuban businesses and helping them learn how to improve is always our goal under “support for the Cuban people”.

Afterward, we’ll spend the afternoon in these beautifully restored cars, driving along the Malecón (Havana’s seawall), visiting the mansions in the Miramar neighborhood, and experiencing the bustle of Neptuno and San Lazaro streets in the city center. (B) (L) (D)

After breakfast, we depart Havana for a day trip to Viñales Valley, a UNESCO World Heritage Site. People don’t come to Viñales for the music or the mojitos; they come to dip indulgently into the natural world, hiking, horse-riding, or photographing some of the most beautiful landscapes in Cuba. In the valley, you’ll experience craggy limestone monoliths, and cigar-chewing guajiro’s driving their oxen and plowing through the rust-colored tobacco fields.

Despite its longstanding love affair with tourism, this slow, relaxed, wonderfully traditional settlement is a place that refuses to put on a show. What you see here is what you get – an agricultural town where front doors are left wide open, and everyone knows everyone else. We’ll be talking with local farmers and learning about their lives. We’ll enjoy lunch at an organic farm with a stunning view of the valley. We’ll visit the family farm of a private tobacco grower known for their world-famous Cohiba cigars. We’ll enjoy a relaxing dinner in Old Havana upon our return to Havana. (B) (L) (D)

After breakfast, we’ll explore Old Havana, a UNESCO World Heritage Site. 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 and important monuments. Photograph 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 de San Cristóbal de La Habana.

We will walk Prado Boulevard to the Malecón (seawall) in the late afternoon. On the weekends, the Malecón comes alive with thousands of Cubans chilling and enjoying the evening. We’ll walk the seawall and capture portraits and street images. We’ll meet with the owner of Malecón 663 and discuss her successful business model. Then set up for a sunset shoot, depending on the weather conditions.

We’ll end our last day in Havana with a dinner at La Guarida Paladar, famous for its delectable dining and as the location for the film “Strawberry and Chocolate.” It is housed on the third floor of a large, old townhouse carrying the charming ambiance of the early 1900s. (B) (L) (D)

After breakfast, we depart Havana for Trinidad, where we’ll check in to a lovely bed & breakfast located in the heart of the old city of Trinidad. The wonderful village of Trinidad is a UNESCO World Heritage Site known for its cobblestoned streets, pastel-colored homes, and small-town feel. Built on the back of the 19th-century sugar and slave trade, Trinidad flourished. At its zenith, in 1827, one of the 56 sugar mills in the region harvested the biggest cane haul in the world — just under a million kilos of white pressed crystals. This enormous, conspicuous wealth shaped the town, and no expense was spared in fashioning the finest Spanish colonial mansions, plazas, and churches, which still stand testament to the vainglory of this profiteering era.

In the late afternoon, we will explore the city’s rural areas. Many areas are off the tourist grid and make for some beautiful photographic opportunities. If the sunset is looking right, we’ll shoot it from the top of the famous bell tower. We’ll enjoy a wonderful dinner at one of the many local paladars in the evening. (B) (L) (D)

We are up early for a sunrise photo walk through Trinidad. Here we will witness the city come to life (well before the tourists arrive). Not only is the light at its best, but the photographic opportunities are seemingly endless—afterward breakfast at our casa.

In the afternoon, we drive to the Valley de los Ingenios (Valley of the Sugar Mills), a UNESCO World Heritage Site, where you can get a sense of the sugar mill lifestyle of the 19th century. Located just outside of Trinidad are three interconnected rural valleys – San Luis, Santa Rosa, and Meyer – that make up the Valley de los Ingenios.

The former plantations, mill buildings, and other facilities and archaeological sites in the Valley de los Ingenios represent the richest and best-preserved testimony of the Caribbean sugar agro-industrial process of the 18th and 19th centuries and the slavery phenomenon associated with it. More than fifty sugar mills were in operation here at the industry’s peak in the 19th century, and in 1827 more than 11,000 slaves were working in the mills. A long, gradual decline in Cuba’s sugar industry accelerated significantly in the 1990s. We’ll set out for a twilight photo walk throughout downtown Trinidad in the late afternoon. After, we’ll enjoy dinner at one of the many local paladars. (B) (L) (D)

After an early morning walk in Trinidad, we depart for Cienfuegos. We’ll meet with a local photographer friend who will show us his unique technique for creating prints. He blends prints made in the darkroom with acids and other chemicals he can find throughout the home.

We’ll enjoy lunch on the Punta Gorda, and a photo walk before continuing on the Havana. We are back in Havana by late afternoon, where we will spend our last night together.

In the evening, we will enjoy our “Farewell Dinner” at one of our favorite private restaurants in Havana. (B) (L) (D)

Sunday morning, we meet for breakfast and our final discussion and photo review. After checkout, we will bid you farewell. The Cuban government and the airlines request that you check in at least 2.5 hours before your flight. (B)

Photo Workshop Adventures provides 100% legal and compliant travel for U.S. Citizens under the U.S. Treasury Department’s OFAC “Support for the Cuban People” category.

Throughout each day, we are committed to “Support for the Cuban People” under the General License 31 CFR § 515.574. Our goal is to promote independent activity intended to strengthen and support civil society in Cuba and constitute a full-time schedule that enhances contact with the Cuban people and results in meaningful interaction between ourselves and individuals in Cuba. We never pay for lodging at any property on the CPA List to the extent prohibited by § 515.210. In addition, we will support Cuban entrepreneurs launching their privately-owned businesses. Our only accommodations are private Cuban residences (casa particular). We only eat at privately-owned Cuban restaurants (paladares), and we only shop at privately owned stores run by self-employed Cubans.