Cuba photo tour: Havana, Viñales & Trinidad

On this hugely popular itinerary, you'll get to photograph many of the finest iconic sights that Cuba has to offer, from the timeworn streets of Habana Vieja (Old Havana) to the fantastic limestone formations of the Valle de Viñales. But Chris shuns the usual tourist locations to explore some of his favorite off-the-beaten-path venues and with a flexibility that allows us to make the most of opportunities as they arise.

We'll start in Havana, with its world-class street photography. We'll also organize photo shoots, such as a funky and photogenic boxing gym, Afro Cubano dancers in a tumbledown colonial theater, and ballet dancers from the Cuban National Ballet posing in a sensational old mansion.

In the tobacco-growing region of Vinales, the scenery is nowhere surpassed in Cuba, but it is the traditional farmers that make it especially 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, a UNESCO World Heritage Site that is without a doublt the most beautiful city in Cuba. With the backdrop of the perfectly preserved 18th-century buildings, we’ll photograph cowboys riding horses and pulling horse-carts through the cobblestone streets. 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. Meanwhile, Chris has arranged a couple of fantastic surprise shoots, including of a quinceañera in a fantastic colonial setting.

ITINERARY (subject to change) / 11 days (2023 & 2024)
See below for 10-day 2025 itinerary (begins with November 2024 departure)

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 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 main plazas and back streets of the colonial quarter with our local Cuban photographer-guide, Chris will regale you about the city’s fascinating history while introducing you to Cubans along the way--a chance, perhaps, to poke and photograph inside humble homes, speakeasy nail salons, santería shrines, etc. We’ll finish the day with a late afternoon shoot of classic American cars around Parque Central, then walk along the Prado and through Centro Habana to the Malecón. We’ll photograph the sunset, with old cars rumbling by 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. From here we’ll walk the short distance to dinner.
Overnight: Private B&B, Havana

Day 3: Tuesday
We’ll have an early morning photo walk and bicitaxi ride through southern Habana Vieja en route to a tumbledown and uber-photogenic gymnasium where Cuba’s future boxing greats train. Time permitting, after lunch we’ll visit Galería Raúl Corrales, a studio dedicated to the famous photographer’s work and run by his granddaughter and contemporary photographer, Claudia Corral. We’ll then enjoy a private photo shoot with an exciting Afro-Cuban dance company. The rest of the afternoon is free for you to photograph Havana at leisure.
Overnight: Private B&B, Havana

Day 4: Wednesday
In the morning we’ll drive from Havana to Viñales, arriving for lunch at a private restaurant with an amazing view over the Viñales Valley, with its dramatic limestone formations called mogotes. We’ll stop at a tobacco farm, where we may get a cigar rolling demonstration, then check in to our B&Bs and relax before a late afternoon stroll in this quintessentially Cuban small rural town. Our sunset shoot will be at a hilltop organic farm-restaurant.
Overnight: Private B&Bs, Viñales.

Day 5: Thursday
We’ll get up for sunrise and visit tobacco farmers to photograph them in the early morning light. We'll breakfast at one such farm before heading to another tobacco farm, whose owner is one of Cuba's most colorful and photogenic personajes (personalities), The early afternoon is free before we visit more farmers and local residents, and photograph and interact with them in and around their homes and barns. We’ll have a roast suckling pig dinner at a family “restaurant”.
Overnight: Private B&Bs, Viñales.

Day 6: Friday
 we’ll drive from Viñales to Trinidad, with a stop en route at the Las Terrazas ecological mountain community. Passing through Cienfuegos in early-afternoon, 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: Private B&Bs, Trinidad.

Day 7: Saturday
We’ll rise early for a golden hour walk, letting serendipity guide us through the streets of this magnificent UNESCO World Heritage Site, immersing ourselves in the local life as we shun the touristy quarter in favor or lesser visited quarters. We hope to be accompanied by Chris’ long-time friend, local resident, and internationally-known photographer, The afternoon is free for you to explore Trinidad at leisure before we reconvene for a special themed shoot with a cowboy at a fantastic river venue, plus a visit to a nearby rustic former hacienda. 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: Private B&Bs, Trinidad.

Day 8: Sunday
This morning we’ll journey into the Valle de los Ingenios (Valley of the Sugar Mills), a UNESCO World Heritage Site where we’ll photograph a model in period costume at Chris’ favorite 18th-century hacienda, plus enjoy street photography in the nearby countryside hamlet. After lunch by the shore, the balance of the afternoon is free for you to explore and photograph Trinidad at leisure.
Overnight: Private B&Bs, Trinidad.

Day 9: Monday
This morning head back to Havana, stopping in Cienfuegos for brief exploration of the town’s colonial center and for a bayside lunch. We’ll precede lunch by photographing a former sugarcane community, including inside a ration store adorned with astonishing revolutionary murals. We’ll then continue to Havana, where the balance of the day is at leisure. Dinner is on your own.
Overnight: Private B&B, Havana

Day 10: Tuesday
In the morning, we’ll shoot two ballerinas of Cuba’s Ballet National  for stunning travel portraiture in one or two astounding settings, including a “lost in time” mansion. Your afternoon is at leisure for last minute purchases of cigars, coffee, and/or souvenirs… or perhaps an optional museum visit. This evening we’ll have an image sharing slide show before our farewell dinner at one of our favorite restaurants.
Overnight: Private B&B, Havana

Day 11: Wednesday
Today depart for Miami and home

ITINERARY (subject to change) / 10 days (2025)

Day 1: Sunday (November 16-25, 2024 begins on Saturday)
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 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 main plazas and back streets of the colonial quarter with our local Cuban photographer-guide, Chris will regale you about the city’s fascinating history while introducing you to Cubans along the way--a chance, perhaps, to poke and photograph inside humble homes, speakeasy nail salons, santería shrines, etc. We’ll finish the day with a late afternoon shoot of classic American cars around Parque Central, then walk along the Prado and through Centro Habana to the Malecón. We’ll photograph the sunset, with old cars rumbling by 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. From here we’ll walk the short distance to dinner.
Overnight: Private B&B, Havana

Day 3: Tuesday 
We’ll have an early morning photo walk and bicitaxi ride through southern Habana Vieja en route to a tumbledown and uber-photogenic gymnasium where Cuba’s future boxing greats train. Time permitting, after lunch we’ll visit Galería Raúl Corrales, a studio dedicated to the famous photographer’s work and run by his granddaughter and contemporary photographer, Claudia Corral. We’ll then enjoy a private photo shoot with an exciting Afro-Cuban dance company. The rest of the afternoon is free for you to photograph Havana at leisure.
Overnight: Private B&B, Havana

Day 4: Wednesday
In the morning, we’ll shoot two ballerinas of Cuba’s Ballet National  for stunning travel portraiture in two astounding settings, including a “lost in time” mansion. Your afternoon is at leisure for optional activities, and dinner on your own. This evening you can enjoy 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 Viñales Valley, with its dramatic limestone formations called mogotes. We’ll stop at a tobacco farm, where we may get a cigar rolling demonstration, then check in to our B&Bs and relax before a late afternoon stroll in this quintessentially Cuban small rural town. Our sunset shoot will be at a hilltop organic farm-restaurant.
Overnight: Private B&Bs, Viñales.

Day 6: Friday
 We’ll get up for sunrise and visit tobacco farmers to photograph them in the early morning light. We'll breakfast at one such farm before heading to another tobacco farm, whose owner is one of Cuba's most colorful and photogenic personajes (personalities), The early afternoon is free before we visit more farmers and local residents, and photograph and interact with them in and around their homes and barns. We’ll have a roast suckling pig dinner at a family “restaurant”.
Overnight: Private B&Bs, Viñales.

Day 7: Saturday
Today we’ll drive from Viñales to Trinidad, with a stop en route at the Las Terrazas ecological mountain community, or by photographing a former sugarcane community, including inside a ration store adorned with astonishing revolutionary murals. Passing through Cienfuegos, 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: Private B&Bs, Trinidad.

Day 8: Sunday
We’ll rise early for a golden hour walk, letting serendipity guide us through the streets of this magnificent UNESCO World Heritage Site, immersing ourselves in the local life as we shun the touristy quarter in favor or lesser visited quarters. The afternoon is free for you to explore Trinidad at leisure before we reconvene for a special themed shoot with a cowboy at a fantastic river venue, plus a visit to a nearby rustic former hacienda. 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: Private B&Bs, Trinidad.

Day 9: Monday
This morning we’ll journey into the Valle de los Ingenios (Valley of the Sugar Mills), a UNESCO World Heritage Site where we’ll shoot a quinceañera–a girl celebrating her fifteenth birthday–at Chris’s favorite 18th-century hacienda. We’ll lunch at a ranch farm, after which the afternoon is again yours to explore and photograph in Trinidad at leisure. This evening we’ll have an image sharing slide show before our farewell dinner at one of our favorite restaurants.
Overnight: Private B&Bs, Trinidad.

Day 10: Tuesday
Today we'll drive to nearby Santa Clara for a mid-day departure for Miami and home.