Plan to arrive into Miami at any time. We will meet at a great hotel near Miami International to relax, chat, and enjoy some wonderful food before flying out in the morning.

After an early wakeup we will catch a short flight from Miami to Havana, Cuba. Once through customs and with our guide, we’ll drive to our hotel in the heart of Old Havana. Shortly after arriving we will head out to explore the city, en route to lunch at one of Ernest Hemmingway’s favorite jaunts where mojitos flow and live music echoes throughout the establishment. In the afternoon we will continue exploring some of Havana’s most historic sites before watching sunset along the Malecon, the city’s most famous street next to the Caribbean Sea. Dinner will be had at one of Havana’s amazing restaurants, possibly even one owned and operated by Castro’s personal chef!

The next two days will be spent exploring Cuban culture and history throughout Havana and its surrounding villages. Each morning we will head out before breakfast to photograph the city coming alive. Fruit vendors wander the streets, fishermen bring in their catches along the Malecon, and a fleet of taxi drivers hand wash their classic cars in colorful alleyways. One afternoon we will drive just outside the city to view the gallery of artist Jose Fuster who turned an entire house into a spectacular mosaic. We will also take a short drive to see Ernest Hemmingway’s house which was left virtually untouched after he passed away. To further our Hemmingway exploration, we’ll visit the seaside village of Cojimar which was the setting for The Old Man and the Sea. It is still a vibrant fishing community today and if we are lucky, we may see huge catches coming in. In the afternoon we’ll make a pitstop at the Floridita Bar where the lime daquiri was invented for Ernest himself. Depending on the schedule back in Havana we will visit one of the city’s oldest boxing schools in addition to a famous salsa academy – each offer spectacular venues for photographs. There will be free time each afternoon to explore before heading to another wonderful dinner.

The next two days will be spent exploring Cuban culture and history throughout Havana and its surrounding villages. Each morning we will head out before breakfast to photograph the city coming alive. Fruit vendors wander the streets, fishermen bring in their catches along the Malecon, and a fleet of taxi drivers hand wash their classic cars in colorful alleyways. One afternoon we will drive just outside the city to view the gallery of artist Jose Fuster who turned an entire house into a spectacular mosaic. We will also take a short drive to see Ernest Hemmingway’s house which was left virtually untouched after he passed away. To further our Hemmingway exploration, we’ll visit the seaside village of Cojimar which was the setting for The Old Man and the Sea. It is still a vibrant fishing community today and if we are lucky, we may see huge catches coming in. In the afternoon we’ll make a pitstop at the Floridita Bar where the lime daquiri was invented for Ernest himself. Depending on the schedule back in Havana we will visit one of the city’s oldest boxing schools in addition to a famous salsa academy – each offer spectacular venues for photographs. There will be free time each afternoon to explore before heading to another wonderful dinner.

After breakfast we will hop in our bus and make our way east towards the UNESCO World Heritage town of Trinidad. During our drive we will follow the outskirts of a rainforest and as we get nearer to our destination, classic car taxis will give way to horse drawn carriages which have remained common here for hundreds of years. Trinidad is a colonial town along the shores of the Caribbean Sea where vibrantly painted houses line old cobblestone streets. It is a gorgeous place to explore and a true gem to photograph. Once checked in to our hotel, we will wander around town looking for street corner games of dominos, horse drawn carriages, and sandlot baseball games. In the evening we will retire to the rooftop bar of our hotel to listen to music and enjoy a cocktail or two before dinner.

After a morning stroll around the neighborhood, we will hop in our vehicle to drive East into the agricultural heart of Cuba. We will arrive at the Valley of the Sugarcane Mills which was once the largest producer of sugar in the world. Many of the historic structures remain and offer an interesting insight into Cuba’s past. Returning to Trinidad in the afternoon we will keep an eye out for ox pulled plows, cane workers, or other farmers to meet and photograph.

Today will largely be for travel following the beautiful countryside back to Havana. On the way we will stop for lunch in Cienfuegos, a stunning French colonial city by the sea. The afternoon will be free to explore Havana, shop for souvenirs, or savor another mojito before dinner in the evening.

We will have a full day in Havana to continue exploring this magnificent city. Depending on what we accomplished earlier in the trip, today may be spent at the Spanish Castle, visiting a boxing gym and dance school, or finding a new neighborhood to explore. We could easily spend a lifetime photographing in Havana alone, so there will always be something new and exciting to see! If the performance schedule lines up, we may have an opportunity to listen to live music after dinner.

No trip to Cuba would be complete without learning about their famous cigar industry – and there is no better place than Vinales. Vinales, a few hours drive West from Havana, is an agricultural region where small, family-owned tobacco farms are settled amongst massive limestone towers. Once here we will have the opportunity to visit a few farms to learn about their process of growing tobacco, drying the leaves, and rolling cigars. The entire process is done in the traditional way from ploughing fields with oxen to drying the tobacco in thatched huts and is amazing to see and photograph. Lunch will be had at a small farm near town, and in the evening we will retire to our hotel overlooking the Vinales Valley.

After breakfast we will visit another tobacco farm and explore deeper into the limestone formations in the center of the valley. We’ll also have some time to visit the town center before heading back to Havana. We’ll likely return to the city in the evening and will have the chance to go on one final walk around the neighborhood or along the Malecon before dinner.

Early departure to the airport to catch return flights to Miami and connecting flights home.