Classic Cuba


Havana / Viñales / Trinidad


10 Nights (Fri. thru Sun.)*


6 People


Scott Fishman







Small Group Size
Top Rated Restaurants
Daily Exploratory Walks
Private Performances
1950's Classic Convertibles
Famous Cuban Photographer
Artists Studios & Galleries
Afro-Cuban Music & Dance
Legendary Boxing Gym
Santeria Religion
National Ballerinas
Organic Farm & Meal
Tobacco Farms & Homes
Cigar Rolling & Sampling
Family Pig Roast
Renowned Musicians




10 Nights Accommodations

Daily Breakfast

5 Lunches & 4 Dinners

Group Airport Transfers

Ground Transportation

Local Photographers & Guides

Admissions & Activity Fees

Cuban Tourist Visa Card

Mandatory Cuban Insurance

U.S. Government Compliance




March 23 - Apr. 02
April 6 -16
May 4 - 14

Note: Custom dates and itineraries may
be available upon request.




All accommodations are in licensed casa particulares (bed and breakfasts) with air-conditioned bedrooms, and in-suite private bathrooms with hot water showers. Accommodations are based upon a per person double occupancy rate. If you are traveling alone we will make our best effort to match you with a suitable roommate. If we are unable to do so for any reason, or if you prefer the privacy of your own room, a minimum single occupancy supplement of $295 will be applied to the cost of your trip. Single occupancy is based upon room availability and will be assigned on a first come, first served basis.



We recommend that you arrive at the José Martí International Airport (HAV) in Havana before 5:30pm on Friday (Day 0) so that you may join us in time for the Welcome Dinner. Your adventure will end in Trinidad on Monday (Day 10). Airlines currently offering service between the U.S. and Havana are: Southwest, JetBlue, American, Delta, and United. Return flights should be scheduled to depart from Abel Santamaría Airport (SNU) in Santa Clara on JetBlue or American Airlines. The group transfer to Santa Clara will be provided in the morning only. Please note that we recommend an allowance of 3 hours between connecting flights in Florida.

* If necessary, participants can arrive 1 day late and/or depart 1 day early. Contact us for details.



Domestic Airfare. International airfare. Airline baggage fees. Accommodations not in Cuba. Fees for admissions, excursions, and other events not listed on the itinerary. Meals not included on the itinerary. Guides, translators, or transportation outside of group activities. Tips for staff, guides, and drivers. Trip cancellation insurance. Personal expenses such as but not limited to: alcoholic beverage at meals, internet access, telephone calls, laundry service, and mini-bars.



You will encounter poorly maintained roads, steep staircases, dirt trails, cobblestone streets, and slight elevation changes on this adventure. All participants are expected to be in reasonably good health and able to walk several hours daily without slowing down the group.



The Cuban pace is slow and very few people speak English. You will find that poverty is abundant, goods are extremely limited, and services are sporadic. Life in Cuba can be unpredictable and unexpected circumstances will arise. Therefore, last-minute changes to the itinerary may be unavoidable and are to be expected. Patience and flexibility are necessary to enjoy your Cuban experience.



Cuba is extremely safe! It has the lowest crime rate in the entire Western Hemisphere. Violent crime is virtually non-existent and the majority of crime is classified as non-confrontational (pick-pockets, scams, and petty theft).




Arrival & Check-In - Participants shall arrange travel to Jose Marti International Airport (HAV) in Havana. We recommend that you plan to arrive no later than 5:30pm so as to allow enough time to clear Customs & Immigration, transfer to our accommodations in Old Havana, and have some time to relax before the Welcome Dinner. 

Welcome Dinner - In the evening, we kick-off our Classic Cuba adventure with a welcome dinner at one of Old Havana's top-rated paladares (privately owned restaurants). Feast on traditional Cuban cuisine and imbibe mojitos, the country's signature drink, as you become acquainted with your fellow travelers, trip leader, and local guide. We will review the final itinerary and discuss important dos and don'ts while in Cuba.

Included Meals: Dinner



Convertible Tour - Get orientated with the city, it's landmarks, and surrounding neighborhoods as we begin our day touring in classic American cars from the 1950's that are the life and soul of Cuba. Each car will be accompanied by an English-speaking guide and follow a customized route with stops along the way to maximize photo opportunities. Our tour concludes at the famous and historic Hotel Nacional where we will have drinks on the patio overlooking Havana.

Old Havana Historical Walk - The city referred to as Habana Vieja was founded in 1519 by the Spanish and designated a UNESCO World Heritage Site in 1982. After lunch, our local guide will provide historical information as we explore and photograph four main plazas: Plaza Vieja, Plaza de San Francisco de Asis, Plaza de la Cathedral, and Plaza de Armas.

Included Meals: Breakfast, Lunch



Cuban Photographer - This friend and famous photographer was part of a small group given privileged access to Fidel Castro throughout the Revolution and after. During that time, he used images to tell the stories of Cuba, the saga of its revolution, and the life of its enigmatic leader. We will meet in his home for an interactive discussion. Afterwards, you will have the opportunity to view and purchase prints from his personal collection.

Malecon - In the afternoon we'll stroll along parts of Havana's iconic esplanade that stretches for 8 kilometers along the coastline from the mouth of the harbor in Old Havana to the outlying Vedado neighborhood. The Malecon is considered Havana's living room and is where the entire city goes to meet, greet, date, and debate. Fisherman can be found along the seawall from dusk to dawn. It is also the ideal place to view and photograph amazing sunsets. There are few things more electric than nightfall on the Malecón where the city comes to life when the sun goes down.

Dinner - Enjoy a tapas style meal on the rooftop terrace of this multi-level restaurant with four distinct spaces located in a former cooking oil factory. The towering chimney still evokes the building’s industrial past, but the food and the atmosphere are all about modern sophistication. This chic and trendy venue caters to a mix of affluent young Cubans, international tourists, and the occasional celebrity.

Art & Performance Space - After dinner we head next door to the hippest place in Havana. With it's SoHo sensibility, this converted warehouse has been transformed into a huge industrial space meant to support and promote the work of Cuban artists of all branches. It has become an intellectual nexus for art exhibitions, live music, fashion shows, and invigorating debate over coffee and cocktails. This is the definitive place to experience the younger and edgier crowd that represents the emerging Cuba of today.

Included Meals: Breakfast, Dinner



Afro-Cuban Music & Dance Troupe - The Spanish imported African slaves to Cuba up until the 1880's, so it's no surprise that Cuban music and dance have deep roots in African ritual and rhythm. We have the privilege to experience and photograph up-close a private performance by a dance group regarded as one of the world's most authentic ensembles in the Yoruba traditions. The abandoned theater they call home is a decrepit yet stunning piece of architecture. Their costumes and choreography will take you on a journey of Cuban dance from the deepest Afro-Cuban roots through the beloved Latin dances of generations past, right up to the hottest salsa of today. Make no mistake about it, this special opportunity forged out of friendship is not one typically available to tourists.

Central Havana Cultural Walk - In the late afternoon we will wander far from the tourist path and go deep into the gritty and dilapidated but safe neighborhoods of Central Havana (Centro Habana) where the majority of unemployed and working-class locals live, eat, and shop. This is where you will truly experience Havana's most impoverished first hand, but also develop an understanding and appreciation of their ingenuity and pride. This is the ideal time and place for doing some street photography as you observe and interact with the neighborhood residents. Don't be surprised or hesitant when these strangers invite us into their homes to show us how they live and introduce us to family members. 

Included Meals: Breakfast, Lunch



Boxing Gym - Boxing is a passion that runs deep in Cuba and is second only to baseball. This small country dominates the world of amateur boxing and has been a consistent force to be reckoned with at the Olympic Games. In the morning we visit the oldest boxing gym in Havana to watch a group of young adults train in this tattered, world-famous open-air facility. The current head coach was a member of the national Cuban boxing team for nine years. This will be a closed session for our group with plenty of opportunities to interact with the boxers as they hone their skills.

Old Havana Cultural Walk - In the early afternoon after lunch, we'll start to explore Old Havana's narrow streets lined with overhanging balconies as we capture images of 1950's classic cars, eclectic architecture, and eccentric characters along the way. In the latter part of the day you can feel the energy in the streets build to a climax as school children play, workers head home, entrepreneurs peddle their merchandise, musicians fill the air with the rhythms of Cuba, and men engage in games of dominoes and chess on sidewalk card tables. We will engage all types of individuals on this walk. The opportunities to capture incredible images are endless and the reason why Old Havana is considered a paradise for photographers.

Included Meals: Breakfast, Lunch



Transfer - In the morning we depart for Viñales, a small rural town in the Pinar del Rio province of Western Cuba where brightly colored houses with front porches and rocking chairs line every street. The town sits on the edge of Viñales Valley, a UNESCO World Heritage Site and settlement dating back to the Spanish colonial era. Life here revolves around agriculture and offers the perfect combination of natural beauty and the country's traditional culture.

Viñales - Upon arrival we'll check in to our casa and then explore the tranquil town on foot. We'll meet many of the locals as we visit the main square, outdoor market, and outdoor stadium where school kids hone their baseball and soccer skills.

Organic Farm & Dinner - At day's end we will learn about the necessity for sustainable agriculture in Cuba on a guided walk of an organic 'finca' in the Pinar del Rio province. After the walk we'll watch the sun as it sets in the Valley of Silence before we sit down to enjoy a fresh, unforgettable farm-to-table meal and imbibe the owner's legendary "anti-stress" cocktail.

Included Meals: Breakfast, Dinner



Viñales Valley - The Valley is considered the most scenic part of the country and is famous for it's lush green vegetation, fertile red soil, expanses of tobacco plantations, and towering mogotes (limestone monoliths) that rise abruptly from the flat plains.  We start our day before dawn by photographing the Valley as the sun rises to reveal a jaw-dropping vista of the stunning landscape below.

Fields & Homes - In the early light of the morning we head down deep into the fields to photograph the campesinos (farmers) as they tend to the crops. We'll stop at many of their homes along the way to drink fresh roasted coffee and converse with family members as we learn about rural life in Cuba. Throughout the morning the campesinos and their families will gladly pose for portraits and allow us to photograph their modest dwellings.

Tobacco Farm - As the morning light begins to turn harsh, we will visit a farm that produces tobacco used in Cuba's world-renown cigars. Inside a secadero (drying house) the process of cultivating, harvesting, and curing the tobacco will be explained. 

Cigar Rolling - At the tobacco farm we'll watch and photograph a private demonstration of the the cigar hand-rolling process from start to finish. Each member of the group will receive a complimentary cigar and have the opportunity to purchase additional ones.

Pig Roast - In Cuba pig roasts are usually reserved for special occasions and holidays such as Christmas Eve. At lunch time we'll take a short drive to partake in this tradition on a farm with a family that we have very become close with since our first meeting. The warmth and hospitality with which they embrace us, along with the serenity of the surrounding landscape, always makes this a favorite activity.

Tobacco Sorting - After lunch we return to Viñales to visit a small despalillo (tobacco sorting facility) to learn about tobacco processing from field to factory for use in Cuba's legendary Cohiba, Monte Cristo, and Romeo y Julieta cigars. While there, watch and photograph the all-female workforce sort and grade plant leaves by quality and color before sending them on to the next stage of production.

Included Meals: Breakfast, Lunch



Transfer - We depart Viñales before sunrise and travel to the Sancti Spiritus province located in the center of the island. Our destination is Trinidad, a town that quickly grew from the wealth of the sugar cane industry and is now considered Cuba's best preserved colonial town, with its brightly colored buildings and original cobblestoned streets. Upon a late afternoon arrival we'll check into our casa particular located near the center of the town's historic district which was declared a UNESCO World Heritage site in 1988.

Plaza Mayor - After check-in we'll walk a few blocks to explore the beautiful Plaza Mayor in the center of the historic district and meet with the town's historian to learn about the grand structures that now serve as museums but once were individual family homes of sugar industry magnates.  

Sunset Cultural Walk - During the golden hour and sunset, we'll explore one of Trinidad's poorest neighborhoods (barrios) just beyond the historic district. Capturing Cuba has developed many friendships in this barrio full of special characters. This walk is an excellent opportunity to interact with the locals and capture some amazing portraits.

Dinner - Get ready for a fun night of dining at this rooftop paladar known for it's live music and beautiful sunset views.

Included Meals: Breakfast, Dinner



Photo Walk - We begin our day wondering through another of Trinidad's barrios and then continue on to areas outside of the historic district including the town's other square, Cespedes Central Park.

Troubadours - We'll return to the historic district for a lunch and a special performance in the home of a husband and wife duo who are world-class musicians.

Photo Walk - Afterwards we will stroll through two smaller plazas that are alive with musicians, art galleries, and the largest of the many tourist markets in town. During the golden hour, you will have the optional opportunity to climb one or both of Trinidad's main towers for gorgeous 360-degree views of the outskirts of town, the surrounding mountains, and the nearby ocean.

Included Meals: Breakfast



Playa Ancon (Optional) - Located a mere 7.5 miles from Trinidad, this precious ribbon of beach on the Caribbean shoreline is considered to be the finest arc of sand on the Southern coast of Cuba. Spending time here is the perfect way to wind down your 10-day adventure and relax before returning home to the daily grind.

Other Activities (Optional) - If you're not a beach-goer, you might want to consider exploring the abandoned plantations in the Valley of the Sugar Mills, hiking the Topes de Collantes nature reserve park in the Escambray Mountain Range, or swimming under the waterfalls at Parque Cubano or El Nicho.

Farewell Dinner - The "Farewell Dinner" will be at one of Trinidad's most talked about paladars, which offers excellent service and a diverse menu featuring generous portions of everything from lobster to pizza. We'll celebrate our unforgettable adventure together with great food, Cuban drinks, and a look back at our favorite memories.

Included Meals: Breakfast, Dinner



Check-Out & Departure - The final day includes breakfast and check-out, which concludes your Capturing Cuba adventure. Participants will then transfer as a group to the airport in Santa Clara (SNU) and depart on a commercial flight to their next destination.

Included Meals: Breakfast

* Please note that the itinerary is subject to change anytime prior to or during your adventure due to circumstances beyond our control. In Cuba it is common to experience last minute changes and cancellations. We ask for your patience and flexibility should the situation arise. Thank you.