December 2-9, 2025 Street Photographer Masterclass with Steve Simon

Havana, Trinidad, Cuba Workshop Details

After some great conversations with my Cuban partner Enrique Ocana, we decided to extend our photographic geography beyond Havana and spend some time in the beautiful colonial city of Trinidad, a comfortable five-hour modern air-conditioned bus ride away. 

BEYOND HAVANA

As a photographer who first explored Havana fifteen years ago, visiting the cobblestone streets and brilliantly colored facades of Trinidad in Central Cuba reminded me of why I fell in love with Cuba on my first visit, it was mostly about the people. 

Walking the streets of Trinidad today felt like rediscovering Havana’s magic—but in a place that’s a little bit friendlier, a lot cleaner and more serene.

In Havana as with all of Cuba, the slow recovery from the pandemic has hit hard, compounding the struggles of hyperinflation, ongoing shortages of food and supplies, and even unreliable electricity. I felt a tension— a heaviness that seems to linger over daily life. 

Tourism—Cuba’s economic lifeline—is coming back slowly toward pre-pandemic levels. When you wander around Havana you do experience the warmth and welcoming of people; but you also see glimpses of struggle— in long lines at markets and homes lit by candles during rolling blackouts—and on the faces of many people.

Yet despite the difficulties there is optimism in the Cuban resilience cultivated over decades of adversity, with the unwavering hospitality that survives in tough times. This is one reason why Cuba is such a great destination for those of us passionate about capturing the people and life on the streets of the world. It’s also safe to explore even at night. 

Reminiscent of an Older Havana

When I arrived in Trinidad, I was struck by the same sense of awe that Havana gave me when I first visited. There was an undeniable vibrant energy and a raw, unpolished beauty among the colors and textures all around. Our workshop group wandered for hours day and night—capturing the fast action of locals going about their day.

Havana remains an iconic city and we all felt very lucky to experience and photograph the young dancers at Cuba’s world renown National Ballet School in Havana, a workshop exclusive. 

In smaller town Trinidad, we experienced the genuine warmth of its residents. People weren’t in a hurry to move on to the next tourist but instead would often invite us into their homes to learn about their lives and Cuban culture. It helped to have the amazing Alex Lorenzo along as our guide and translator for deeper connections and stronger more authentic pictures.

For photographers seeking a place that merges breathtaking visuals with meaningful cultural encounters, both Trinidad and Havana are outstanding places to travel to. 

Our first Havana-Trinidad Masterclass was a great experience and we learned much so we tweaked and made adjustments to elevate this edition. I can’t wait to return.

The photographers who joined us on our last workshop brought an exceptional level of talent, and we’ve decided to keep the group intimate and high-level, making this an exclusive, advanced workshop with a portfolio review requirement. If you’re interested in joining click the “Book Now” button to register your intent and we’ll provide the next steps. 

Here is  out  itinerary so far:

Day 1.   Dec 2 Tuesday. Flight to Havana.                                                        

Arrival & Orientation. 

Transfer to the Parque Central Hotel in Old Havana. 

Introductory meet and greet followed by a quick-start session with tips on shooting and editing. We will then take a photo walk with Cuban guide Alex Lorenzo along Prado Avenue as we discuss what we will see and do this week along with shooting tips and the realities of being a street photographer in Cuba.

We will end up at the water along The Malecón when the late day light should be really nice. We return for dinner at the hotel. 

Day 2.   Dec 3 Wednesday. Hotel Iberostar Trinidad

Breakfast. Early morning shoot in Old Havana- Prado Avenue. 9am-Depart for Trinidad. Stop in Santa Clara to stretch and for a street photography session.                                                     in the town center. 1pm: Lunch at a local restaurant.                                                       3pm: Continue trip to Trinidad. 530pm - Check-in at the Hotel Iberostar Trinidad                                                      730pm: Dinner at LOS CONSPIRADORES Restaurant.   

Night Shoot  in Trinidad.   

Day 3.   Dec 4 Thursday. Hotel Iberostar Trinidad 

8am: Breakfast. 9am: Explore Trinidad with our cameras.                                                 1:30pm: Lunch at a local restaurant. 230-430: We meet daily @ The Hotel Iberostar Trinidad Meeting Room for critique to take advantage of the best early morning and later in the day light. More street shooting.

5:30pm: Dinner at GIRUOP restaurant.   

Day 4.   Dec 5 Friday. Hotel Iberostar Trinidad        

Hotel Iberostar Trinidad     

8am- Breakfast. 9am Casilda Fishing Village and Beach area (4km). Street Photography inside homes near Historic district, Trinidad. 1:30- Lunch at local restaurant. 3-4:30pm Lecture & Critique in hotel meeting room.                                                  More street photography. 7:30pm: Gourmet dinner at a fine family-owned “Trinidad 500” (restaurant)

Trinidad comes alive at night and most nights we will have a street shoot with great opportunities to capture the music, dance and night life– as well as the architecture which is transformed from the daylight rendering with artificial light. Live music at the Casa de la Musica next to the Santisima Church in old historic neighborhood main plaza square.                                 

Day 5.   Dec 6 Saturday. Hotel Iberostar Trinidad    

Malia Hotel Cienfuegos                                                     

7:30am- Breakfast. 8am Trinidad Local Market shoot.                                                      9am- Drive to Cienfuegos (80km) and check in at the Melia Hotel.

11am Cienfuegos Market photograph and explore the Prado, Marti Park & Punta Gorda Area. 1130am: Board small fishing boat for the ride across the bay to Jagua Castle. Photograph and explore the local village. 1pm Lunch at the CHALILL Restaurant. 4pm- Head back to Cienfuegos to take advantage of the great light for street shoot. 6pm to 730pm. Lecture & Critique in hotel meeting room.                                                  730pm- Dinner at a gourmet Palador in CienFuegos.                                                    

Night photography in Cienfuegos. 

Day 6.   Dec 7 Sunday. Hotel Iberostar Parque Central         

Hotel Iberostar Parque Central. Early morning street photography (optional)                                              8am- Breakfast. 9am- Make our way back to Havana.                                                       11am-  Stop at Bay of Pigs to stretch our legs and it's a great opportunity for a quick shoot of the off-shore coral reef and beach. 1pm- Seafood lunch at the beach restaurant CASA EL VELERO overlooking the ocean. 2:30pm Continue travel  to Havana.

5pm Visit the park and Jesus Statue in Old Havana. 530pm Havana train station neighborhood shoot and head to Christo Square for final opportunity before check-in. 615pm Check-in at Hotel Parque Central.  7:30pm Dinner at San Francisco Square and street shoot in Armes Square. 6pm-730pm: Lecture & Critique in hotel meeting room.                                                                                                      

Day 7.   Dec 8 Monday. Hotel Iberostar Parque Central       

Hotel Iberostar Parque Central       

8am: Breakfast. 9am Location Shoot: The Cuban National Ballet School is the biggest ballet school in the world and Cuba’s most prestigious. It is a training facility and not a performance venue which means we will have great access to photograph the dancers as well as opportunities to meet with them and do portraits.

11:30-1pm. Lecture & Critique in hotel meeting room. More street photography after the meeting.                                                    

1:30pm: Lunch at Villa Hernandez restaurant outside Old Havana.                                                 

3pm: We do a tour around Havana in the classic cars  waiting for us outside the restaurant. 4pm: We get dropped off at the Cemetery in Old Havana for a one-hour shoot.  5pm: We head back to the Parque Central hotel. 530pm: Street shoot and or editing session before special workshop’s end dinner.                                            

730pm- Last Dinner of the workshop at the San Cristobal Restaurant where President Obama dined. (Reservation at that same table when available) 9pm. Very special night assignment.    

Day 8.   Dec 9 Tuesday.

Last street photography. Breakfast. Transfer to the Airport. Flight  Havana to Miami. Transfer to the Hotel Iberostar Parque Central in Old Havana. Arrival, Orientation and photowalk along the Malecon. Dinner at the hotel.                                                   

There are some changes to Cuban travel since our last visit. There is a new online immigration process that speeds things up, providing a QR code to present at the airport upon arrival. You can apply for this within 72 hours of your flight time. Our workshops are 100 per cent legal for Americans traveling to Cuba. We can't wait to see our friends and photograph in this amazing, photogenic and welcoming place. 

Most everything will be taken care of for you so we can concentrate on making amazing images of the people and the culture in Havana and beyond. We will explore vibrant, visually rich places and neighborhoods in Old Havana & Trinidad, often outside tourist areas for unique photo opportunities. 

We will visit and photograph at The National Ballet School, a Passionate Photographer Workshop exclusive. Old Havana is spectacular at night and we will go out night shooting as well.

I am very excited to work with my colleague Alex Lorenzo, a teacher and Cuban expert to bring us to the best places for photographers to wander and shoot. We are sculpting a unique photographic street workshop for you to come away with a fantastic portfolio of images. 

This inclusive trip will include most everything (except airfare): lodging at the 5-Star Parque Central Hotel in Havana and Iberostar Trinidad Hotel, most meals, transportation, transfers, daily instruction and critiques as well as your Cuban  license and all paperwork required for American Citizens to travel to Cuba. Other nationalities do not have these restrictions. Price includes a private, single room at our base hotels for the week.

Our Havana Venue: The Parque Central Hotel

We were lucky to secure rooms at my favorite hotel in Havana. Located in the center of everything, the Parque Central comprises two buildings, a colonial section and modern tower, linked by a stylish, underground tunnel. Both sections have independent lobbies, restaurants, and rooms. With the recent blackouts, it's comforting to be at a hotel with its own generator and good WIFI.

The newer tower is sleek, chic and contemporary, with a wood, glass and steel design set off by bright colors and textured fabrics. The colonial part is classic elegance: what you’d expect to find in a 5-star hotel in any global capital city. Whichever wing you stay in, you’re assured comfort and superior service. Our meeting room is also located here.

The roof terraces of both sections have pools with great views and thus great photo opportunities. Parque Central really is an oasis in the heart of one of the most densely-populated areas in Havana. The lobby might be Havana’s nicest place to chill and a great place to have a coffee or a drink while you edit your work and check your email and upload new work to social media.

The hotel is within walking distance to many of the great places we will photograph in Havana, like El Malecon by the water, and the Capital just a few-minutes walk away. It is no wonder TripAdvisor rates the Parque Central the number one hotel of 75 in Havana!

Our Trinidad Venue: Iberostar Trinidad Hotel from the same company as the Parque Central. 

Street Philosophies

Steve will be teaching you new and powerful street photography techniques guaranteed to push you from your comfort zone to new heights in your work and share his street-shooting philosophies gleaned from a lifetime of wandering urban places with his camera.

This intensive workshop will help you find your own unique vision and street style through assignments created to get you past photographic fears and cliches to capturing lyrical, poetic and decisive moments that communicate the energy of the streets. But mostly you will be shooting the theatre that is the street; sometimes together, often on your own.

All levels of photographic experience can benefit from this workshop. You’ll learn about the “rhythm of place” and you will discuss the laws and ethics of street photography as well as dealing with difficult situations that might pop up. You will define a strategy for capturing the rich daily life of people on the street; overcoming fears and shyness, approaching strangers, framing, juxtaposition, layering your compositions, letting the image come to you and whether color or black and white best suits your vision. And you will have fun!

We will have both  pre and post workshop lectures to maximize our time on the ground in Cuba. 

Workshop Video

Watch The Passionate Street Photographer Havana workshop video below to get a better idea about what the workshop entails.

Street Tech

You will talk street-tech and Steve will give you his minimalist view on gear along with a simplified shooting process to maximizing your response time to capture decisive moments. Steve’s street tools include the new Nikon Mirrorless cameras along with a carefully curated selection of lenses; but he’s familiar with a wide range of equipment to help you maximize your mirror-less, compact, rangefinder, DSLR or even your camera phone for compelling street images.

The technical is arguably the least important aspect of photography and the easiest shortcoming to fix, and as a shortcut to mastery you will talk lenses, auto focus, zone focusing, shooting form the hip, using live view, flash and a host of other tips, tricks, distractions and ideas that will improve your work dramatically. It’s a street photography workshop but the lessons learned will benefit you in all genres of image-making.

Closing The Gap...

Between where you are now, and becoming the photographer you know you can be. In class, you will look at a selection of your best work from the previous day. These daily critiques are of crucial importance, where you share ideas and constructive criticism as you look through each others’ images. The workshop will be a “safe place” for group discussions with suggestions and new ideas put forward.

If there's an interesting show going on while there, we will visit a photography gallery. We will have lectures and critiques every day. You will be encouraged to take on a theme over the week for your final portfolio and slide show. We can also provide assignments to push you to a higher level in your work.

Schedule

TBA

I always find it hard to say goodbye at the end of a workshop but I’m heartened by the fact that you leave with a renewed sense of mission and confidence, new techniques and ideas to apply and a reinvigorated passion to continue your wanderings on the streets of your world. (Plus a great portfolio of photographs!)

Your itinerary is proof of your General License authorized travel to Cuba under the general license at 31 CFR 515.565(b) for people-to-people educational exchanges.

Testimonials

Gary Niederpruem, Chicago

“What a fabulous experience. I learned more about photography in one week than I had in 5 years. Steve is very knowledgable about the technical side as well as composition. He is very patient, gives excellent feedback and will work one on one with you on any photography subject you want. I asked him for help on night photography and at 10 PM he was out on the streets of Havana with me with step by step instructions on how to take the shot. 5 star plus rating!!”

Anna Blanco, New York City

“Best workshop I’ve ever taken! Steve is not only a great photographer, he is also a terrific teacher. He is patient and very hands- on. In some workshops the instructor sends students out to shoot after a short lecture–Steve goes out with his students, coaching them throughout the process. His course is well organized and covers diverse topics. He is funny and engaging and generous with his time and knowledge. I had SO MUCH fun and am ready to sign up for the next one. Highly recommended!”

Anne Dunford, Ithaca, New York

"My week in Steve’s Street Shooting workshop challenged me tremendously. There’s nothing like taking your work apart and putting it back together with new vision to make you a better photographer. If you take this workshop, I guarantee you will see the world differently at the end."

Paul Lavergne, San Juan, PR

"Steve’s passion for photography is contagious and his teaching abilities and knowledge extraordinary! I highly recommend this workshop to anyone interested in photography."

Chapman Solomon, Mountain View, CA

“Participating in the NYC Street Photography Workshop was an enriching and exhilarating experience. It challenged me to step out of my comfort zone to improve my skills. Steve’s curriculum and hands on approach offered me an opportunity to learn new techniques, add some creativity and visualize subject matter from another perspective. Each day presented abundant photo opportunities, resulting with the capture of some amazing images, exceeding my greatest expectations.”

Stephen Sholl, New York City

"Not only is Steve a great photographer, he is also a caring, compassionate person as well. He is constantly trying to help participants achieve their photographic goals in a gentle, caring, and sincere manner. Sadly, the critiques of my work were very helpful. Steve was right-on in terms of his suggestions to better my work. The totality of the workshop was terrific, primarily because the parts were all excellent as well. Choice of shooting locations, image reviews, suggestions, videos shown, and galleries visited were all great. Steve also promoted wonderful interactions among the participants. The venue was perfect for the workshop. We could spread out, leave your things there, use the facilities, and eat the goodies provided. You know you’re in good hands with Steve! An outstanding workshop!!"

Steve Lavelle, London

"This is an outstanding workshop, led by a world-class photographer. It is impossible to spend time in a room with Steve Simon and not be inspired to get out there and make great images …I had high expectations and you exceeded them…Steve is very personable, articulate and passionate about photography, very welcoming with a warm, engaging personality. Steve’s style is outstanding. I knew of Steve from the TWiP podcast and would have attended if he was talking about how to watch paint dry…”

Oscar Piñeyro, Dallas

"I just spent the last three days with Steve Simon, What a wonderful experience, the best time spent in a workshop ever. Steve is a perfectionist, every presentation not only had spectacular photography but also the perfect music to enhance the mood, a roller coaster of emotions. He cannot hide his journalistic background every single image tells a story. His technique is flawless; his teaching patience unparalleled. I am eager to start a new chapter of my photography applying what Steve taught me in the last few days."