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December 2-8, 2024 Street Photographer Masterclass with Steve Simon & Juan Carlos Ocana

HAVANA, CUBA - A PHOTOGRAPHIC PARADISE...Join award-winning street photographer Steve Simon and Cuban photographer and guide Juan Carlos Ocana for an unforgettable week of living and breathing photography in beautiful Havana, Cuba. Click "Book Now" to be put on waitlist

  • Dates: December 2-8, 2024
  • Genre: Street Photography
  • Group Size: Max 8 participants
  • Skill Levels: All
  • Includes: American Citizens travel license, luxury accommodation, most meals and transportation

UPDATE: NEW RULES FOR AMERICAN TRAVELERS TO CUBA - It is legal for Americans to travel on this workshop! The "Education Activities and/or People To People" category is being reinstated and this is the license we travel under and the one you check when purchasing your airline ticket. This intimate six-day masterclass (limited to 8 students) will take you to some of the most picturesque, interesting and exciting locations on and off the beaten path in Havana and beyond. Shooting and experiencing Havana life is our main priority, so it helps to be comfortable. This is a premium workshop with luxury accommodation in a single room, a large air-conditioned bus with us the entire week (safe to leave gear in) and amazing food.

View All Steve Simon Passionate Photographer® Workshops Here

Havana, Cuba Workshop Details

So excited to finally be traveling back to Cuba. There are some changes to Cuban travel since our last visit. Cuba is one of the few countries in the world that manufactures its own effective vaccine and its entire population has been vaccinated and the majority boosted. Masks are optional though I recommend them indoors. Covid test are not required for entering Cuba or returning to the United States. 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 and the recent announcement by the Biden Whitehouse has loosened some of the restrictions imposed by the previous administration. 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. We will explore vibrant, visually rich places and neighborhoods in Old Havana, often outside tourist areas for unique photo opportunities. We will have great access at a local outdoor boxing club with great light–a place where some of Cuba’s best known boxers have trained.

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.

Premium Workshop in Collaboration with Cuban Photographer Juan Carlos Ocana

I am very excited to work with my friend and colleague Juan Carlos Ocana, a great Cuban photographer (now based in the US) and expert on 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, most meals (though you are free to wander off the menu), 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 the luxurious Park Central hotel for the week.

Our Venue: The Parque Central Hotel

We were lucky to secure rooms at maybe the nicest 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. 

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-minute walk away. It is no wonder TripAdvisor rates the Parque Central the number one hotel of 75 in Havana!

Street Philosophies



Steve and Juan Carlos 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!

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.

You will visit a photography gallery and participate in lectures and critiques every day. You will be encouraged to take on a theme over the week for your final portfolio and slide show. I will also be providing assignments to push you to a higher level in your work.


Day 1

  • Arrival & Orientation.
  • Transportation from the airport 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 photographers Juan Carlos Ocana and Vladimir Rivera along Prado Avenue as we discuss what you will see and do this week along with shooting tips and the realities of being a street photographer in Havana. You will end up at the water along The Malecón when the late day light should be really nice.
  • You return for dinner at the hotel.

Day 2

  • Breakfast.
  • Early morning shoot in Old Havana with local Cuban photographer.
  • You start the day with a lecture and critique. We meet daily @ The Parque Central meeting room 11:00am-1pm so we can take advantage of the best early morning and later in the day light. (Sun will rise at about 6:55 am and set just around 5:45pm). In this your first class session we will introduce participants by seeing a brief portfolio of their work and view the work of some of the best and most influential street photographers from Cuba and around the world. You are encouraged to edit and choose your top six images from that morning (and the previous day’s shoot) for critique.
  • Gourmet lunch at a fine family-owned “palador” (restaurant).
  • After the group critique we hit the streets in a trio of convertible classic cars for a drive-about throughout Havana, touring some of the most interesting and scenic places and getting a taste of what’s to come, shooting as you go with the occasional stop. You will have a local Cuban photographer accompany you each day to share their experiences and insight into photographing the streets of Havana.
  • Gourmet dinner at a fine family-owned “palador” (restaurant).
  • Night Shoot: Havana comes alive at night and most nights you will have a street shoot with great opportunities to capture the music, dance and night life in Old Havana– as well as the architecture which is transformed from the daylight rendering with artificial light. There is an unlimited wealth of photo opportunities just outside our hotel door.
  • On this night you will visit Arms Square.

Day 3

  • Early Breakfast.
  • Early morning shoot in Old Havana with local Cuban photographer.
  • Lecture, critique and meeting with local Cuban photographer. 11am-1pm @ The Parque Central meeting room. 

  • Free Shoot Time - Lunch On Your Own
  • Evening Speed Shoot: In a trio of convertible classic cars, you leave for a drive-about throughout Havana, touring some of the most interesting and scenic places in Old Havana, shooting as you go, wind in your face. You will stop at several pre-selected areas and have an hour to shoot before jumping in the convertibles and heading to the next location.
  • Dinner at our hotel: The Parque Central. 

Day 4

  • Breakfast.
  • Early morning shoot in Old Havana with local Cuban photographer.
  • 11am Location Shoot: The Rafael Trejo Boxing Club in Old Havana. This is an open air training facility that has trained some of Cuba’s world class boxers. You will have great access and great light and will meet and photograph local boxers, trainers and coaches.
  • Lecture, critique and meeting with local Cuban photographer. 2:30-4pm @ The Parque Central meeting room.
  • Gourmet lunch at a fine family-owned “palador” (restaurant).
  • Golden light street shooting in Old Havana in a neighborhood close to our hotel but away from the tourist area. Along with traditional street shooting in Old Havana, we will be meeting and speaking with local people for street portrait assignments. Time permitting, we drive to the Casa Blanca area where the large statue of Jesus is located along with vista views of Havana. 

  • Gourmet dinner at a fine family-owned “paladar” (restaurant). 

Day 5

  • 9AM Location Shoot: National Ballet School . 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.
  • Lunch & Edit On Your Own
  • Lecture and Critique 1:30pm-3:30pm @ The Parque Central.
  • Street Shooting in Old Havana. Visit a local gallery and learn about Cuba’s vibrant photography scene. 
  • Photo shoot near San Francisco square and coffee meeting. 
  • Gourmet dinner at a fine family-owned “paladar” (restaurant). 
  • Night Shoot: Havana comes alive at night and most nights we will have a street shoot with great opportunities to capture the music, dance and night life in Old Havana as well as the architectural nightscapes which are transformed with the artificial light. On this night: Prado Avenue - Cathedral Square.

Day 6

  • Breakfast.
  • Morning location shoot: Together you jump on the bus and head to several pre-selected areas for one-hour shoots. Possible locations include: The Callejon de Hamel, where vivid and colorful murals, outdoor sculptures and shrines dedicated to the Afro-Cuban religion of Santeria cover the entire small block; The other end of the Malecón; The American Embassy area, San Francisco Square and the Cigar Factory.
  • This is the final day of the workshop, and you meet 1:30pm-4:30pm @ The Parque Central meeting room for a last lecture, critique & recap.
  • Last supper and workshop wrap at Havana's best restaurant.
  • We 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.
  • Night Shoot: Optional Cathedral Square photo walk.

Day 7

  • Transfer to the airport.
  • Flight home.


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."