Street Photography Tips for Your Cuba Adventure—Or Any Trip, Really

After posting a few photos on my social media from a weekend trip to Cuba, friends came to me with questions about how I was able to get such ‘up close and personal’ photographs in this short amount of time. This inspired me to share my process and some personal suggestions as to how you can get better travel images from your trips abroad.

These people were genuinely just hanging out on the stoop like this, but I waited for the man to walk by to get the best composition.

1) Equipment

Let’s start here and I’m going to be real with you. If all you have is a smartphone and you really want to take excellent photos: it’s not impossible, but consider getting a nice camera. Not to say that the latest iPhones don’t have good cameras, but they will not allow you to get the quality and depth you will want from a DSLR camera with a quality lens. A decent camera could run you anywhere from several hundred dollars to thousands if you want to get fancy, so if money is tight, consider renting one for your trip—the better your camera and lens setup are, the better the quality your photos will be, and the more serious your subjects will take you. These photographs were all shot on a Sony A7 II with a Sony 24-70mm f/2.8 lens and I was extremely happy with the outcome. The A7 II is a pro camera with a phenomenal color profile and the 24-70mm f/2.8 lens is a standard range for portraits and scenes with beautiful depth of field and excellent sharpness… but it ain’t cheap (and I promise I wasn’t paid to give it a thumbs up).

I saw this boy exit this doorway and couldn’t believe the color synchronicity so I asked him to pose for me.

When in Cuba, take photos of people with cigars hanging out of their mouths.

2) Travel light and fit in

I like to be inconspicuous—it’s not usually the best idea to lug around a big camera bag filled with lenses and accessories: it can be heavy and also catch unwanted attention. All you really need is one or two lenses max with a nice range and an extra memory card and/or battery. It’s also good to not bring too much attention to whatever you’re wearing, including jewelry or other expensive looking items. This may sound obvious, but the more you dress down or look like the locals, the better they will respond to you and the less of a target you will be. If you’re a lady cakes, it may be smart to stay conservative with your attire.

I walked past this salon and decided to just walk in and ask if I could take some photos. The guy on the right jumped in the chair so he would be a part of it.

I’m pretty sure I caught these guys in the middle of flirting with each other… they weren’t mad at me capturing it.

Sometimes, perspective is everything. I like to look through cracks and doorways, you never know what lies on the other side.

t’s also good to pay attention to what’s going on in the background and to include (or exclude for that matter) subjects that may add depth to the photograph.

Ché Guevara is a central Cuban figure, so I wanted to capture an image that shed light on him. No pun intended.

Still life shots can be nice to add to the mix, just to give a sense of place.

As much of a tourist picture trap street performers can be, it’s also possible to take uncommon photos of them if you really spend a little extra time with them.

When your AirBnB host goes to this amount of trouble…

Classic cars are constantly breaking down in Cuba, this kind of scene just goes with the day-to-day lifestyle.

4) Go deeper

If you’re in a touristy city or neighborhood, consider leaving the main sites and finding areas where the locals hang out, live and work. Go to other towns nearby. Wander into places or alleyways (that don’t seem threatening) off the beaten path and try asking locals to give you recommendations or to take you into obscure neighborhoods so you can capture typical scenes and more authentic moments. If it feels right, go into shops or homes; ask the owners if you can hang out and take some pictures. Maybe get your nails done or hair cut at a local salon if you want to photograph the shop. On my trip to Havana, I wandered through several gated doorways looking for interesting subjects and, with some luck, I stumbled upon a colorful outdoor gym where some guys were working out, an impoverished brothel, and a boxing ring where a group of kids were practicing. Getting images like that would be impossible if you didn’t put yourself out there to explore deeper. Just be careful and know where your limits should be drawn.

Exploring neighborhoods outside of the main tourist areas—even if they seem desolate and scary at first—can get you shots that most tourists don’t have. Just be careful

I stopped to watch the kids play, and at first they were wondering why, but eventually they stopped paying attention to me and that’s when I was able to capture the moment more genuinely.

I wandered into a gated area into this colorful gym and followed this man around for several minutes, capturing him working out. He probably thought I was crazy, but I just smiled and he let me.

The teacher of this group of kids let us take photos of their boxing class for a little extra cash.

I wandered into what seemed like a brothel building and was ushered by two women to the home of this older woman who told me about her financial problems and illnesses.

I asked our driver who took us to Viñales to take us to a tobacco plantation that was not touristy, as some of them can be. It’s always a good idea to let the people who are guiding you know that you are interested in local things so they don’t automatically bring you to the most touristy locations.

5) Be confident and fearless

Being confident goes especially if you’re a woman traveling in a place that may feel male-dominated and where you really have to hold your own. The key is to remain cool, collected and to not care what people think. Handicaps lie in fear and in worrying about people’s judgments or of getting rejected. You will probably get stared down or shooed away at some point on your trip, and that just goes with the territory, but with owning it lies great power. If you are confident and brave, while still remaining kind and caring, your subject will feel comfortable with you and give you the power to direct them, should you want to. When you have conviction, it’s easier to move people to more aesthetic backgrounds as well as encourage them how to pose, without being obnoxious or invasive. With that said, it’s important to feel out your limits and not overstay your welcome.

took several photos of this girl and she was NOT having it. I just smiled and played dumb, and got my shot.

You notice the strangest things when you’re actively looking… This was literally just a room off a main street with 3 red sofas in it and a guy hanging out.

These guys were not even posing, they just looked like that! So, I poked my head in through the window, smiled and started taking photos, hoping they wouldn’t beat me up.

This man was really not happy with me taking his photo. At first he was reading the paper, and then as I continued to take photos, waiting for him to look at me, he eventually dropped his paper down and gave me the stare of death. That’s when I left…

6) Connect with your subjects

Talking to my students over the years, it seems that one of the challenges that often comes up is shyness and fear of asking people to pose. It’s normal that going up to strangers may seem uncomfortable, but if you turn the fear into excitement and just realize that people don’t bite, it will be easier, especially if you manage to truly connect with your subjects. Smile, laugh, flirt if you have to, be silly or act stupid if you think it’ll ease up the interaction. Be genuine and genuinely interested in what they might be doing. Ask questions if you’re able to communicate adequately. People are immediately attracted to or put off by others’ energy, so you’ll want to have the kind of vibe that makes people comfortable around you. If you are entering into impoverished areas, be compassionate and empathetic towards people’s needs. Try to always ask your subjects if you can photograph them, unless you are going for a candid moment and if you have gifts, food or small change, consider giving your subjects something in exchange for taking their photo. In some countries, this is expected. Also, you should show them the photo(s) you just took and tell them how wonderful they look. Overall, genuinely connecting with your subjects is most important if you want to get deeper images.

I walked up to this man and started asking him about the watches he was repairing. We quickly made friends and then he let me take all sorts of photos of him from all different angles. I liked his facial expression here best.

This man stole my heart. If I had been able to speak Spanish better, I would have loved to listen to his story. I especially wanted to know why he was wearing two watches

My friend and I hung out with this guy taking photos of him for at least 5 minutes as he made a sale to a little old lady. He was very excited that we were showing so much interest in his pig.

7) Get creative and be prolific

Shoot, shoot shoot and don’t stop at one photograph and at one perspective. If you have the time and available memory, why not take several photos of the same subject? I like to play with composition, angles and pose, so that I walk away with options. The same scene can be shot in infinite ways, and you can only do better if you try different perspectives. Get creative: look for reflections, shoot through things, shoot from above, from below, turn your subject into the light or away from the light, shoot wide, shoot close. Working your creativity will serve your images and will teach you to become an overall better photographer.

I like to shoot the same photo from several different angles and with different focal points. You never know what’s going to end up looking best.

I’m always paying attention to reflections, mirrors and such as they can really embellish a composition or perspective.

This woman let me take several photos of her and her son, and as I got closer I noticed the man in the background, which made the scene all that more interesting.

shot this from the backseat of a taxi, as I noticed all the reflections going on in the window, and took several, patiently waiting for the most interesting juxtaposition to happen.

Sometimes, if you find objects in the foreground that you can shoot through, you end up with much a more compelling composition.

By hanging out and taking several photos of same scene, you can capture completely different energies and images.

8) Be aware, patient and passionate

I could not stress this one more: the best photographers are those who remain aware and patient. Keep your eyes wide open at all times, your camera ready, and be a committed observer of your environment. Go the extra mile for your photography. Watch what people are doing closely and their interactions, look up, look down—you never know what is right under your eye that you don’t quite see, and also, wait for things to happen. The famous National Geographic photographer, Steve McCurry, gave me this insight a long time ago: if you find a beautiful mural or an attractive landscape, but nothing interesting is going on right then, then wait for it to. Stand there for as long as you can take it until something worthwhile takes scene, and if you’re not happy with that, then wait some more.

I noticed this little scene and stood there waiting for some sort of interesting vehicle to pass by so I could get more of an action shot. At times I don’t even put my camera to my face until I see the moment about to happen, so that it doesn’t change people’s attitudes.

I stood there patiently waiting for the most beautiful classic car I could find to pass by.

I stood here waiting for people to walk by for a decent amount of time, hoping I’d get the best composition.

This boy was just hanging out against the wall and I knew if nothing else was going on that it wouldn’t be as exciting of a shot, so I waited for a bit until something happened in the foreground. It’s also important to be quick to shoot, because moments can be quite fleeting.

9) Follow the light

Light can make or break a photograph. Broad sunlight is typically going to be harsh and offer dense shadows, which could be exactly what you’re going for or could ruin everything. There are no solid rules in my opinion about when to shoot or not shoot, but there are definitely ways to interpret and follow light appropriately so that you can capture what speaks to you most. Of course, sunrise, sunset and diffused light can be softer and more attractive, but don’t get discouraged if you can’t shoot during those times, there’s always a way to produce excellent imagery with the given conditions: it’s just a matter of trial and error and paying attention to what works best for you.

Don’t be mad at harsh light and shadows, sometimes they make everything about a photo.

I’m always looking for interesting displays of light, especially when it highlights subjects in uncommon ways.

Light is very important when trying to get great photos of monuments and landscapes. Remember, these places have been photographed over and over and over, so if you want to capture something different and better, it‘s a good idea to visit them at an attractive time of day.

10) Editing and retouching

A good photographer knows that sometimes it takes another set of eyes to edit photos. Consider showing your first batch of selects to one or several people and get their opinions. Sometimes, we tend to fall in love with a photograph because of the memory we had while taking it, but it may not necessarily be the best shot. If there’s something I’ve learned from top photo editors, it’s ‘less is more’ when making edits, and only show your best work: your photos are just as good as the least compelling image.

Secondly, if you have a photo editing software such as Photoshop, Lightroom or any others, they can be your best friend. A photograph straight out of the camera can definitely be wonderful, but a little bit of doctoring can go a long way. Perhaps in a photo you took, the light was just too harsh and there weren’t many great colors around anyway, so consider popping the image into black and white and see what you get! Or, saturate the colors a little to make a photo pop. Crop in if you didn’t take the best composition, and maybe try several different crops to see which looks best. Nowadays, you can download plenty of filter presets for Photoshop or Lightroom which can also allow you to stylize photographs in one click and give your images a different feel. With that said, be careful to not overdo it, sometimes over-Photoshopping or intense presets can downgrade the professional quality of an image.

I edited this image a little differently than I normally do by moving around some of the saturation and giving it a slightly more vintage feel.

I boosted the saturation on this shot to make the meat pop more.

Because of the harsh shadows and uninteresting color that was going on in this image, I switched it over to black and white, which gives it a more timeless vibe and forgives the lighting better.

11) Have fun!

Overall and most of all, have fun! Photography is not meant to be stressful or scary and traveling is supposed to be liberating and enjoyable, so please make the most of your trip and don’t worry too much about getting the world’s greatest travel photo—Steve McCurry is busy doing that for us all! The people you connect with and the wonderful moments you share are what are most important, in my opinion, and the photographs are merely physical means to remember them.

I’d love to see what you capture… if you feel inspired, shoot me an email at info@ericasimone.com!

To see more of my work, check out my website www.EricaSimone.com 

This article originally appeared in Huffington Post’s Contributor Platform.

Me doing my thing by ©Daniel McKnight