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Why You Should Book a Puerto Rico Photographer for Your Vacation

Why You Should Book a Puerto Rico Photographer for Your Vacation

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Planning a trip to Puerto Rico and want to get awesome Puerto Rico photos? Keep scrolling to find out how to book a Puerto Rico photography session at an affordable price!
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When I planning a trip to Puerto Rico with friends, I knew I wanted to get really cute photos of ourselves without bringing a tripod.

So, I booked a professional photographer in Puerto Rico to take gorgeous photos of our group exploring picturesque Old San Juan. It was super easy to book and we had a BLAST during the shoot!

Keep scrolling to see what happened during our vacation photography session to see if it’s right for your next trip to Puerto Rico!

Don’t want to scroll? Click HERE for $25 off a Flytographer photoshoot!

Don’t have time to read a bunch of Puerto Rico blog posts and reviews? Here are some of our top picks for visiting Puerto Rico.

Popular Puerto Rico Tours/Activities

Where to Stay in Puerto Rico

Is Puerto Rico Vacation Photography Worth It?

This was my first trip to Puerto Rico and I knew I didn’t just want a phone full of selfies. I mean, that also happened, but I wanted to truly capture some beautiful moments with my friends.

If you’re like me and take lots of photos of other people, hiring a photographer is a great way to actually get IN the shot.

Plus, the photos turn out so much better than when you ask a stranger on the street. I mean, I think we’ve all been there!

Our Puerto Rico Photoshoot in Old San Juan

We met with our photographer Karlota in Plaza del Quinto Centenario in Old San Juan in the evening to take advantage of Golden Hour.

Fun fact: We actually went there earlier in the day for a food tour where we learned that the big totem pole in the plaza was built by Spain to commemorate the 500th anniversary of Spain conquering Puerto Rico.

She asked us if there were any specific spots we wanted photos and we told her about a gorgeous magenta building that was right next to the plaza that we all fell in love with. So, that’s where we started!

Image of 5 women in front of a magenta pink building in Puerto Rico
Photo credit: Karlota with Flytographer

Karlota might be my new favorite photographer because she made us all feel so relaxed, comfortable, and confident. She also knew exactly how to pose us for the best results (and she mixed it up for all the solo shots so we didn’t all do the same poses).

We walked along the cobblestone streets that were filled with colorful buildings. She was really skilled with avoiding crowds so we could take our time getting the perfect shot.

Image of 5 women walking down a cobblestone street in Old San Juan Puerto Rico
Photo credit: Karlota with Flytographer

The pace of our photo shoot in San Juan was nice and relaxed. And we got to explore areas of Puerto Rico that we might not have had time to explore on our own.

Plus, we got to get to know Karlota and hear more about her life in Puerto Rico.

Click HERE for $25 off a Flytographer photoshoot!

Why You Should Hire a Puerto Rico Photographer Through Flytographer


We’ve used Flytographer all over the world and they ALWAYS know the best photo spots. It’s often someplace that I wouldn’t have found myself but the photos turn out awesome.

Image of a woman posing in the doorway of a fort in Old San Juan Puerto Rico
Photo credit: Karlota with Flytographer

Karlota took us to a little historical area where we got cool photos in the doorway plus she knew exactly which street to go to for the cutest photos of building and ocean.

And we were able to ask her for restaurant recommendations, activity ideas, as well as what resorts are worth staying at during our next trip.


Usually, I travel with my family and I spend a lot of time trying to get them to look “normal” in front of the camera that I don’t have time to think about how I look. Well, I mostly look frazzled!

So, using Flytographer is awesome because the photographers help me figure out where to look and what to do with my hands so I don’t look so awkward.

Image of a woman in a red dress posing on a bench in Old San Juan Puerto Rico
Photo credit: Karlota with Flytographer

The photographers with Flytographer always know just what to do with me. And I’m so appreciative!

After I saw the photos from our first Flytographer shoot, I realized how much of a difference their expert guidance made.

And some of my favorite photos are when they have me do activities during the shoot so I look natural and spontaneous.

Book a Family Photo Shoot

Whenever we travel, we almost always book a family photo shoot with Flytographer. They are super easy, affordable, AND guarantee that I’ll be in some photos. You can get $25 off if you book through this link or use the code HAWAIITRAVEL.


I used to always bring my “big” camera with me on trips (especially when it was the first time I’m visiting) because I want to get lots of good photos.

However, I usually end up lugging it around but using my phone instead because it’s so much faster (and I’m so used to taking a gazillion photos on my phone).

Sometimes I even travel with a tripod because I have lofty expectations of being in all my photos. That just doesn’t happen.

Booking a Flytographer photo shoot sort of lets me off the hook. I know I’ll get “nice” photos without having to do the work.


I always say that activities are only fun if the people around you are enjoying themselves as much as you are.

That rings true for working with a vacation photographer in Puerto Rico.

Image of 5 women throwing straw hats up in the air in front of a yellow building in Old San Juan Puerto Rico
Photo credit: Karlota with Flytographer

We did a lot of group shots of us pretending to be drunk while linking arms and walking down cobblestone streets. And we all threw our hats in the air. The laughing in the photos was genuine because we all felt silly together!

Click HERE for $25 off a Flytographer photoshoot!

Top Puerto Rico Photography Spots

Old San Juan

If you love colorful buildings and cobblestone streets, this is the place to go! It’s the colonial section of San Juan and it has a cool mix of city, historical forts, and ocean views.


Another place to get beautiful vacation photos is the traditional neighborhood of Piñones. It’s on the beach but you can also walk around food booths and see street art.


Another beachy area for beautiful photos is the Condado neighborhood. Here, you’ll stroll around fancy shops, exciting nightlife, and a stunning beach.

How to Book Affordable Puerto Rico Photographers

While we’ve used a lot of different vacation photographers throughout the years, some of my most memorable experiences have been through Flytographer.

Basically, it’s a concierge vacation photography website where you can find photographers almost anywhere in the world, including Puerto Rico. That’s how we found Karlota. Find the best prices here.

Image of 5 women sitting on old stairs in Old San Juan Puerto Rico
Photo credit: Karlota with Flytographer

Flytographer makes it really simple to pick the perfect Puerto Rico family photographer. You can find out all about their photography style, secret places to take photos, and even scroll through their online portfolio before you book your shoot!

And Flytographer’s booking process is simple and quick — just pick your preferred dates with a click of a button.

They will then check availability for you so that there’s no stress involved in selecting an available date or time slot when they get back to you with more information on what works best for them!

What I love most about Flytographer is that they are FAST! We sometimes receive our photos before the end of our trip! I love looking at them on our flight home.

What to Wear for Puerto Rico Pictures

Of course, you can totally wear whatever you want for your Puerto Rico photos. We had a group text where we shared our outfits and ended up with a mix of bright and neutral colors.

Image of 5 women wearing dresses walking down a street in Old San Juan Puerto Rico
Photo credit: Karlota with Flytographer

I’m listing a few wardrobe options to add to your Puerto Rico packing list to make your photos look cohesive.


If you are doing your Puerto Rico photography session in Old San Juan or by the water, a nice color palette is pastels.

For Caribbean locations, we usually do a variety of pastel pink, baby blue, seafoam green, pale yellow, and light purple. It’s fun to mix and match.

Bright Colors

When I think of Puerto Rico, I think of vibrant colors. For this photoshoot in Old San Juan, we decided to include some bright colors.

I actually brought a purple dress that I wore for our Cabo photoshoot, a tropical maxi dress, a bright blue tropical dress, and the red tropical dress I ended up wearing.


Another option is to stick with neutral colors. This works well if people wear a combination of white, tan/khaki, and blue. It makes a nice contrast to the vibrant background.

All White

We happened to do our photoshoot in San Juan near a couple doing wedding photos and their white outfits totally popped against the colorful backdrops.

I could see couples or families doing all white for some really beautiful photos.

5 Tips for Getting Awesome Puerto Rico Pictures Every Time


I want to point out that Puerto Rico is super humid, so you’ll want to take that into consideration when thinking about your hair and makeup.

Image of a woman wearing a red dress in front of a magenta wall in Old San Juan Puerto Rico
Photo credit: Karlota with Flytographer

I know it can be tricky to look your best after a day of snorkeling or cruising, but it really helps if you can take a few moments to “clean up”.

You can either plan to go back to your hotel to freshen up or block out some time to head to a local restroom so you can re-apply your makeup and re-do your hair.

I brought along my 3-Day Bender curling iron and my hair did okay for most of the shoot. But others had their hair fall flat pretty quickly.


I know that I just gushed about Flytographer’s posing abilities, but I always think it’s a smart idea to have as many tools as possible.

That way, you’ll have a few solid “go-to” poses you can try out when you need to change things up.

One of my friends suggested watching posing videos on YouTube to help us figure out simple poses that still look natural yet confident!

This is one of my favorite posing videos because it breaks down a few easy poses that anyone can do.

Watching how-to pose videos has helped me figure out what to do with my hands, where to look, and how many ways there are to flatter your body.

Not only that but you can get ideas on how to interact with your kids or friends on camera so it looks carefree.


If you are doing a family photoshoot in Puerto Rico, don’t forget to ask for a few photos without your kiddos.

I always make a point to let our vacation photographers know that I want to make sure to get a few shots of just me and my husband. These usually end up being some of my favorite photos.

When we come back to Puerto Rico with my family, that’s exactly what I’ll be doing.


One of the most important things that you can do for your Puerto Rico photographer is to make it clear what you envision for the shoot. This includes the photography style and family combinations.

Image of 5 women in front of a fort in Old San Juan Puerto Rico
Photo credit: Karlota with Flytographer

Flytographer asks a lot of great questions before your shoot to get you thinking about what you’re looking for, so that way your photographer will be on the same page as you.

You’ll also want to think about your photo location and if you’re picturing something specific (like walking on the beach or getting shots with a colorful wall).

If you’re a visual person, it can help to scroll Instagram and create a folder of your favorite photos of OTHER families so your photographer can help you replicate some of the ideas.


One last tip for getting the best Puerto Rico photos is to include props.

I forgot to pack a hat for Puerto Rico so we ended up stopping at a little shop and found large-brimmed hats that said Puerto Rico in sequins.

Image of 5 women holding Puerto Rico hats
Photo credit: Karlota with Flytographer

Obviously, we had to buy ones for the entire group to use for our photos!

We wore them, held them, and even threw them up in the air for some of our favorite photos!

Booking a Professional Photographer in Puerto Rico FAQs

How do I find a reliable photographer in Puerto Rico?

Look for photographers with good reviews and portfolios showcasing their work. Websites, social media, and professional directories are good places to start. I highly recommend using Flytographer because all their photographers are vetted.

How far in advance should I book a photographer?

This can depend on the time of year, but generally, 3-6 months in advance is recommended, especially for peak season. We booked our photographer about 2 months out because it was shoulder season.

What’s the average cost of hiring a photographer in Puerto Rico?

Prices can vary greatly based on the experience level of the photographer, the length of the shoot, and the type of event. However, you might expect to pay anywhere from $100 to $400 per hour. Flytographer shoots range from $285 (for a 30-minute session) to $538 (for a 90-minute session) where you get digital copies of the photos.

Do photographers in Puerto Rico speak English?

Yes, many photographers in Puerto Rico speak English. Puerto Rico is a US territory, and English is widely spoken.

Will the photographer provide props for the photoshoot?

This varies from photographer to photographer. Some may provide props, especially for themed shoots, while others may not. It’s always best to discuss this beforehand. I highly recommend bringing your own.

What is the most photographed site in Puerto Rico?

The most photographed site in Puerto Rico is often considered to be “El Morro,” or the Castillo San Felipe del Morro. El Morro is not just a photogenic site; it’s also a UNESCO World Heritage site and a symbol of Puerto Rico’s rich history.

Photographers in Puerto Rico Wrap Up

Get your Puerto Rico photos taken by one of the best photographers in the area.

Check out our list of recommended photographers in Puerto Rico and book a shoot with them today!

Remember to wear something you feel confident in so you can have an awesome photo session in Puerto Rico. Make sure to follow these tips for getting perfect pictures, too!

Check out these awesome Puerto Rico family photographers! Click HERE for $25 off a Flytographer photoshoot!

Looking for more Puerto Rico travel resources? Check out this guide to island hopping in Puerto Rico, tips for visiting Puerto Rico for the first time, Puerto Rico resorts for families, Hawaii vs Puerto Rico, and how to explore Puerto Rico with kids!

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