Real Review of a Flying Dress Photoshoot in Santorini

When I travel, I’m always looking for a unique experience or way to remember a destination. I’ve never been a souvenir t-shirt person, but I still want something to transport me back to a special place. In Santorini, I knew right away that that would be a flying dress photoshoot. The photos I had seen on social media were stunning, with incredible backdrops of the island of Santorini and impossibly glamorous models looking like Greek goddesses. I set out to find the best flying dress photo shoot in Santorini, and I’m here to share all the insider tips to help you plan your own amazing Greek island experience.

I evaluated several companies offering local photographers, and I was immediately drawn to Flying Dress because of their gorgeous photos and their practical suggestions on where and when to do a flying dress photo shoot. They clearly knew how to run a successful session and get the best for their clients. Flying Dress generously offered me a complimentary flying dress photoshoot for my honest review.

Not headed to Santorini quite yet? Flying Dress is bringing their service to Dubai as well!

I’m happy to say that from the booking process to receiving the final edited photos, my experience with Flying Dress was flawless. The booking team was responsive, prompt, and helpful, following up in the weeks leading up to my flying dress photo shoot to remind me of the appointment, set expectations, and answer my questions. They were even able to accommodate my last-minute request to change my dress color from blue to burgundy (v-neck #21).

On the day of my shoot, my photographer texted me on WhatsApp to let me know he had arrived and where to meet him. He was friendly, professional, spoke great English, and immediately put me at ease, reassuring me that everyone is a bit nervous for the first few minutes and reassuring me that he could get great photos no matter what.

The Best Place in Santorini for a Flying Dress Photo Shoot

There are several towns where most companies offer flying dress photo shoots – Oia, Imerovigli, and Fira.

I chose to do my flying dress photo shoot in Imerovigli rather than the more popular Oia at the urging of the photo team, and I am so glad I did.

Oia has tiny, crowded sidewalks, making it difficult to get a good shot without people in it. It is still the most popular choice for a photo session, and I understand why. It has many of the city’s famous blue domes, and Oia village feels like a fairy tale with its alleys and endless twists and turns – everywhere you look makes for a dream photoshoot.

I was a bit worried that Imerovigli village wouldn’t be as picturesque as Oia, but I was completely wrong. Imerovigli also has the classic whitewashed houses, birds-eye views of the caldera and Aegean Sea, and blue-domed churches that Oia is known for. It really is one of the best photo spots on the island, and I’m glad that more people don’t know about it for their Santorini photoshoot (yet!)

I got amazing photos and we had the place almost to ourselves. Santorini is a popular port of call for a Mediterranean cruise, and I was super lucky that there were no cruise ships in port on the day of my shoot. This significantly reduced the number of visitors walking around. That, combined with the early hour of my shoot, meant that most of the beautiful places where we shot were deserted. I loved that because as a people pleaser, I worried about inconveniencing other visitors as well as feeling like I was on display and being too stiff and self-conscious in the photos as a result.

The other thing that makes Imerovigli one of the best places for a flying dress photo shoot in Santorini is that Flying Dress has a small office there, making it convenient and safe to change into the dress and leave belongings behind. They locked my bag in the office, and it was located just a 2 minute walk from the first stop on our shoot. If you do your shoot in Oia, you have to change clothes essentially on the street, which will mean removing your bra in front of strangers (the majority of flying dresses can’t be worn with a bra). After birthing two children, I’m personally not very modest anymore (ha!), but I could see this being uncomfortable for many.

How Your Flying Dress Photo Shoot in Santorini Will Work

I didn’t have a very good sense of how the shoot was going to go until I got into it, so I’ll share how mine was organized to help you prepare for your own big day. I arrived at a nondescript outdoor shopping center on the instructions of Vera at Flying Dress. I was paired with a local professional photographer, who was waiting for me and he took me to a small office where the assistant was waiting to help me change and prepare.

I chose Dress #21, the burgundy v-neck dress. When you book, they will ask you to choose a size, but I found that the dress was very adjustable and will fit a variety of body shapes and sizes. The v-neck style goes over your shoulders and there is a very long fabric strap on each side that gets twisted together (almost like a racer back shape) and then wound around your waist and tied in the back. It is just two long pieces of fabric that together make up the bodice, straps, and back of the dress. Of course, all the dresses have very long trains, which make it easy to get those epic photos of your trip you’re looking for.

The skirt has an elastic waist and two high slits, which makes it easy to get that leg action in your photos. The fabric is very sheer and lightweight, so you will want nude underwear and you won’t be able to wear a bra with that style. There are some styles that support a bra, but I loved the plunging neckline look of the v neck dress.

My assistant Constantina said that red and blue were their most popular colors. I originally chose blue, but decided at the last minute that I wanted the contrast of a different color, since the water and domes and sky would be blue. I’m so glad I did! I think the burgundy turned out stunning and the contrast is perfect.

After seeing all the dresses in the collection, the gold satin was a stunning option that I hadn’t really considered. If you can pull off yellow, this one should be a contender for you. The color would coordinate beautifully with the natural surroundings, and the color is really beautiful and saturated. There are a variety of colors and styles to choose from, and the different colors means there’s something that will look amazing on everyone.

It took just a couple minutes to change into the dress, try to salvage my hair (more on that below), and head out for the shoot. We locked up the office and headed on a 2 minute walk to the first location on our photography tour, a blue-domed church bursting with bougainvillea. There were no other visitors the whole time we were at this location.

After getting all the shots we needed here, I put my sandals back on, the assistant bundled up the dress and helped me hold it off the ground, and we moved a few steps away to the next location. We shot in 5 different spots, and none was more than a 1 minute walk from the previous one. I was surprised and impressed at how many different backgrounds we could get in such a short time.

The spot where I felt most exposed and uncomfortable was when standing on a domed building. There was a sign on the building clearly saying no photos and no standing on the roof. I asked my assistant about this and she assured me that the company was friends with the owner and they had permission to be there. True? I hope so! The rule follower in me had a hard time with that one, but I went with it.

This spot overlooked a hotel where a handful of people were enjoying breakfast, and I felt like I was pretty on display here. I preferred the spots where I couldn’t see anyone watching me, but I love the unique style of photos from this spot and it was still worth the more challenging conditions.

My shoot lasted exactly one hour, and included at least 5 of the best spots in Imerovigli, with even more variety because the photographer was able to get different angles within the same location. When we were done, we walked back to the office, where I changed back into my clothes, tipped my team, and headed back to my hotel in the car that I had pre-arranged to pick me up.

I received a Dropbox link about a week later with my raw photos to review and choose my favorites for color correction and editing. After I sent in my choices for post-processing, it took 9 days to receive the final images back.

Tips for the Best Flying Dress Photo Shoot in Santorini

Though I had a wonderful photo shoot and I am obsessed with my photos, I do have some learnings that can make your session even better than mine. For the best flying dress photo shoot in Santorini, keep the following in mind:

Stick with Early Morning or Sunset

My flying dress photoshoot was at 9 am in late October. Even though the sun was rising later in the day by that time of year, I struggled with not squinting throughout my shoot. Starting at 8 am would have been better from my perspective, though it would not have had the best lighting to illuminate the buildings and caldera quite as nicely as it did at 9 am.

I asked my photographer what his favorite time of day to shoot was, and he confirmed that early morning or the golden hour were tied for the best time, and that both were better than my time and certainly better than mid-day.

Mind the Humidity and Wind

Santorini is very humid, even though it almost never rains. I say this mostly for my fellow curly-haired readers. I painstakingly straightened my hair for this photo shoot (I even packed my straightener specifically for this day!) and by the time I got to the shoot, it was already frizzing and curling. I called an audible and used water from my water bottle to scrunch it up and try to make the curls look more intentional. If there is one thing I disliked from my photos, it is how my hair looks.

If humidity negatively impacts your hair, plan carefully for how you will style it for your shoot.

During my shoot, there was no ocean breeze, but Santorini is notoriously windy. Pack a few bobby pins or a headband to give you some options if the wind picks up and you need to keep hair out of your face.

Book an Assistant to Make the Dress Fly

As part of my booking, Flying Dress kindly offered me an assistant to help make the dress fly. Constantina was essential to the success of the shoot and I can’t imagine having done it without her. An assistant is included with some photo packages, and is offered as an add-on for the entry-level packages.

Your assistant will help you get dressed, arrange the dress for the photographer, and throw it so you get that effortless flying look in the photos. I wasn’t sure how helpful this would be, but I honestly can’t imagine trying to throw it myself or having the photographer do this and be in position to get good shots. The assistant is absolutely critical to getting good photos, and I would not skimp on this one.

Plan for the Full Cost of a Shoot When Budgeting

There were a few expenses associated with my flying dress photo shoot that I didn’t consider when I originally booked and that you will want to budget for.

The first is transportation to the meeting point. If you are staying in Oia (as I was) and shooting in Imerovigli (as I did), you will need to arrange transportation to and from your hotel unless it is included in your package. It’s about a 25 minute drive from Oia to Imerovigli, and I spent about $45 USD on a car service each way through Welcome Pickups. I quoted the transfer with the company we used for a full-day tour of the island, and it would have been twice that price (but with the driver waiting during my one hour shoot). Plan for $60-$100 in transportation costs if you do not have a rental car.

The second expense to consider is tips for your photographer and assistant. My team worked hard, were helpful, helped me get tons of photos by keeping things moving and picking a variety of locations that gave us lots of different shots within a few minute walk. In short, they definitely deserved a tip. I tipped each 20 euro because that’s what I had. I could see tipping a little less for the assistant, since they aren’t doing as much as the photographer, but I went with what I had and felt it was money well spent.

Overall, what should you expect for Santorini dress photoshoot prices? Most photographers will offer more than one photography package, so you can balance a great experience with affordable prices and focus on what is most important to you. The package I had with Flying Dress was the Marilyn package, including a one-hour shoot, the dress rental, 15 color-corrected photos, 6 high-end retouched photos, and unlimited rights usage for 550 euro. As I mentioned, they included an assistant, which is typically offered with their Happy Birthday or higher packages.

​Plan for Who Will Attend

​I did my Santorini photoshoot alone, but this unforgettable experience isn’t just for solo travelers. It’s a great way to capture your love story with a partner and would make for incredible honeymoon photography. I have no doubt that Vera at Flying Dress could work with you to pull off a once-in-a-lifetime experience and include a marriage proposal in your photoshoot. 

If you do plan to include others in your shoot, let the team know ahead of time, and be sure to plan a coordinating wardrobe. Flying Dress offers group sessions if you have more than one person needing a Santorini dress rental, or you can include a partner in a few photos. Just remember that you don’t get that many final photos – between 8 and 50 depending on your package – so you will have to choose wisely how many photos you want together and how many you want alone. As my husband had no interest in photos, I decided to do this one alone. Next trip he’s not off the hook 🙂

How to Stand and Pose for a Flying Dress Photo Shoot

My photographer was great about providing guidance and direction on how to stand. I let him know that I feel awkward in front of the camera and I wasn’t sure how to look natural. He told me where to stand, where to put my hands, where to look, and more. Little tips, like to lower my back shoulder, made a huge difference in how the photos turned out.

One thing I wasn’t expecting was how heavy the dress would be when it was flying. Even though the material is very lightweight, the sheer amount of material is significant. In the beginning, I would get jerked backward when the assistant threw the dress up, which ruined the picture.

To counter this, I figured out a few ways to stand that kept me balanced and holding the desired pose. I very slightly bent my supporting leg to help me stay more stable without it being noticeable in the photos. I also learned to engage my core muscles. Those 2 things combined were enough to offset the jerk that came from throwing the dress, and I was still able to fully point my toe without balancing weight on it.

One pet peeve I had when looking at other people’s photos was that their front leg wasn’t fully pointed. As a former dancer, cheerleader, and figure skater, not pointing my toe was not an option! I knew I wanted that unbroken line in my photos, and I think they came out fantastic because of these little posing techniques that I figured out.

I will say that it’s been a long time since I danced regularly, and my calf and foot muscles were hilariously sore in the days following the shoot. If you aren’t conditioned to stand with a toe pointed for an entire hour, be sure to stretch your calves and feet after your shoot is done. I know this sounds ridiculous, but my husband and I were both laughing at how much I had to hobble around because I was so sore. Yes…I need to exercise more, and if you’re like me, you’ll want to treat this shoot like a workout or suffer for days afterward like I did.

What to Bring to Your Flying Dress Photo Shoot on Santorini

I’m not sure what I was thinking when I left the hotel, but I didn’t plan very well for what I needed to bring. To make for the best flying dress photo shoot on your Santorini vacation, you’ll want to pack the following:

  1. Small mirror for checking hair and makeup mid-session.
  2. Makeup and lipstick – I didn’t plan for what lipstick I wanted during my shoot and had to use one I didn’t think coordinated too well with my dress. Plan ahead for how you want to look and pack some basics with you for touch ups.
  3. Hair accessories – bobby pins, headbands, or small hair ties will give you options during the shoot so you can adjust to the temperature, wind, and humidity. Remember that the shots are generally pretty zoomed out, so your accessories won’t be very visible unless you zoom in on the photos.
  4. Water – even in late October, it got hot by the end of my shoot and I was super thirsty by the end of my hour.
  5. Sunscreen – Apply a layer before your shoot so you don’t get it on the dress, and have more to reapply if you’re particularly sensitive to sunburn.
  6. Flip flops or sandals that are easy to slip on and off – your photo shoot will be barefoot, but you will want to wear shoes while moving from one location to another. Slip on sandals are best for convenience – I only had sandals with a heel strap and it was annoying to have to buckle and unbuckle them every few minutes.

Wrap Up

I honestly wasn’t sure what to expect on my photoshoot, as this was the first time I have worked with a professional vacation photographer. I’m so happy to say that I had an excellent experience with Flying Dress, and fully recommend them as the best flying dress photographers in Santorini. From the pre-shoot communication to the final photos, I was impressed with the quality of the work and professionalism of the team. 

Imerovigli made the perfect backdrop for my photos, and the excellent team made the entire day a memorable experience. I now have a unique souvenir from my trip and a series of photos that I will treasure forever – I will likely never look so glamorous again!

I'm Ashley, the founder of Wanderlux and a travel junkie. When I'm not at home near Seattle, Washington, you can find me on the beach in Mexico or traveling the world. Wherever I am, I aim to travel respectfully, show my kids new things, and learn more than I teach.




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