For a recent milestone birthday, I decided I wanted to schedule a flying dress photo shoot. A popular women’s travel Facebook group had seduced me with the idea: nearly every day, I saw photos of women draped in gorgeous, flowy jewel-toned dresses with impossibly long trains smiling demurely or posing magnificently in front of a dreamy backdrop of blue-domed white structures. The comments section was agog with Yes Queens and You Go Girls.
I must have those photos, I thought.
My husband and I were going to be in Greece anyway. A trip to Santorini to celebrate my birthday made sense after meeting up with a friend in Athens. I wanted to pass my day in a beautiful place with the man I love. The dolmades and loukoumades were a fabulous bonus.
After two pandemic birthdays, a flying dress photo shoot seemed to be a rite of passage too. I would join the ranks of Seasoned Woman Travelers. I would be Feeling Myself. I would finally be the Queen for whom they Yas about. I would have these photos to look back on, remembering the year that I left my youth behind, started a business, quit my job, and moved internationally.
Typing that out now, I can see that’s a lot of pressure.
All in all, I had fun, but I did leave this experience feeling a little weird. I do like my photos, but I had a lot of expectations for this experience to be perfect, and I suspect I’m not alone in my feelings. So I thought I’d share them with you.
1. Find a photographer whose photos you like
There are lots of photographers on Santorini who do flying dress photo shoots. I found my photographer, Eduard, through Airbnb. I know that Airbnb charges vendors hefty fees, so I asked him if he had a rate for customers who book via another method. He allowed me to send a deposit through PayPal and pay the balance by cash on the day. In exchange, he gave me a significant discount. For the dress rental, assistant to toss the dress train, photographer, all unedited photos, and twenty edited photos of my choosing, I paid 260 euros. This is a risk I was willing to take, as many photographers charge hundreds (and I mean hundreds) of dollars for these shoots. Eduard was the right price and I liked his photos. There were other photographers who charged the same or less, but the quality of photos suffered.
2. Pack a strapless bra!
You need to bring a strapless bra because you’ve never tried on this dress before. Nude is preferable because you don’t know how this dress will lay on your body. The photographer will show up with your rented dress (presumably cleaned since the last person wore it) and you’ll have to make it work. You may also want to bring garment tape to hold the dress in place while you’re moving (I wish I had it for mine as the top seam kept rolling down a bit, exposing my nude bra).
3. Don’t forget cute sunglasses
Pack your sunglasses too, because those whitewashed houses reflect light like you have never seen it before. Make sure you like them; about 50% of my photos pictured me in sunglasses. At my 9:00 am shoot, I could barely keep from squinting because of the sun and the houses.
4. You’re going to sweat (a lot)
I’d also recommend bringing tissues or oil sheets (to blot sweat in the hot hot hot weather). I had to keep blotting a nice ring of sweat from my mouth (and it must’ve been visible on the photos because the photographer kept directing me to blot more).
5. Nude shoes are a good idea
Nude shoes are also a good item if you don’t want to go barefoot. Lots of other women were doing their shoots barefoot, but I preferred to wear shoes. During the shoot, I stood on a roof, ran up an old stone staircase, and hustled down the sidewalks, so it was nice to have the traction and protection. I also had gotten a pedicure before the trip, so you know, gotta keep that as fresh as possible for as long as possible.
6. Don’t bother getting your hair done
My photo shoot was in Imerovigli, a town on the side of the cliffs overlooking the water, which was breathtaking. And hot and bright. I have fine blonde hair, which promptly fuzzed and blew all around me. Had I paid to have my hair styled, I would’ve wasted that money. Of course, this my not be the case for other textures and styles of hair.
7. Expect wind
You’re going to be basically on a cliff above the ocean, so plan for it to be windy. Another reason to skip the expensive hairstylist: the wind is going to blow your hair wherever it wants and there’s nothing you can do about it.
8. Don’t bother with a professional makeup artist, either
These photos will be fairly zoomed out, as the photographer will be capturing your billowing train. I did my own makeup and had I paid someone hundreds of dollars to paint my face that I’d just be sweating off, I’d feel bad about it since I’d be mentally calculating how many gyros I could’ve bought with that money.
Many photographers will offer packages with add ons that include hair, makeup, transportation to multiple sites, etc., so just be aware of what you think you’ll really need.
9. Wax, if that’s your thing
I’m not here to body shame anyone. All I’m here to do is tell you that I was not prepared for the height of the slit in my dress. I’m 5 foot 5 inches and that slit went up to my right hip bone. I wore a nude thong to reduce panty lines and am sure that between the wind and the assistant moving my dress, I must’ve unintentionally flashed every single person who was out and about that morning, both posterior and anterior (tbh, though, the breeze wasn’t unwelcome). My photographer also had to adjust the lining of my dress quite a bit, a sort of butt flap that had rolled itself heavenward against my sweaty tuchus. He was totally professional, though I felt pretty self conscious knowing my Veet strips lie unused in my makeup bag.
All I’m saying is that if your photographer viewing your natural bikini line would make you feel uncomfortable, take care of it so it’s not a distraction on photo shoot day.
10. Flying dress photo shoots are extremely popular
Be aware that this is a hot experience at the moment. I bet I was easily one of thirty other women getting their photos taken at 9 am on a Sunday, which means you may have to wait for certain viewpoints to clear, photographer teams to pass by, and people to move out of your photographer’s frame. Most photo shoots are 1 hour and at peak times, waiting around will slow down your shoot. I imagine that if you schedule very early in the morning, this might not be an issue, but then again, it’s Santorini and I’d expect that tourists are always having flying dress shoots.
11. Choose your shoot time wisely and plan ahead
If I repeated this experience, I would opt for an earlier time, maybe even the first time slot available for the photographer. I think there would be less sun in my eyes, less sweat on my face, and a little less frenetic energy with fewer people in the streets.
Oh, and if you’re driving to your meeting point, build a big cushion of time into your schedule. I arrived a few minutes late because we didn’t account for the possibility of zero parking spaces being available, which made me anxious at the start of the photo shoot.
12. Practice your poses
I hired a photographer for one hour and that hour flew by. I had practiced poses in the mirror in the days leading up to it, but still felt a little shy and awkward on the day. Eduard instructed me on where to put my hands and how to hold my posture, but I felt intimidated. I didn’t end up doing any of the fun poses I had seen other women doing. I wish I would have stayed more present and just had fun with it, rather than letting the hustle and bustle of the environment around me make me feel awkward.
13. Have a little snack beforehand
You have one hour to make these photos happen. Most flying dress photo shoots are scheduled in the morning, so you need enough energy to get you through without passing out as you run up and down tight staircases in Santorini while trying to get to your next location before your photographer runs off to shoot another woman celebrating a milestone birthday (you’re not special). Don’t go for a heavy breakfast (no need for a food baby, unless it’s an actual baby and you’re having a maternity shoot).
14. Skip your morning coffee
For the love of goddess, do not have coffee before this shoot. Have your pancakes and joe after you’re all done. Do not waste precious minutes by frantically looking for a bathroom post-gastrin. Time is money, bb.
15. Have realistic expectations
I am not a voluptuous woman. I am a normal sized person with A cups and flat feet (hence the heels I wore — gotta pop that foot when you can to avoid looking like you have flippers!). I pretty much look how I did when I graduated high school, but now I dye my hair and slather my face with Tretinoin at night. In my mind, these photos were going to make me look different. They were going to shock me with how womanly and grown up I look. Fun fact: that doesn’t happen. All those curvy, statuesque women on the websites are not me. I did not look like them, and maybe you won’t either. You will look like you in a dress with a train. If that sounds ridiculous to you, just go google “Santorini flying dress” and just try to convince yourself that you don’t want to look like those beauties. Just try.
That said, I do love my photos. I love them because I love me. But I’d be lying if I didn’t admit that I was slightly disappointed that I somehow wasn’t transformed (through no fault of my photographer; he does lovely work). I’ve come to the conclusion that these photos are what I wanted them to be: images of me, just as I am, celebrating three decades of life in a wondrous place.
American Girl in Switzerland 