Santorini: Private Flying Dress Photoshoot & Island Pickup

Summary

Flowing dresses, caldera views and laughter with a local photographer in santorini

You’ll step into a flowing dress and wander Santorini’s iconic blue-domed streets with a local photographer guiding every moment. Expect laughter, a private changing area, and your choice of colors as you pose against caldera views. Private pickup makes it easy—and you’ll leave with 40 edited photos that capture more than just scenery.

What’s the experience like?

I stepped out of the van in Oia and honestly, my nerves were louder than the wind. Vicky—our photographer—just grinned and handed me this wild, cherry-red flying dress. She said, “Don’t worry, we’ll make it look easy.” I slipped into the dress in her little private changing spot (not glamorous but way better than wrestling fabric on a street corner). The fabric felt cool against my skin, almost slippery, and I could smell sunscreen and that salty island air. My partner tried to help but mostly just made us both laugh.

We wandered through those famous white alleys, Vicky leading the way like she’d lived here forever (maybe she has?). She pointed out which dome was actually the “real” blue one everyone wants in their photo. At one point I nearly tripped on my own hem—she caught me mid-giggle and said it happens all the time. There was this moment when she tossed the end of my dress up so it caught the wind just right; for a second I felt like some kind of movie star, even though I’m pretty sure my hair was doing its own thing. The sound of camera shutters mixed with distant church bells—funny what sticks with you.

We got to change locations (and dresses—I went for emerald next), which felt less rushed than I expected. Vicky gave tips on how to stand so I didn’t look awkward, but also let us goof around with my family in some shots. My kid tried to photobomb every picture until Vicky bribed her with a silly pose at the end. I didn’t expect to feel so relaxed about being photographed—usually I hate it—but something about the whole thing just worked. Maybe it was Vicky’s energy or maybe just Santorini itself.

Step-by-step itinerary

Day 1 — Santorini flying dress photoshoot

• Meet photographer Vicky in Santorini
• Change into flying dress in private area
• Choose dress from 15+ colors or bring own
• Visit iconic blue domes and caldera viewpoints
• Enjoy photoshoot with posing guidance
• Receive 40 edited digital photos online
• Return to original location with drop-off

Top questions

How long does the Santorini flying dress photoshoot last?

The private flying dress photoshoot lasts about 2 hours.

Is transportation included for the Santorini photoshoot?

Yes, private pickup and drop-off are included anywhere on Santorini.

Can families join the flying dress session?

Yes, up to four people can ride along and participate at no extra charge.

How many dresses can I try during the session?

You can choose two dresses from over 15 colors or bring your own outfit if you prefer.

Where do I change into the flying dress?

You’ll use a private changing area provided by your photographer—not outside in public.

Are professional photos included?

Yes, you’ll receive 40 fully edited digital images plus unedited ones upon request.

Can cruise ship travelers book this tour?

Yes, but inform your photographer at booking so pickup can be arranged accordingly.

What’s included

Your experience includes private transportation across Santorini, access to over fifteen flying dress colors (with two outfit changes), a personal assistant for making those dramatic shots work, guidance on posing from your local photographer Vicky, use of a private changing area—not public spaces—and forty professionally edited digital photos delivered after your shoot.