Santorini: Private Flying Dress Photoshoot in Oia or Imerovigli

Summary

Santorini photoshoot with flying dress through oia streets and rooftops

You’ll slip into a flying dress and wander Santorini’s iconic streets with a local photographer who knows every secret corner. Expect laughter, wind-tangled hair, and rooftop views above Oia or Imerovigli. Your session includes pickup, help from an assistant, and 15-25 edited photos sent after you choose your favorites—plus that rush of doing something bold under the island sun.

What’s the experience like?

I didn’t expect to laugh so much trying on a “cloud” dress in Santorini. The fabric was lighter than I thought—almost slippery—and my photographer, Eleni, just grinned and fluffed the skirt like she’d done this a thousand times. We started near one of those famous blue-domed churches in Oia, and suddenly I was standing on a sun-warmed rooftop, the wind catching all that fabric. It was weirdly freeing—like pretending to be someone else for an hour, but also more myself somehow? Hard to explain.

Eleni knew every twisty street and where the light fell best. She pointed out a doorway painted turquoise (“stand here, trust me!”), and then helped me balance on uneven stones while her assistant kept fixing my hair between shots. There were tourists everywhere but it felt private—people smiled or waved but mostly just let us do our thing. At one point an old man passed by with his dog and nodded at us like this was totally normal. Maybe it is here.

By the end my cheeks hurt from smiling (and maybe nerves). The breeze kept tangling my hair and I probably looked ridiculous half the time, but Eleni would show me previews on her camera and—honestly—I still think about that view behind me, all white walls and sea. The whole thing took about an hour, though it went fast. Afterward we sat on some steps while she explained how I’d pick my favorite photos later online. I left with sand in my shoes and that weird happy feeling you get when you do something out of your comfort zone. Still not sure how to describe it.

Step-by-step itinerary

Day 1 — Private Santorini flying dress photoshoot

• Choose Santorini village location
• Select flying dress from 70+ options
• Explore cozy streets and rooftops
• Visit blue domed churches
• Take photos near Old Castle in Oia
• Discover hidden rooftops in Imerovigli

Top questions

How long does the Santorini flying dress photoshoot last?

The private photoshoot lasts about 1 hour.

Is pickup included for the photoshoot?

Yes, free pickup is included from Oia or Imerovigli; other locations may cost extra.

Can I choose which village for my photoshoot?

Yes, you can pick any picturesque village in Santorini as your location.

How many flying dresses are available?

You can choose from over 70 flying dresses, including unique glitter or cloud styles.

How many edited photos will I receive?

You’ll receive 15-25 fully edited photos after selecting your favorites from previews.

Are infants or small children allowed?

Yes, infants can join; prams or strollers are allowed and infant seats are available if needed.

If two people want dresses, is sharing allowed?

No, each person must book their own dress; sharing is not permitted between guests.

What’s included

Your experience includes free pickup from Oia or Imerovigli (with extra options for other locations), one hour with a professional photographer plus an assistant, use of any full flying dress from their collection of over 70 styles (including glitter or cloud designs), previews sent within 1–2 weeks for you to select your favorites, followed by 15–25 fully edited images delivered digitally after your choices are made.