Santorini: Proffessional Flying Dress Photoshoot

A Santorini flying-dress shoot turns the island’s famous white rooftops and blue-domed churches into a backdrop for portraits, with photographer Yannis guiding you around Imerovigli for an hour. You choose a dress in advance, then assistant Anastasia helps you get dressed before the photo walk.

I like two things here: the private format, which gives Yannis time to help you find natural poses, and the range of dresses, with more than 30 designs and sizes up to 4XL. You also get 50 edited photos per person, plus group shots when two or more women join.

The main catch is that the advertised price does not include the dress or assistant. Budget an extra €130 for both, and remember that the outdoor route includes stairs and short walks between photo spots.

At a glance

• A one-hour private shoot: You meet at Anogi in Imerovigli and finish back at the same spot.
• More than 30 dress designs: Pick your dress and size in advance, with options up to 4XL.
• Two people make the session run smoothly: Yannis guides your poses, while Anastasia helps with the dress and its fit.
• Iconic Imerovigli backdrops: Expect blue domes, white rooftops, high-village sea views and less familiar photo spots.
• 50 edited photos per person: The photos arrive through Dropbox, with extra group shots for sessions with two or more women.
• Plan for extra costs and a little walking: The dress and assistant cost €130; transfers and makeup are also extra.

Getting ready for the Imerovigli photo walk

This is a portrait session with a walking route, not a studio shoot. You meet Yannis at Anogi, where a large square sits in front of the restaurant. The activity ends back at the same meeting point, so you do not need to plan for a separate drop-off at the end.

After booking, you receive a catalog and choose your dress and size in advance. There are more than 30 designs, with sizes available up to 4XL. Making this choice ahead of time matters: the dress is not included in the activity price, and the selection needs to be settled before the shoot.

At the location, Anastasia helps you change in a dedicated changing space. Her role is practical as well as reassuring: she helps with the dress, checks its fit and stays on hand during the session. You can arrive in comfortable shoes, then take them off when it is time to pose. The shoot is done barefoot, so easy-to-remove footwear is the sensible choice.

Yannis and Anastasia speak English, Greek and Russian. The private format is useful if you feel self-conscious in front of a camera. You are not expected to arrive knowing how to pose. Yannis offers guidance, while Anastasia helps keep the dress looking right between shots.

What the one-hour route includes

The session begins in Imerovigli and moves between photo spots in the village. The main draws are the blue domes, white rooftops and broad sea views from high points. These are classic Santorini scenes, and the flying dress gives you a more theatrical way to appear in them than a quick phone snapshot.

There are also less familiar stops along the way, chosen for an artistic touch. The exact sequence and backgrounds can vary, since the shoot happens outdoors and the route is walked rather than staged in one fixed location. Expect stairs and short distances between spots. That is manageable for many people, but it is worth knowing if you have trouble walking or would rather avoid uneven, stepped routes.

One hour is enough for several backdrops, but it is still a short session. Arrive ready to change and begin, rather than counting on the shoot to include a long break or extra time. Yannis’s pose coaching helps make the hour productive, especially if you have never had professional portraits taken.

If two or more women take part, the session includes group photos as well as individual portraits. That makes the experience more suitable for friends or family members who want both solo images and pictures together. The stated package offers 50 edited photos per person, with extra group shots for sessions with two or more women.

Why pose guidance and an assistant matter

A dramatic dress can look striking in a photograph, but getting a natural result takes more than standing in front of a view. Yannis guides you through poses, which is helpful if you are unsure where to put your hands or how to turn toward the camera. The aim is to make the pictures look relaxed rather than like a fashion shoot that you have to direct yourself.

Anastasia provides a second pair of hands. She helps you put on the dress and makes sure it fits well, so you can focus on the camera and the locations. That support is especially practical for a long, flowing garment in an outdoor setting, where the dress needs attention between shots.

The personal approach is a useful part of the private booking. Your session is not shared with another group, and the photographer can give attention to your poses and preferred shots. One couple used the shoot to mark a proposal, and the photographer and assistant helped create photos for the occasion. That is a good example of how the format can work for a special moment, though you should communicate any plans with the team in advance.

Choosing a dress and understanding the added cost

The activity costs $418 per group of up to four, but that is not the full price if you want the flying dress. Dress rental costs €100, and Anastasia’s assistance costs another €30, for a stated combined extra of €130. The currencies are listed separately, so check the total you will pay before booking rather than assuming the add-on is included.

For one person, the overall cost buys a private hour, an assistant, posing help and 50 edited portraits. For a group, the base price is shared by as many as four people, though the dress rental and assistant fee still need to be considered. Ask the provider how the dress charge applies if more than one participant wants to wear one, since the available details do not specify that.

Makeup and private transfers can be arranged for an extra charge. A male outfit is not included, and neither are unedited images or raw files. If you are planning a couple’s session, check what you want the male participant to wear and bring your own outfit.

There is a small timing detail to confirm: delivery is described as 50 edited photos through Dropbox in 16 days in one place and 15 days in another. Treat that as roughly two weeks and ask which date applies to your booking. A six-month cloud backup is also offered, so you are not expected to download the gallery the moment it arrives.

Making the most of the photographs

The photos are edited in Lightroom, and the finished set is delivered by Dropbox. That is a useful distinction if you expect a complete gallery of every frame: unedited photographs and raw files are not part of the package. Instead, you receive 50 edited images per person, with additional group photos when two or more women participate.

Think ahead about what you want the pictures to show. If you want a mix of close portraits, full-length dress shots and group images, tell Yannis before or during the session. The private setup makes it easier to ask for specific poses, though the one-hour limit means you should keep your priorities simple.

The outdoor setting is part of the appeal, but it also means you should prepare for sun. Bring sunglasses if you are sensitive to bright light, and expect to walk between locations. The dress selection happens in advance, so do not leave the choice until you meet. Comfortable shoes for arriving and easy-to-remove shoes for the barefoot photos are more useful than fancy footwear.

Who will enjoy this session most

This is a good fit if you want professionally guided portraits in Santorini’s recognizable scenery and are comfortable being photographed. It also suits a pair or small group who want private attention, matching or complementary images, and group pictures as well as solo shots.

You do not need modeling experience. The guidance is built into the session, and the assistant is there to help with the dress. The experience may also suit a proposal or another personal occasion, as long as you coordinate any special plans with the photographer.

It is less suitable if you dislike posing, prefer to keep costs to the advertised base price, or cannot manage stairs and short walks. It is not suitable for people with altitude sickness, babies under one year, or people over 95 years. The photoshoot takes place outdoors, so you should be comfortable spending the hour outside.

Booking details to check before you go

The activity lasts one hour, and available starting times depend on the date you choose. It is a private group experience for up to four people. You can cancel up to 24 hours in advance for a full refund, and the reserve-now, pay-later option lets you hold a place without paying immediately.

Before you commit, confirm the dress and assistant fee, the delivery schedule for the edited photos and any transfer or makeup costs you are considering. Also choose your dress in advance and plan to meet at Anogi, in the large square in front of the restaurant. Bring comfortable shoes and take them off when the photos begin.

Should you book it?

Book this if the dress portraits are the point of your Santorini visit, or if you want a polished set of photos from a special occasion without having to direct the session yourself. The strongest value is in the private guidance and the combination of Yannis’s posing help with Anastasia’s dress assistance. The proposal example also shows that the team can support a meaningful moment, not just a standard portrait session.

Skip it if you are mainly after a casual walk, do not want to pay for the dress and assistant, or would rather avoid stairs and outdoor posing. For the right person, the extra cost buys more than a dress rental: it buys a planned photo walk, hands-on help and a generous set of edited images. Just confirm the final price and delivery timing before you book.

FAQ

How long does the photoshoot last?

The private photoshoot lasts one hour. Starting times depend on availability for your chosen date.

Where do we meet?

Meet at Anogi in Imerovigli, in the large square in front of the restaurant. The activity ends back at the same meeting point.

Is the flying dress included in the $418 price?

No. Dress rental costs €100, and the female assistant costs €30. The combined additional charge is €130.

How many people can join?

The activity price is for a private group of up to four people. Sessions with two or more women include extra group shots.

What sizes are available for the dresses?

There are more than 30 dress designs, with sizes available up to 4XL. You choose the dress in advance.

How many edited photos will I receive?

You receive 50 professionally edited photos per person, plus extra group photos for sessions with two or more women. Unedited images and raw files are not included.

When will the photos arrive?

The photos are sent through Dropbox after roughly 15 to 16 days. Confirm the exact delivery timing with the provider, since both time frames are given.

What should I bring, and what should I know about the route?

Bring comfortable shoes that are easy to take off, since the photoshoot is done barefoot. The outdoor route includes stairs and short walks between photo spots; bring sunglasses if you are sensitive to the sun.