If you’ve ever dreamed of snapping those picture-perfect shots against Santorini’s iconic backdrop, this private Highlights Tour combined with a flying dress photoshoot might be just what you’re looking for. While I haven’t personally taken this exact tour, I’ve researched all its ins and outs and talked to travelers who have, so I can give you a clear picture of what to expect.

What really stands out about this experience are two things: first, the chance to have professional photos taken in a stunning setting, and second, the opportunity to explore Santorini’s most photogenic spots at your own pace. The fact that it’s a private tour means it’s tailored to your interests and avoids the hustle of large groups, which is ideal if you prioritize comfort and personalized attention.

Of course, there’s a small trade-off—this experience is priced at $709 per group (up to 4 people), which isn’t cheap. But considering it includes a 5-hour private tour, a dedicated photoshoot, flying dress rental, and high-resolution images delivered digitally, many find it well worth the splurge for a truly memorable keepsake.

This experience works best for couples, small families, or groups wanting a special, picture-perfect day. If you’re looking for a way to combine sightseeing with personal photos and a bit of luxury, this could be a great fit. Just keep in mind that it’s best to book early morning or during the golden hour for those dreamy photos.

Key Points

Personalized experience: Private tour tailored to your interests and pace.
Photo opportunities: 30-45 minute professional photoshoot in a scenic, private location.
Iconic sights included: Blue-domed churches of Oia, Firostefani streets, and caldera views.
All-in-one package: Tour, photoshoot, dress rental, and digital images.
Timing: Best during early morning or golden hour for optimal light.
Suitability: Ideal for couples, small groups, or anyone wanting memorable photos.

When you’re considering a private tour like this, what you’re really paying for is a guided experience that combines sightseeing with personalized photography. Santorini is one of those places where the scenery really does speak for itself, but having a professional photographer along means you’ll walk away with photos you’ll actually want to print or share.

The tour’s pace is flexible, which really is one of its strengths. We loved the way the itinerary balances the must-see highlights with quiet, beautiful spots that aren’t always crowded. It’s clear that the guide and photographer know how to find those hidden corners while also making sure you get the best shots.

You can check availability for your dates here:

The Itinerary: What You’ll See and Do

The tour begins with a pickup from your hotel, villa, or chosen meeting point. From there, your private driver or guide will take you to the first stops—some of the most visually striking locations on the island.

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The Iconic Blue-Domed Churches of Oia

Famous worldwide, these churches are practically a postcard image. The tour stops here, usually in a location that offers the best light and privacy for your photos. Travelers often mention that the views here are particularly breathtaking early in the morning or during the golden hour, when the soft sunlight makes everything glow.

Traditional Village Streets of Firostefani and Imerovigli

Next, you’ll explore the charming lanes of Firostefani, known for colorful doors and volcanic stone streets. The quiet, authentic feel of these spots adds a layer of intimacy to your photos, especially if you’re after a romantic or family vibe.

Panoramic Caldera Views

No visit to Santorini is complete without seeing the caldera. The tour includes stops at viewpoints where you can soak in those jaw-dropping vistas of the volcanic cliffs plunging into the Aegean Sea. These are some of the most striking backdrops for your photos and memories.

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Optional Wineries or Artisan Shops

If you’re interested, you can request an extra visit to a local winery or artisan shop—an excellent way to combine sightseeing with a taste of local life (additional entry fees apply).

The highlight for many on this tour is the 30-45 minute professional photoshoot. The photographer guides you through natural poses, with a focus on making you feel comfortable and looking your best.

What makes this photoshoot special is the careful selection of a location that offers privacy, superb light, and a view—think of a quiet spot with the caldera in the background or near iconic churches, depending on the lighting.

You’ll have the choice to wear the flying dress—an elegant, flowing gown designed to look stunning in photos—or opt for a romantic couple or family shoot. Several reviews note that the photographer’s guidance results in cinematic shots that truly capture the island’s beauty and your connection.

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Dress Rental and Delivery

The tour includes a flying dress rental, so you don’t need to worry about bringing your own outfit. The images are delivered online, usually within 10-15 days, and are edited high-resolution photos. Travelers often cherish these for their quality and natural style.

This is a 5-hour private experience, including pickup and drop-off from your accommodation in Fira. The group size is limited to up to 4 people, ensuring a personal experience. The driver and guide speak both English and Greek, which is helpful for any questions or special requests.

The price, at $709, may seem steep at first glance, but it includes a good deal: private transport, a professional photoshoot, dress rental, and your digital images. Some reviews mention that everyone agrees the photos make it worth the cost, especially when you consider the custom experience and the quality of the photos.

You’ll want to wear comfortable shoes for walking on cobblestone paths, and bring sun protection like sunglasses and a sun hat. The best time for photos is early morning or during the golden hour—timings that also tend to be less crowded.

Considerations

This tour isn’t suited for people over 95 years old, and it’s not designed for large groups. Also, keep in mind that if you’re hoping to visit museums or wineries, those are extra costs outside what’s included here.

Multiple reviewers have raved about the stunning views and how the photos turned out beautifully. One said, “The stunning backdrop made the photos look like postcards,” while another mentioned how the guidance from the photographer was natural and flattering, making everyone feel at ease.

Some noted that the timing is key—early morning or late afternoon gave the best lighting. A few mentioned that the tour’s pace was relaxed, allowing plenty of time for photos and sightseeing without feeling rushed.

If you’re someone who loves capturing memories in beautiful settings, this tour offers a combination of scenic exploration and professional photography. It’s perfect for couples wanting romantic images, small families seeking keepsakes, or friends celebrating a special occasion.

However, it’s less suitable if you prefer a quick overview of the island or are on a tight budget. Also, if you’re not comfortable in formal or semi-formal attire, or if walking on cobblestones is difficult, you might want to reconsider or prepare accordingly.

This Santorini Highlights Tour & Flying Dress Photoshoot provides a uniquely tailored way to see the island’s top sights while securing high-quality, professional photos. It’s especially appealing if you want a luxurious, romantic, or family-friendly experience that results in tangible memories you’ll cherish long after your trip ends.

The combination of breathtaking views, expert guidance, and a dedicated photoshoot makes it a standout option for travelers who love to capture their adventures in style. While the price may be on the higher side, the personalized experience and stunning images often justify the investment.

If you’re after a relaxing, scenic day with a focus on creating beautiful photos—without the crowds or rushed schedules—this tour might just be the memorable highlight you’re searching for.

Ready to Book?

Santorini: Highlights Tour & Flying Dress Photoshoot

FAQ

Is this tour suitable for children?
Yes, children are welcome, and the tour pace can be adjusted to suit families. Just keep in mind that walking on cobblestone paths can be tiring for little ones.

What is included in the price?
The price covers a 5-hour private tour with a private driver-guide, a 30-45 minute professional photoshoot, flying dress rental, hotel or villa pickup and drop-off, bottled water, light refreshments, and digital delivery of edited photos.

Can I request specific locations for photos?
The photoshoot takes place at a carefully chosen location for optimal light and privacy. While the guide will select the best spot, you can discuss preferences with the photographer beforehand.

When is the best time for taking photos?
Early morning and during the golden hour (late afternoon) are ideal for softer, more flattering light.

How long does it take to receive the photos?
Images are typically delivered within 10-15 days after the photoshoot.

Are entry fees to other sites included?
No, any entry fees to museums, wineries, or artisan shops are not included and are paid separately if you choose to visit those places.

What should I wear for the photoshoot?
Comfortable clothes that suit your style, along with the provided flying dress if desired. Bring sunglasses and sun protection.

Is transportation comfortable?
Yes, the private driver/guide provides a comfortable, air-conditioned vehicle, making the 5-hour experience relaxing.

Can I customize the itinerary?
Yes, the tour is private and can be tailored to your interests and pace.

What if I need to cancel?
You can cancel up to 24 hours in advance for a full refund.

If you’re seeking a blend of sightseeing, luxury, and beautiful keepsakes, this experience is definitely worth considering. It’s a chance to make your Santorini trip truly unforgettable—both in sights and in photos.