Oia is famous for its postcard-perfect views—whitewashed buildings, blue-domed churches, and breathtaking caldera sunsets. But beyond the scenery, Oia also offers an array of memorable tours that let you experience the island in unique ways. Whether you want to capture your trip on camera, sail around the caldera, or explore hidden corners, there’s something for every traveler. We especially love the Flying Dress Photoshoot, which offers a glamorous way to remember your visit, and the Private All-In Catamaran Cruise, which is perfect for those seeking relaxation and adventure combined. These experiences stand out for their quality, personalized touches, and the chance to create lasting memories.
In this guide, we’ll walk you through the top tours in Oia, including photoshoots, boat trips, sunset tours, and guided explorations. Each offers a different perspective on Santorini’s charm, and our detailed reviews will help you decide which fits your interests, schedule, and budget.
1. Santorini: Flying Dress Photoshoot Dress Included
At number 1, this flying dress photoshoot is a fantastic way to add a touch of glamour to your trip. For around 1 to 3 hours, you can choose your favorite dress color and be guided by a professional photographer who specializes in capturing the iconic Santorini views. The experience includes expert posing tips, ensuring you look your best against the backdrop of white buildings and the Aegean Sea. Photographers deliver between 35 and 70 high-resolution digital images, so you’ll have plenty of stunning shots—perfect for memories or social media.
What makes this tour stand out is its personalized approach. Past reviews highlight Jessica’s keen eye and helpful tips, transforming what could be a stiff photo session into a fun, relaxed experience. Guests appreciate how Jessica pays attention to details and helps find the best angles, making sure every picture captures the magic of Santorini. The option to rent a vibrant flying dress in 15 colors adds a playful, fairy-tale element—ideal for couples, honeymooners, or anyone wanting a unique keepsake.
This photoshoot is best suited for those who value high-quality images and a touch of elegance. It’s perfect for special occasions or simply capturing your trip in style. Keep in mind, availability varies, so booking ahead is wise.
Bottom Line: If you want timeless, professionally-edited photos with a dash of fashion flair, this photoshoot is a standout choice.
2. Santorini: Private All-In Catamaran Cruise, with Food|Drinks
Sailing the caldera on a private catamaran cruise offers a different perspective on Santorini. For about five hours, you’ll enjoy a tailor-made trip that includes snorkeling in clear waters, swimming in thermal springs, and relaxing on deck. The cruise also features a delicious Greek BBQ with wine, beer, and soft drinks—making it both a feast and an adventure.
What sets this experience apart is its flexibility. The itinerary can be customized—whether you want more beach time or a relaxing sail around the volcano. Many reviewers praise the attentive crew, especially Captain George and Helen, who are knowledgeable and accommodating. Guests love how the boat is kept in excellent condition, and the food is described as delicious and plentiful. The highlight for many is watching the sunset from the water, a truly unforgettable sight.
This tour is ideal for those seeking privacy, comfort, and a taste of local flavors. It’s perfect for celebrating special occasions, romantic getaways, or just enjoying a leisurely day on the water. It’s a premium experience, with a price point to match, but many consider it worth every euro.
Bottom Line: For a luxurious, customizable day at sea with excellent food and stunning scenery, this private catamaran cruise is hard to beat.
3. Oia: Santorini Photoshoot with Flying Dress Rental Option
At number 3, this photoshoot in Oia combines the region’s picturesque charm with the chance to rent a vibrant flying dress. Lasting about an hour, it includes 50 professionally-edited digital photos of your session. The photographer will guide you through some hidden photo spots and classic views of caldera, blue domes, and charming churches, ensuring you get a variety of stunning images.
The unique feature of this tour is the optional flying dress rental, available in 15 colors—adding flair and whimsy to your photos. Past clients rave about how their photographer made them feel at ease, and the results reflect a natural, beautiful style. This is a great choice if you want a quick, high-quality photoshoot that captures your time in Santorini in a fun and stylish way.
Ideal for travelers on a shorter schedule or those wanting a souvenir of their trip, this experience balances professionalism with a relaxed, fun atmosphere. The only caveat is that with a one-hour window, it’s best to book when you have tight schedules but still want quality images.
Bottom Line: If you’re after gorgeous, professionally-edited photos and love the idea of a flying dress, this is a quick, delightful way to capture Santorini’s magic.
4. Santorini 5hour Semi-Private SECRET SUNSET Tour
At number 4, this semi-private sunset tour offers a mix of scenic stops and lesser-known spots. For five hours, you’ll explore Oia, the Blue Dome Church, Profitis Ilias Monastery, and the rugged Red Beach in Akrotiri. The highlight is watching the sunset from the Military Lighthouse, where the views are spectacular and less crowded than the main sunset spots.
The tour focuses on discovering Santorini’s secret corners, away from the busiest tourist areas. Reviewers mention the guide’s patience and knowledge, making the experience engaging and personalized. The tour’s relaxed pace and scenic stops make it suitable for travelers who want a deeper, less hurried look at the island’s diverse landscapes.
Pricing is reasonable at $113 per person, making it accessible for those wanting a guided experience without shelling out for a full-day cruise. It’s especially good for those interested in combining sightseeing with a special sunset view, but it’s less suited for active travelers who prefer extensive walking or swimming.
Bottom Line: For an intimate, scenic exploration that culminates in a memorable sunset, this tour offers a peaceful, authentic taste of Santorini.
5. Santorini: Explore Hidden Gems on a Guided Tour
Rounding out our list, this guided tour of Santorini’s hidden treasures lasts about four hours and provides a well-rounded look at both top landmarks and lesser-known spots. You’ll explore Oia, Fira, and other local villages, discovering secret paths, local customs, and authentic island life.
What makes this tour stand out is its personalized approach. It’s ideal for travelers who want to skip the crowds and see the true character of Santorini. The guide shares insights into local traditions while helping you capture stunning photos of iconic blue-domed churches and scenic vistas. It’s a balanced mix of sightseeing and culture.
This tour suits travelers who want a flexible, guided experience that goes beyond the brochure images. It’s a good value for those interested in a more in-depth, authentic look at Santorini’s everyday life. The only potential downside is it might not include some of the more famous sites, but that’s part of its charm for those seeking authenticity.
Bottom Line: If you want a personalized, comprehensive look at Santorini’s authentic side, this guided tour is a solid choice.
How to Choose the Right Tour in Oia
When deciding between these options, consider your budget, interests, and how much time you have. If you’re after memorable photos and want a bit of glamour, the Flying Dress Photoshoot is perfect. For a relaxed, private day on the water, the all-in catamaran cruise offers a premium experience with flexibility. Travelers wanting a quick, fun photo session may prefer the Oia Photoshoot, while those interested in exploring the island’s lesser-known sights and sunset views should look at the secret sunset tour. Finally, if authentic local experiences and cultural insights are your goal, the hidden gems tour will serve you well.
Booking early is advised, especially in high season, to secure your preferred date and time. Think about what suits your style—whether it’s a glamorous photoshoot, a scenic boat trip, or an immersive cultural tour.
Final Thoughts
Santorini offers a wide range of tours to match every travel style. If you’re after stunning photos, the Flying Dress Photoshoot and Photoshoot with Flying Dress Rental are top choices. For those who want to explore the water in style, the private catamaran cruise offers a mix of adventure and relaxation.
Finally, if you’re interested in discovering Santorini’s lesser-known spots and local traditions, the guided hidden gems tour provides an authentic experience. Each of these tours is designed to give you a different perspective on this stunning island. Consider your priorities, book early, and enjoy every moment in Oia.
