Oia is one of the most photogenic spots on the island of Santorini, famous for its white-washed buildings, blue domes, and spectacular sunsets. It’s no surprise that many tours here focus on capturing those iconic views—whether through a photoshoot or a boat adventure. We love experiences like the Santorini Flying Dress Photoshoot because they combine professional photography with the chance to wear a stunning dress against the postcard scenery. It’s perfect for couples, honeymooners, or anyone wanting to create lasting memories in a setting that’s almost too beautiful to believe.
Oia’s compact layout makes it an ideal place for guided walks, intimate sailing trips, or specialized photoshoots. For travelers who want a mix of relaxation and adventure, options like private yacht cruises or sunset tours really stand out. Below, we’ve rounded up the top seven tours in Oia, highlighting what makes each one special—and how to choose the right one for your style and travel plans.
Quick Overview
Our list includes a range of experiences to suit different interests and budgets. For those looking to get stunning photos, the Flying Dress Photoshoot and the Santorini Photoshoot with Flying Dress Rental offer professional photography in beautiful settings. If you prefer relaxing on the sea, the Private All-In Catamaran Cruise and the Luxury Catamaran with Lunch are excellent choices, both with options for swimming, snorkeling, and enjoying exquisite Greek food. For those wanting a more in-depth exploration of Santorini’s best sights, the Explore Hidden Gems and Secret Sunset Tour provide personalized guided experiences. Finally, the Private Sailing Cruise offers an intimate, romantic way to see the caldera.
1. Santorini: Flying Dress Photoshoot Dress Included
If you’re after a truly memorable photo experience in Oia, this photoshoot is hard to beat. You get to choose your dress color and have a professional photographer capture your magic moments against Santorini’s signature backdrop of white buildings and the Aegean Sea. Plus, it’s not just about the photos—it’s about feeling like a star in a scenic film. The tour lasts between 1 and 3 hours, making it flexible enough to fit into your day.
What makes this experience stand out are the personal touches: expert guidance on posing, multiple locations, and a selection of 35 to 70 high-resolution edited photos. Guests rave about how Jessica and her team make you feel at ease, with comments praising her attention to detail and her ability to find the best spots. It’s especially ideal for couples celebrating a special occasion or solo travelers wanting to boost their Instagram game. The only downside might be the limited time, so it’s best suited for those who want a focused, high-quality shoot. Bottom line: if you want beautiful images that truly reflect your trip, this is a top pick.
2. Santorini: Private All-In Catamaran Cruise, with Food|Drinks
For around $1,514 per group, this private catamaran cruise offers an unforgettable way to see Santorini by sea. The boat is yours for about five hours, with a flexible route that you can customize. Highlights include swimming in thermal waters, snorkeling in clear waters, and relaxing on deck while soaking up the caldera views—an experience that’s hard to beat.
Guests consistently praise the crew’s helpfulness and the delicious onboard food, including a Mediterranean-style BBQ, Greek wine, and soft drinks. The cruise visits scenic spots like the Red Beach, White Beach, and the volcanic caldera, with ample time for swimming and photos. The most memorable part is the private feel—perfect for celebrating special occasions or just escaping the crowds. The reviews mention how the crew makes the experience seamless and enjoyable, with one guest calling it their “best birthday ever.” Bottom line: this cruise is ideal if you want privacy, personalized service, and a chance to see Santorini from a unique perspective. Just note that it’s a bigger price tag, but many find it worth the splurge.
3. Santorini: Luxury Catamaran Cruise with Lunch, BBQ & Drinks
This small-group cruise combines comfort, stunning scenery, and excellent food. Over five hours, you’ll sail around Santorini and Thirasia island, enjoying stops for swimming, snorkeling, and hot springs. The highlight is the Greek-style lunch buffet—think fresh salads, grilled meats, and local wines—all served onboard. The open bar adds a relaxed vibe, making it a perfect way to unwind.
Guests love the intimate atmosphere and the chance to see the caldera from different angles. The boat is decked out with comfy seating and offers plenty of space for relaxing and taking photos. The itinerary includes iconic spots like Mesa Pigadia beach and the volcanic hot springs, making it ideal for active swimmers and explorers. With a 4.9-star rating from 20 reviews, many say it’s the best way to combine sightseeing and leisure. The only caveat is that it’s slightly more expensive, but the included lunch and drinks add significant value. Bottom line: this cruise suits those who want a relaxed, scenic day with quality food and a touch of luxury.
4. Oia: Santorini Photoshoot with Flying Dress Rental Option
If you’re after a unique photography experience in Oia, this photoshoot offers a blend of professional editing and fun wardrobe options. You’ll get 50 beautifully edited digital photos, capturing your best angles in Santorini’s charming streets and caldera views. The optional flying dress rental adds a dramatic flair—available in 15 vibrant colors—that turns your photos into a fairy tale.
The photographer and her assistant make you feel comfortable, even if you’re not used to posing. Guests mention how easy it was to relax and how excited they are to see the results. The tour lasts about an hour, making it a quick but impactful experience. The standout feature is the ability to choose a flying dress, which makes your photos more memorable and shareable. This experience is perfect for couples, families, or solo travelers wanting high-quality images with a glamorous twist. The only limitation is the short duration, so plan accordingly. Bottom line: this shoot is a fantastic way to get a professional, fun-filled set of photos in Oia’s iconic setting.
5. Santorini 5hour Semi-Private SECRET SUNSET Tour
For those who want to see Santorini’s less obvious spots and catch a memorable sunset, this semi-private tour hits the spot. At just $113 per person, it includes stops at Oia, the Blue Dome, the Profitis Ilias Monastery, and Red Beach. The tour culminates with a sunset from the Military Lighthouse, offering sweeping views of the caldera.
Guests appreciate the personalized approach, with many noting the guide’s patience and ability to show them quiet, beautiful locations away from tourist crowds. It’s suited for travelers who want a relaxed pace and local insights, making it ideal for first-timers or those seeking a deeper dive into the island’s secret corners. Some reviews mention bad weather, but the guide made the best of it, emphasizing the flexibility of the experience. Bottom line: if you’re interested in a more intimate, tailored experience and love sunset views, this tour offers excellent value.
6. Santorini: Explore Hidden Gems on a Guided Tour
This guided tour offers a deeper look at Santorini’s less touristy spots. Over four hours, you’ll visit Oia, Fira, and explore hidden alleyways, local villages, and traditional sites often missed by larger groups. The tour is fully customizable, so you can focus on the sights that interest you most.
Guests rave about the personal touch and the chance to photograph iconic blue-domed churches and other authentic sights. The guide’s local knowledge helps uncover stories behind the architecture and traditions, making it a favorite for travelers who want more than just a sightseeing list. It’s perfect for those who like walking and exploring at a relaxed pace. The main drawback is the limited duration—it’s a quick snapshot of the island’s treasures. Bottom line: this tour is best if you prefer a tailored experience with local insights and a focus on authentic culture.
7. SANTORINI PRIVATE SAILING CRUISE TOUR
For couples or small groups looking for an intimate experience, this private sailing cruise offers a romantic day around the caldera. Starting from around $1,355 for up to two people, the cruise includes a private catamaran with a Greek-style BBQ, drinks, and stunning views all around. You can choose your itinerary, with stops for swimming, snorkeling, and possibly a small ceremony—perfect for special occasions.
Guests describe it as a personal, relaxing way to see Santorini, with many mentioning the quality of food and the privacy it affords. The focus on a customized, private experience makes it ideal for honeymooners or anyone wanting to celebrate with a loved one. The main downside is the cost, but for a very personal day at sea, many find it well worth the investment. Bottom line: this cruise is perfect if you want a private, romantic adventure with all the comforts.
$1,355 per group up to 2
How to Choose
When deciding which tour suits you best, consider your budget, interests, and time available. If snapping high-quality photos is your priority, the Flying Dress Photoshoot offers a quick, glamorous option. For a relaxed day on the water, both the Private All-In Catamaran and the Luxury Catamaran with Lunch provide excellent value with food, drinks, and swimming stops.
If you’re interested in a guided exploration, the Explore Hidden Gems or the Secret Sunset Tour are great for local insights and quieter spots. For a romantic private experience, the Private Sailing Cruise offers unparalleled intimacy.
Booking early is advisable, especially in peak summer months, to secure your preferred time slot and avoid disappointment.
To sum it up, Oia offers a fantastic variety of tours tailored to different tastes—from capturing picture-perfect moments to relaxing on a private boat. Whether you want stunning photos, a guided tour through lesser-known spots, or a romantic day at sea, there’s an experience for you. Consider your priorities—budget, time, and interests—and pick the one that best fits your style. With many options rated highly, you’re sure to make your Santorini visit unforgettable. Don’t forget to book early and enjoy every moment of your stay in this incredible island.