If you’re heading to Greece and want to make the most of your limited time on Santorini, a private, customizable tour like this one from My Santorini Tour could be just what you need. Designed to give you the freedom to pick your highlights while still enjoying a guided experience, this tour offers a flexible way to see the island’s top sights in about five hours. It’s perfect if you prefer to avoid big tour groups and want a more tailored approach to your sightseeing.
What really caught our eye are the ability to customize your itinerary and the chance to visit both well-known spots and hidden gems. Plus, the inclusion of a local winery visit for wine tasting adds a uniquely authentic touch. However, one thing to keep in mind is that the tour is not suitable for travelers with mobility issues, so if you or someone in your group has difficulty walking, it’s worth considering this aspect.
This tour seems best suited for travelers who want a personalized Santorini experience without being tied to fixed schedules. It’s especially attractive if you’re eager to see the highlights but also crave some flexibility and local insights. Now, let’s walk through what makes this tour stand out — and what you should consider before booking.
Key Points

- Flexible and customizable: You can tailor your itinerary based on your interests and pace.
- Comprehensive sights: Visit iconic spots like Oia, Megalochori, and the highest point at Profitis Ilias.
- Authentic experience: Includes a visit to a Greek winery with wine tasting.
- Convenient: Pickup and drop-off from your accommodation or airport included.
- Private guide: Enjoy personalized attention and local tips.
- Duration: Perfectly timed for a quick yet in-depth look at the island’s highlights.
Why Choose a Private, Tailor-Made Santorini Tour?

Santorini is a small island, but it’s packed with sights and experiences. This tour recognizes that everyone’s interests are different, which is why the customization aspect is such a big plus. Instead of following a rigid schedule, you can tell your driver-guide what you really want to see, whether it’s the famous whitewashed villages, the volcanic beaches, or the scenic viewpoints.
The tour lasts about five hours, which is enough time to get a taste of several key locations without feeling rushed. The private guide means you can ask questions, get personalized recommendations, and avoid the crowds that usually flock to the island’s most popular spots. Plus, the included bottle of water and transportation make things comfortable during the day’s adventures.
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What’s Included and How Does It Work?
The tour kicks off with pickup from your accommodation or a designated location, which is a huge convenience. You’ll meet your driver-guide, who will help craft your itinerary. Whether you want to follow a pre-designed route or go off the beaten path, your guide will accommodate your wishes. This flexibility is perfect if you’re short on time but want to maximize your experience.
You’ll explore some of the iconic spots like Oia, with its signature white houses and sunset views, and Megalochori, a charming village less visited by crowds but filled with character. The tour also takes you to Kamari and Perissa beaches to relax at those famous black sand shores, ideal for a quick dip or just soaking up the scenery.
At the highest point of the island, you’ll visit Profitis Ilias Monastery, which offers panoramic views and a chance to learn about local history. Then, for a taste of local life, you’ll visit a Greek winery cellar to understand the wine-making process and sample some regional wines.
The Itinerary: How Flexible Is It?
While the tour provides a suggested route, the real charm lies in tailoring it to your preferences. Want to spend extra time wandering around Oia? Or perhaps you’re more interested in discovering lesser-known spots? Your driver-guide can steer the day accordingly. This is a big advantage over organized group tours, which often follow a strict schedule.
A review from a traveler highlights the flexibility: “Our guide took us off the beaten path to some hidden viewpoints, which made our experience so much richer.” On the flip side, some may find the 5-hour window tight if they want to see everything in detail, but it’s ideal for a quick, curated overview.
The Wine Tasting Experience
Visiting a Greek winery isn’t just about tasting wine; it’s about connecting with local traditions. The cellar visit provides insight into how winemaking has been part of Santorini’s culture for centuries. Expect to learn about the unique volcanic soil that gives Santorini wines their distinctive character, and enjoy a sampling of regional varieties.
From reviews, the wine tasting is considered a highlight: “The winery was small but authentic, and the owner was passionate about sharing their craft. It felt like tasting wine with friends.” It’s a great way to relax after sightseeing and adds a special, authentic touch to your tour.
More Great Tours NearbyWhat Travelers Say
Most reviews mention the excellent communication and flexibility of the guide, with many appreciating the personalized service. Travelers also note that the timing and transportation are smooth, making the day comfortable and enjoyable. A few point out that it’s not suitable for those with mobility issues, as some locations involve walking on uneven surfaces or stairs.
Price-wise, the $198 per person is reasonable for a private, tailored experience that includes transportation, guide, and wine tasting. If you’re looking for a more fixed, large-group tour, this might seem a bit pricier, but the added flexibility and personalized attention often outweigh the extra cost.
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Breaking Down the Experience: What to Expect

Pickup and Onset
Your day begins with a pickup from your accommodation or airport, which is a huge perk, saving you from navigating unfamiliar roads or taxis. Once you meet your driver-guide, they’ll ask about your interests and preferences to help craft your ideal day. If you’re coming with specific sites in mind, just let them know.
Exploring Santorini’s Iconic and Hidden Spots
The villages of Oia and Megalochori are among the most photogenic places on the island. Expect to wander narrow streets, be greeted by the sight of whitewashed buildings, and possibly catch some stunning views of the caldera. These locations are also perfect for taking those quintessential Santorini photos.
The black sand beaches of Kamari and Perissa are perfect for a quick break. The volcanic sand creates a striking contrast with the blue Aegean Sea, and you might even squeeze in some relaxation or a quick swim if the timing allows.
Scenic Viewpoints and Monastery
The Profitis Ilias Monastery at the highest point of the island offers sweeping views that are well worth the visit. It’s a great spot for photos and to learn about local religious history. The higher elevation also provides a refreshing breeze and a different perspective of the island’s volcanic landscape.
The Winery Visit
A stop at a local Greek winery offers more than just a tasting; it’s an authentic insight into Santorini’s agriculture and wine culture. The cellar tour allows you to see the traditional methods of wine production, all set against the backdrop of volcanic soil that imparts a unique flavor to the wines.
Flexibility and Customization
One of the biggest benefits is how much you can adapt the tour. Want to linger longer in Oia? How about skipping certain spots to explore a quaint village or scenic viewpoint? Your guide is there to facilitate your wishes as much as possible within the 5-hour window.
Who Would Love This Tour?

This private, customizable experience is especially ideal for travelers who are short on time but eager to see the highlights. It’s perfect if you prefer a relaxed, flexible schedule and enjoy having a local guide at your side. Couples, small groups, or solo travelers who want a curated experience without the hassle of large tour groups will find this appealing.
Keep in mind, it’s not suitable for those with mobility impairments, since some locations involve walking on uneven terrain. Families with older children who can handle some walking might enjoy it, but it’s primarily geared towards independent travelers or couples seeking a personalized day.
Final Thoughts

Choosing a private, tailor-made tour like this allows you to see Santorini on your own terms. The mix of iconic sites, scenic viewpoints, and local wine tasting makes for a well-rounded experience that can be adapted to your interests. The price is fair considering the personalized service, private transportation, and the chance to explore at your own pace.
If you’re someone who values flexibility, personalized attention, and authentic local experiences, this tour offers a flexible way to maximize your limited time on the island. You’ll come away with a handful of memorable sights, a few insider tips, and hopefully, some lovely photos to remember your trip.
All in all, it’s a good option for travelers who want to avoid cookie-cutter tours and prefer an experience that’s tailored just for them. Just remember to communicate your preferences beforehand, so your guide can help craft the best possible day.
5-h My Santorini Private Tailor Made Tour
FAQ

Is this tour suitable for large groups?
No, this is a private tour designed for small groups or individuals, providing a more personalized experience.
What is included in the price?
The cost covers pickup and drop-off from your accommodation or airport, a driver-guide, and a bottle of water. Wine tastings are included at the winery.
Can I customize the itinerary?
Absolutely. You can discuss your preferences with your guide, whether you want to focus on villages, beaches, viewpoints, or a mix of everything.
Does the tour operate year-round?
It begins at 09:15 a.m. from early April to early November, which covers the prime tourist season. Check availability for specific dates.
What should I bring?
Comfortable shoes, sunglasses, hat, sunscreen, and your ID or passport are recommended to enjoy the day comfortably.
Is it suitable for children?
The tour isn’t designed with mobility-impaired travelers in mind, but older children who can handle some walking may enjoy the flexible sightseeing.
How long does the tour last?
It’s a 5-hour experience, enough for a curated look at Santorini’s highlights without feeling rushed.
If you’re after a private, flexible way to experience Santorini’s beauty and charm, this tour from My Santorini Tour offers a personalized way to enjoy the best of what the island has to offer.
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