If you’re thinking about exploring Santorini and want a way to see the best spots without the hassle of navigating on your own, a private tour like the Best of Santorini Highlights Private 5 Hours Tour could be just what you need. It promises a personalized experience, with a guide dedicated to showing you the island’s top sights, from iconic villages to volcanic beaches.
What really catches our eye about this tour are two main things: the flexibility to customize your itinerary and the quality of the guides, who seem to make a real difference in the experience. Plus, the stops—ranging from Oia’s enchanting charm to the volcanic Red Beach—are truly some of the most photogenic spots you’ll find on the island.
That said, it’s worth considering that entrance fees for archaeological sites aren’t included, and if you’re eager to sample local wines, that’s an extra cost. Also, some reviews mention the hassle of transportation logistics, especially when it comes to things like cable car rides, so a bit of patience is helpful.
This tour appeals most to travelers who want a comprehensive, hassle-free overview of Santorini, especially if you prefer a private, personalized experience over group tours. It’s ideal for first-timers who want to hit the highlights with expert guidance, and those who appreciate the flexibility to tailor their day.
Key Points

- Private and customizable: You can adjust the itinerary to suit your interests.
- Expert guides: Knowledgeable locals make the experience engaging and informative.
- Convenience included: Pickup and drop-off at your hotel save time and effort.
- Balanced duration: Around five hours gives you a good taste of the island without feeling rushed.
- Cost value: At roughly $192 per person, it offers a rundown for the price.
- Additional costs: Entrance fees and wine tastings are extra, so plan accordingly.
Why Choose the Best of Santorini Highlights Tour?

This tour offers a true balance of structure and flexibility. You’ll be whisked between key sights while having the freedom to spend more time at the places that intrigue you most. It’s ideal if you’re new to the island or want to maximize your limited time, ensuring you hit the must-see highlights without the stress of planning every detail.
Being private means you won’t be in a large group, which can often lead to rushed stops or waiting around. Instead, your guide can tailor the pace. Many reviews emphasize how knowledgeable and friendly the guides are, making the experience more personable and interesting. For instance, one reviewer noted that their guide personalized the day for limited mobility, which shows how accommodating this tour can be.
Prefer personalized experiences? Here are other private options we've covered in Santorini
Exploring the Itinerary in Detail
Stop 1: Oia
We’d say this is the crown jewel of the tour. Oia’s charm is undeniable—whitewashed houses, narrow footpaths, and that famous blue-domed church make it a photographer’s paradise. It’s a place you’ll want to wander slowly, soaking in the atmosphere. Visitors often mention that Oia offers a peaceful, almost magical vibe. Expect at least an hour here, which gives ample time to explore the alleys, snap photos, and maybe grab a coffee or pastry with views of the caldera.
One reviewer called it “the unmatched beauty and tranquility,” which is a good way to describe it. Because it’s built on a slope, the views of the sea and sky are stunning from almost anywhere.
Stop 2: Firostefani
Just a short drive from Fira, Firostefani is often overlooked but offers breathtaking vistas. It’s known as the “crown of Fira,” perched on an elevated spot. The highlight here is the Blue Domed Church, which appears in countless photos of Santorini. With about 20 minutes allocated, you’ll have enough time to admire the views and take some selfies.
Stop 3: Profitis Ilias Monastery
Perched atop the island’s highest mountain (600m), this monastery, dating back to 1711, isn’t just a religious site—it’s also a viewpoint with panoramic vistas that are hard to beat. Just 30 minutes are scheduled, but that’s enough to soak in the scenery and appreciate the historical significance. Expect spectacular views beyond description, making it a must-see for landscape lovers.
- Half-Day Exclusive Catamaran Cruise in Santorini with Meal and Open Bar
- Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers
- Half Day Premium Catamaran Cruise in Santorini including Oia
- Luxury Small-Group Catamaran Cruise with BBQ, Open bar & Transfer
- Santorini Private Custom Tours 4 – 7 Hours
- Traditional Greek Night live Music & Dinner Show in Santorini
Stop 4: Megalochori Village
This authentic, 17th-century village is everything a traditional Greek village should be—warm, inviting, and full of charm. Wander through narrow streets lined with old mansions, courtyards, and traditional architecture. It’s a less touristy spot, perfect for those wanting a feel for local life. Reviews repeatedly praise the picturesque nature of Megalochori, with one calling it “the big village that’s full of history and character.”
Stop 5: Perissa Black Sand Beach
After some cultural sightseeing, it’s time to relax. Perissa’s black sand beach is famous for its volcanic sand and clear waters. It’s a lively spot, often busy, but perfect for a quick dip or just lounging. Many visitors enjoy grabbing a bite at seaside tavernas, sampling local specialties while gazing at the sea. About 20 minutes are set aside here, which seems enough for a quick view and a snack.
Stop 6: Red Beach
The dramatic Red Beach is arguably the most iconic spot on this tour. Its striking red volcanic rocks contrast sharply with the blue of the sea—a sight that truly stays with you. Spending around 30 minutes here allows for photos, a walk along the shore, and appreciating the unusual landscape. This is one of those “must-see” sights, often praised for its scenery and uniqueness.
Stop 7: Venetsanos Winery
Ending your tour at a winery adds a delightful touch. Santorini is renowned for its wines, and Venetsanos Winery offers a chance to taste some of the island’s unique varieties. The hour-long stop is an excellent way to unwind, learn about local wine-making traditions, and sample some wines—though, of course, tastings are extra. Multiple reviews highlight that the winery visit is one of the highlights, with the opportunity to indulge in local flavors.
What to Expect During the Tour

Travel is in a comfortable, air-conditioned minivan, which makes moving between these diverse spots easy and enjoyable. The tour’s flexible nature means your guide can adapt the schedule based on your interests or time constraints. Many reviews appreciate the guides’ knowledge and friendliness, making the experience more engaging than a standard sightseeing bus.
Pickup and drop-off are included, so you won’t have to worry about logistics or finding your way to meeting points. The tour is designed to be around five hours, a good chunk of time to see multiple sights without feeling hurried.
It’s worth noting that entrance fees for sites like archaeological sites aren’t included, so if you’re keen to explore ruins or other historical sites, budget for those additional costs. Wine tastings are also extra, but you’ll get a chance to taste some fantastic local varieties if you choose to visit the winery.
Accessibility & Suitability
While most travelers can participate, keep in mind that Santorini’s terrain can involve some walking on cobblestones and hill climbs. One reviewer mentioned that the guide was able to personalize the experience for limited mobility, which is encouraging if you have some restrictions. Children are welcome but should be accompanied by an adult.
Price & Value
At around $192 per person, this tour offers good value considering it’s private and includes hotel pickup/drop-off. The variety of sights, combined with expert guides and the ability to customize, makes it a worthwhile investment for those wanting a rundown without the stress of planning every detail.
Who Is This Tour Best For?

This private tour fits travelers who value personalized attention and want to see multiple highlights in a relaxed manner. It’s perfect for first-time visitors who prefer a curated experience or anyone who wants a hassle-free day with the flexibility to focus on what interests them most. If you’re traveling with a partner, friends, or even a small family, it offers both intimacy and convenience.
Those who appreciate good local wines will find the winery stop particularly appealing, especially if you like tasting and learning about regional specialties.
If you’re after an in-depth exploration, flexibility, and expert guidance, this tour ticks all those boxes. On the flip side, if you’re on a tight budget or prefer independent travel, you might find this a bit pricier than self-guided options, especially with additional fees.
Best of Santorini Highlights Private 5 Hours Tour
“The tour was absolutely amazing. Best way to see some of the best spots in Santorini. Our tour guide was knowledgeable and friendly. He made sure w…”
FAQ

Is transportation included in the tour? Yes, all transport is provided in an air-conditioned minivan, making it easy to move between stops comfortably.
Can I choose my departure time? Yes, there are multiple departure times available, so you can pick a slot that fits your schedule.
Are entrance fees for sites included? No, entrance fees for archaeological sites aren’t included, so plan for those extra costs if you want to visit specific sites.
Does the tour include wine tastings? Wine tastings at Venetsanos Winery are not included in the price, but you can opt to sample local varieties during your visit.
Is this tour suitable for children? Children are welcome, but they must be accompanied by an adult. Keep in mind the walking involved and terrain.
How long is the tour? The tour lasts about five hours, including all stops and transportation time.
What if I need special accommodations? The tour is flexible, and guides can personalize the experience for limited mobility—just mention your needs when booking.
In summary, the Best of Santorini Highlights Private 5 Hours Tour is a well-rounded, flexible way to explore the island’s top sights with expert guides and personalized service. It’s especially suited to those who want to avoid the chaos of large groups and enjoy a tailored experience that hits all the main spots while offering a touch of local flavor—like wine tasting and authentic villages. If you’re after a memorable, convenient day on Santorini, this tour could very well be your best bet.
More Private Tours in Santorini
More Tours in Santorini
More Tour Reviews in Santorini
More Santorini experiences we've covered
- Flying Dress Photoshoot Experience in Santorini
- Santorini Oia: Private Sunset Catamaran Cruise with BBQ & Drinks
- Private Full-Day Santorini Hidden Gems and Wine Experience
- Santorini Waves of Passion
- 5 Hours Boat Rental in Santorini
- Santorini Summer Panorama
- Santorini Taxi / Transfer Service From or To Airport
- Kayak Rental Adventure in Watersports Santorini
- Santorini: Private Sailing Yacht Cruise with Meal & Drinks
- Santorini Private Highlights Tour
- Best of Santorini Highlights Private 5 Hours Tour
- Santorini Group Transfers: 24/7 We are at your service


