Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Discover Santorini's highlights on this private 4.5-hour tour, featuring iconic sites, stunning vistas, and expert-guided wine tasting for an authentic experience.
Experience the beauty of Santorini with the Half Day Santorini Highlights Private Tour offered by Touring with Kostas. Priced at $348.32 per person, this 4-hour 30-minute adventure provides a personalized journey through some of the island’s most captivating sights. With a 5.0/5 rating based on 50 reviews, and 98% recommending the tour, it’s clear that guests find it both memorable and well worth the experience. The tour starts from the cable car station in Fira and is operated with a private vehicle, making it ideal for those seeking comfort and flexibility.
This tour is particularly suited for visitors who want a comprehensive yet relaxed overview of Santorini’s highlights, guided by a knowledgeable local. It includes visits to picturesque villages, a historic monastery, and a top-notch wine tasting, all within a half-day window. While it’s accessible to people with moderate physical fitness and fully private, guests should be aware that some walking and stairs might be involved at certain stops.


The tour begins promptly at the cable car station in Fira, with guests meeting a guide named Kostas who holds a sign with their name. This convenient meeting point is close to public transportation, making it easy to access from most accommodations. After greeting, guests board an air-conditioned minivan or private vehicle for the journey ahead.
Kostas leads the group through the island, sharing insights about Santorini’s history, geology, and culture. The private setting ensures personalized attention, allowing for questions and tailored pacing. The tour’s design accommodates moderate physical fitness levels, but those with mobility concerns should note some walking and steps at stops.
Prefer personalized experiences? Here are other private options we've covered in Santorini

One of the highlights of this tour is a visit to Oia, famous for its whitewashed buildings, blue-domed churches, and stunning sea views. Kostas guides visitors through the village’s shops and cafes, emphasizing the calm and laid-back atmosphere. Guests have ample time to browse local crafts and capture photos of the iconic scenery.
The calm vibes of Oia provide a perfect setting for relaxing strolls and picture-perfect moments. The guide ensures that visitors see the most scenic spots, avoiding crowded areas and offering prime viewpoints. This stop offers a chance to experience authentic Santorinian charm, away from more tourist-heavy areas.
A key feature of this private tour is a visit to the highest point on the island, where an ancient monastery stands. From this vantage point, visitors enjoy sweeping views of the sky and the expanse of the ocean. The site’s historical significance, combined with its breathtaking scenery, makes it a favorite for photo opportunities and quiet reflection.
Kostas shares stories about the monastery’s history and its role in Santorini’s past. The level of accessibility at this stop is accommodating, but some walking and standing are involved. The location provides an ideal spot for panoramic photos and appreciating the island’s volcanic landscape.

For those on the afternoon tour, the timing aligns perfectly with sunset, adding a magical glow to the wine tasting experience. Kostas is familiar with the best cellar doors on the island, guiding the group to a local vineyard renowned for its quality wines.
Guests enjoy sampling a variety of local wines, often paired with traditional snacks. The wine tasting is hosted at a carefully chosen cellar, where the guide’s knowledge enhances the experience. This feature allows visitors to savor authentic Santorinian wines in a relaxing setting, making it a true highlight of the tour.

Avoid the hassle of public transport or taxis, as the entire tour is operated with private vehicles. This not only saves time but also offers a more comfortable and flexible way to explore the island at your own pace. The air-conditioned minivan ensures a pleasant journey, especially during warmer months.
Kostas manages the pacing carefully, ensuring guests spend enough time at each stop without feeling rushed. The private nature of the tour means that it can be customized to suit individual preferences or physical needs, as some stops can be modified if necessary.

Accessibility is a key feature of this experience. The tour welcomes guests with disabilities and wheelchairs, making it inclusive for a broad range of visitors. Kostas and the vehicle are equipped to handle those with mobility challenges, ensuring everyone can enjoy the sights comfortably.
Guests with specific needs can expect personalized assistance and flexible timing, especially at locations where some walking or stairs might be involved. This commitment to accessibility is a major plus for travelers seeking an accommodating and enjoyable experience.

Kostas is frequently praised for his knowledge, storytelling, and friendly demeanor. Reviews highlight how he adapts the tour to individual interests and pace, making the experience both informative and fun.
He shares stories, local insights, and historical context that bring the sights to life. Guests often appreciate how he modifies the route for those with mobility issues or specific preferences, ensuring everyone has a memorable day. His engaging personality and deep familiarity with the island make him a standout guide.

With a duration of approximately 4 hours 30 minutes, this tour balances sightseeing and relaxation perfectly. The itinerary hits the key highlights without feeling rushed, giving ample time to explore each location.
Starting at the top of the cable car and ending back at the same point, the tour maintains a smooth flow. Guests should be prepared for some walking and standing, but the pace is moderated to suit most, with the option for tailored modifications.
At $348.32 per person, the tour offers a comprehensive and personalized way to see Santorini’s most renowned sights in just half a day. The inclusion of a private guide, luxury transportation, and a wine tasting experience add significant value.
Reviews consistently praise the knowledgeable guide and the quality of the sights, making this tour a worthwhile investment for visitors who want a curated experience without the crowds or the chaos of self-guided exploration.
This private tour is perfect for couples, families, or small groups seeking a relaxed, informative, and flexible way to experience Santorini. The personalized guidance and accessible features make it especially suitable for international visitors, older guests, or those with mobility concerns.
Guests looking for scenic views, historical insights, and authentic wine tasting will find this experience delivers on all fronts. The 4.5-hour timeframe is ideal for travelers with limited time but wanting a meaningful taste of the island.
The Half Day Santorini Highlights Private Tour offers a well-rounded, personalized exploration of the island’s most iconic sites, with a friendly and knowledgeable guide named Kostas. The private transportation and full accessibility ensure a comfortable journey, while the timed wine tasting adds a special local flavor.
While the tour is priced at $348.32 per person, it is highly rated for its quality, flexibility, and guide expertise. It suits those who value tailored experiences and want an intimate look at Santorini’s beauty and history in just a few hours.
This tour is a great choice for visitors who appreciate detailed storytelling, stunning vistas, and authentic wine experiences — all delivered in a relaxed, private setting.
“Kostas was a fantastic guide! He is very knowledgeable, entertaining and made the day fun for the adults and the Kids in our group. Would Highly re…”
Is this tour suitable for people with mobility issues?
Yes, the tour is fully accessible for guests with disabilities and wheelchairs, with modifications available to accommodate walking or steps.
What is included in the tour price?
The price covers the professional guide, private transportation in air-conditioned vehicles, and the wine tasting at a local cellar. Alcoholic drinks are available for purchase separately.
Where does the tour start and end?
The tour begins at the cable car station in Fira, and ends back at the same meeting point after approximately 4.5 hours.
Can I customize this tour?
Yes, the tour is private and flexible, allowing the guide to modify stops or pacing according to guest preferences and needs.
How long is the wine tasting?
The wine tasting occurs at the top cellar, typically coinciding with sunset if the afternoon option is chosen, lasting enough for guests to sample a variety of local wines.
What is the typical duration of the tour?
The tour lasts around 4 hours 30 minutes, providing a full yet relaxed sightseeing experience.
Is this tour recommended by many travelers?
Absolutely, with a 5.0/5 rating from 50 reviews and 98% recommending it, this tour is highly praised for guide expertise and overall experience.
What makes this tour stand out from others?
The personal attention of a knowledgeable local guide like Kostas, combined with carefully selected stops and accessible features, makes this tour especially appealing for those seeking a genuine and comfortable exploration of Santorini.