Santorini Highlights and Venetian Castles Small-Group Day Tour - Akrotiri and the View of the Caldera

Santorini Highlights and Venetian Castles Small-Group Day Tour

Discover Santorini's top sights on a small-group full-day tour, including Venetian castles, black beaches, wine tasting, and a stunning sunset in Oia.

Exploring Santorini in a single day might seem ambitious, but the Santorini Highlights and Venetian Castles Small-Group Day Tour makes it possible. Priced at $104.27 per person, this 10 to 11-hour adventure offers a well-rounded experience, from Venetian castles to black sand beaches and spectacular sunset views in Oia. The tour departs with hotel pickup in the late morning, making it convenient for travelers who prefer a relaxed start. Its small-group format, with a maximum of 18 participants, ensures a more personalized and engaging experience.

What sets this tour apart is the combination of historical sites, local wine tasting, and scenic stops all in one day. The guide’s reputation for being knowledgeable and engaging is echoed in reviews, highlighting how the tour makes the island’s history come alive. While the tour skips the Symposion music workshop from October to March, it still offers a rich itinerary for those eager to see Santorini’s key sights without the hassle of planning each stop individually.

Key Points

Santorini Highlights and Venetian Castles Small-Group Day Tour - Key Points

  • Small-group tour with a maximum of 18 people for a more intimate experience
  • Includes hotel pickup and drop-off across most of the island
  • Visit iconic Venetian castles in Pyrgos and Emporio
  • Enjoy wine tasting at the Artemis Karamolegos Winery
  • Relax on Perissa’s black sand beach for two hours of free time
  • Witness the stunning sunset in Oia from the Venetian castle
  • Tour duration is approximately 10 to 11 hours, starting at 10:30 am
  • Admission costs for stops like Symposion are not included, except for wine tasting

The Tour Starts with the Hilltop Village of Pyrgos

Santorini Highlights and Venetian Castles Small-Group Day Tour - The Tour Starts with the Hilltop Village of Pyrgos

The journey begins at Castelli of Pyrgos, a village built on a hilltop with an impressive Venetian castle overlooking the caldera. This location offers panoramic views of the island’s volcanic landscape. Visitors walk to the top, taking in the historic architecture and scenic vistas that make Pyrgos a highlight. This stop is free of charge and lasts about an hour. It’s an ideal introduction to Santorini’s architectural charm and strategic fortress locations.

Exploring the Traditional Village of Megalochori and Music Workshop

After Pyrgos, the tour heads to Megalochori, where guests can visit the Symposion—a workshop of traditional Greek music instruments. This stop is full of information about Greek mythology and music. The interactive presentation offers a glimpse into Greek cultural traditions. However, from October 15 to March, the tour skips this stop, so travelers should plan accordingly. The visit lasts about an hour, though admission to the Symposion costs €13 per person.

Akrotiri and the View of the Caldera

Santorini Highlights and Venetian Castles Small-Group Day Tour - Akrotiri and the View of the Caldera

Next, the group drives around the Akrotiri area, where a short photo stop provides views of the castle of Akrotiri and the caldera from the south side of the island. This free stop lasts about 30 minutes and offers photo opportunities of the volcanic landscape and surrounding cliffs. It’s a chance to appreciate Santorini’s geology and volcanic history.

Relaxing on Perissa Black Sand Beach

Santorini Highlights and Venetian Castles Small-Group Day Tour - Relaxing on Perissa Black Sand Beach

After the scenic drive, free time is allocated for relaxation at Perissa’s black sand beach. This famous volcanic beach invites visitors to swim, sunbathe, or grab lunch at nearby tavernas. The two-hour window lets guests unwind and enjoy local flavors. The beach is free to access, making it a much-appreciated break from the sightseeing.

Discovering Emporio’s Venetian Castle

Santorini Highlights and Venetian Castles Small-Group Day Tour - Discovering Emporio’s Venetian Castle

Following the beach break, the tour visits Emporio, a quaint village with small streets and a well-preserved Venetian castle. Travelers walk through the medieval trade center, gaining insights into Santorini’s historical significance. This one-hour stop is free and offers a chance to explore authentic local architecture and old town charm.

Wine Tasting at Artemis Karamolegos Winery

Santorini Highlights and Venetian Castles Small-Group Day Tour - Wine Tasting at Artemis Karamolegos Winery

One of the tour’s highlights is a wine tasting at Artemis Karamolegos Winery, housed in an old canava. In about 45 minutes, visitors sample local wines, learning about Santorini’s unique viticulture. The admission fee is included, and reviews praise the quality of the wines and the welcoming atmosphere. It’s a perfect way to appreciate the local flavors and regional craftsmanship.

Firostefani’s Iconic Blue Dome and Skaros Rock

Santorini Highlights and Venetian Castles Small-Group Day Tour - Firostefani’s Iconic Blue Dome and Skaros Rock

The tour makes a brief stop in Firostefani to capture pictures of the Blue Dome and Skaros Rock. This 20-minute visit offers breathtaking views of the caldera and the former capital of the island during the Venetian era. It’s an ideal spot for photo enthusiasts and those wanting a quick, stunning view of Santorini’s architecture.

Sunset in Oia from the Venetian Castle

Santorini Highlights and Venetian Castles Small-Group Day Tour - Sunset in Oia from the Venetian Castle

The final stop is in Oia, famous for its narrow streets, cave houses, and romantic chapels. The tour concludes with the spectacular sunset viewed from the Venetian castle, an iconic image of Santorini. Guests have about two hours here to explore the picturesque village, shop, or dine. After sunset, a comfortable transfer takes everyone back to their hotels.

Practical Logistics and Group Size

This small-group tour limits participants to 18, ensuring a personalized experience. The air-conditioned minivan transports guests comfortably between stops. Hotel pickup begins in the late morning, around 10:30 am, providing a relaxed start. The tour lasts about 10 to 11 hours, making it a comprehensive way to see Santorini without feeling rushed.

The Guide’s Role and Local Insights

Throughout the day, the tour guide is praised for their knowledgeable and engaging style, making complex history accessible and interesting. Reviews highlight how guides like Gregory and George bring the sites to life with stories and local context. Their safe driving and pace management ensure a smooth experience, especially given the moderate physical activity involved.

Value for Money and Tour Inclusions

Priced at $104.27, this tour offers excellent value considering the full day of sightseeing, wine tasting, and hotel transfers. The small-group format enhances the experience, avoiding the crowds often associated with larger tours. While food and additional drinks are not included, the lunch break at Perissa and the wine tasting compensate well for the price.

Who Will Appreciate This Tour Most?

This comprehensive tour suits visitors who want to see many of Santorini’s highlights in a single day. It’s ideal for those who prefer guided exploration with transportation included, especially if they want to learn about the island’s history, sample regional wines, and capture stunning photos. The moderate physical demands mean it’s suitable for most guests, but some walking and climbing are involved.

Santorini Highlights and Venetian Castles Small-Group Day Tour: Final Thoughts

This tour delivers a well-balanced mix of history, scenery, and local flavors, all within a comfortable small-group setting. The expert guides elevate the experience with their knowledge and storytelling, making each stop more meaningful. The visit to Venetian castles, black beaches, and sunset in Oia are particular highlights.

While it doesn’t include all stops during off-season or paid entrance fees for some attractions, the overall value and convenience are hard to beat. This tour is especially suited for first-time visitors eager to maximize their day in Santorini without the stress of planning every detail. Its personalized approach and scenic stops make it a recommended choice for those wanting a thorough and enjoyable island overview.

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Santorini Highlights and Venetian Castles Small-Group Day Tour



5.0

(390 reviews)

91% 5-star

“Very knowledgeable and easy to listen to guide. A comprehensive, fascinating tour of Santorini. Highlight was the Symposium and wine tasting.”

— Annica G, May 2025

Frequently Asked Questions

Is hotel pickup available for this tour?
Yes, hotel pickup and drop-off are included across most of the island.

How long does the tour last?
The tour duration is approximately 10 to 11 hours, starting at 10:30 am.

What stops are included in the tour?
Stops include Pyrgos, Megalochori, Akrotiri, Perissa beach, Emporio, wine tasting at Artemis Karamolegos, Firostefani, and Oia.

Is food included in the tour?
No, lunch and drinks are not included, but there are plenty of options during free time at Perissa.

Are entrance fees included?
Entrance to Symposion is not included (costs €13), and some stops are free of charge.

Can children attend this tour?
Children under 7 years old cannot attend the Symposion music presentation, but the rest of the tour is suitable for most ages.

What is the group size limit?
The tour maximum is 18 participants, ensuring a more personal experience.

Is this tour suitable for those with limited physical fitness?
Yes, but moderate walking and climbing are involved, so some physical effort is expected.

What is the price of this tour?
The cost is $104.27 per person, offering good value for a full-day guided experience.

How do I reserve a spot?
Bookings should be made in advance, as the tour is often booked 52 days ahead.