Private 5 Hours Highlights Tour by Native Guide with Wine Tasting

Exploring Santorini becomes a truly personal experience with the Private 5 Hours Highlights Tour by Native Guide with Wine Tasting. Priced at $231.68 per person, this tour offers a flexible, custom itinerary crafted with the help of a local guide. With an average booking time of 201 days in advance, it highlights some of the most iconic spots on the island, all while providing the comfort of door-to-door pickup and drop-off. The tour lasts approximately 4 hours 40 minutes to 5 hours, making it a manageable yet comprehensive way to see Santorini at your own pace. A standout feature is the wine tasting session at Argyros Estate, where you sample four different local wines. This private tour is particularly suited to those who appreciate personalized attention, flexibility, and a curated experience away from crowded group excursions.

While this tour suits most travelers, it’s ideal for those who value customization, local insights, and culinary experiences. The private nature ensures a relaxed atmosphere, and the inclusion of a wine tasting makes it perfect for enthusiasts or those looking to deepen their appreciation of Santorini’s wine culture. However, the tour does not include lunch or alcoholic beverages beyond the wine tasting, so plan accordingly if you desire a full meal during your day.

Key Points

• Private, customizable itinerary designed with a native guide
• Includes wine tasting at Argyros Estate, sampling four local wines
• Door-to-door pickup from hotels across Santorini, plus Fira cable car exit service
• Visit diverse stops: from the highest village Imerovigli to the lively Oia sunset spot
• Duration around 5 hours, with flexibility on pacing and stops

Exploring Santorini by Mercedes Minivan with a Local Guide

This tour departs with a private guide in a Mercedes minivan, ensuring a comfortable and intimate experience. The guide is available to help craft a personalized route, allowing travelers to focus on their interests—whether that’s beaches, villages, or scenic viewpoints. Unlike standard group tours, this experience emphasizes your own pace, with no rushing through highlights.

The door-to-door pickup covers accommodation across the island, including hotel or port transfers. For those arriving via cruise, Fira’s upper cable car station can also be arranged as a pickup or drop-off point. This level of convenience simplifies logistics and makes for a stress-free day of exploration.

Firostefani: The Crown of Fira

The tour kicks off in Firostefani, a village perched at the highest point of Fira. Known as the Crown of Fira, this spot offers sweeping views of the caldera and a sense of being close to the island’s heart. The visit lasts about 15 minutes, and it’s a perfect starting point to appreciate Santorini’s volcanic landscape. Since admission is free, it’s a quick stop that sets the tone for the scenic beauty ahead.

Imerovigli: Santorini’s Highest Town

Next, the guide leads you to Imerovigli, the highest town on the island. Here, you’re greeted by traditional white houses and iconic blue-domed churches. The village remains largely unchanged in style, reflecting its preservation as a traditional settlement. Today, Imerovigli is a hub for luxury hotels, restaurants, and shops, drawing visitors from around the world.

A 30-minute stop offers ample time to stroll, take photos of the vast plains and Aegean Sea views, or simply enjoy the peaceful atmosphere. This part of the tour balances scenic beauty with a touch of local culture, making it a highlight for many guests.

Oia: Famous for Sunsets and Charm

Oia is undoubtedly the most famous stop on this tour. Covering a small but vibrant part of the island, Oia is renowned for its breathtaking sunsets, but its sunrise is equally magical. Visitors can wander past pastel-colored houses, windmills, and dome-shaped churches. The town’s proximity to the caldera offers stunning views over the sea, perfect for photography or simply soaking in the scenery.

Spending about an hour in Oia allows enough time to explore its charming streets, visit boutique shops, or enjoy a coffee break. It’s a vibrant yet relaxed setting that captures the essence of Santorini’s allure.

Pyrgos Castle: A Step Back in Time

The tour continues to Castelli of Pyrgos, a medieval fortress built around 1580. As the highest settlement in Santorini, Pyrgos offers strategic views of the island’s plains and the Aegean Sea. The 30-minute stop provides an immersive experience in a traditional village environment, where the atmospheric castle stands as a reminder of the island’s history.

Walking through Pyrgos, visitors get a sense of local life preserved in its narrow streets and old stone buildings, adding a historical layer to the scenic journey.

Wine Tasting at Argyros Estate

One of the tour’s key highlights is the wine tasting session at Argyros Estate, located on the outskirts of Episkopi-Gonia. The modern winery features a spacious tasting room with panoramic ocean views, making the experience even more special. Over 45 minutes, you sample four different local wines, gaining insight into Santorini’s unique grape varieties and wine-making traditions.

This visit to the second-largest winery on the island offers a relaxing break with a chance to appreciate local flavors and learn from knowledgeable staff. The tasting is included in the tour price, adding significant value for wine enthusiasts.

Kamari Beach: Relaxation by the Volcanic Shore

The tour wraps up at Kamari Beach, known for its black volcanic shingle and lively atmosphere. Located in the southeast of Santorini, Kamari is bordered by dramatic cliffs and offers scenic views. The 20-minute stop allows visitors to walk along the beach, enjoy the gorgeous waters, or take photos against the striking backdrop.

While the black pebbles can be less comfortable than sand, bringing beach shoes helps. The quieter end of Kamari near the big rock is better suited for families and those seeking a more peaceful experience. The water quality is excellent once in, making it an ideal spot for a quick dip or seaside stroll.

Practical Details and Tour Inclusions

This private tour includes wine tasting, bottled water, and local driver/guide expertise. The vehicle is air-conditioned for comfort, and the tour features customized hotel, port, or airport pickup and drop-off. For cruise travelers, the Fira cable car exit is an available pickup point.

Not included are lunch and alcoholic beverages beyond the wine tasting. The tour is suitable for most travelers, with children over 18 and adults with mobility considerations able to participate comfortably. Confirmation is provided at booking, and free cancellation is available up to 24 hours before the scheduled start.

Guide Experience and Customer Feedback

Reviews highlight guides like Sofia, George, and Christo for their knowledge, friendliness, and personalized approach. The guides are praised for their ability to customize routes, making adjustments for medical or mobility needs, and for their photography skills. Guests appreciate the informative narration, flexible pacing, and personal touch that makes this tour stand out from larger group options.

Final Thoughts: The Value of a Private, Custom Santorini Tour

This private tour in Santorini offers a tailored experience focused on personalized stops and local insights. The wine tasting at Argyros Estate adds a unique flavor, while the flexibility in itinerary allows for exploring specific sights or spending more time at favorites. The door-to-door pickup and drop-off streamline logistics, and the small group setting ensures a relaxed atmosphere.

While it doesn’t include lunch or extensive physical activity, this tour suits those who want a comfortable, customizable day with a knowledgeable guide. It’s especially appealing for visitors who value culture, scenic beauty, and culinary experiences in Santorini.

Frequently Asked Questions

Is this tour suitable for children or individuals with mobility issues?
This tour is designed primarily for adults, with a minimum age of 18. Guides can adjust routes for mobility concerns, but the experience is best suited to those able to handle some walking.

Does the tour include lunch?
No, lunch is not included. The focus is on sightseeing and wine tasting, so travelers may want to plan for a meal separately.

What is the cancellation policy?
You can cancel up to 24 hours in advance for a full refund. Cancellations made less than 24 hours before the start are not refundable. Poor weather may lead to tour cancellations with a full refund or rescheduling.

How long does the wine tasting last?
The wine tasting session at Argyros Estate lasts approximately 45 minutes, with four wines sampled in a scenic setting.

What makes this tour special compared to other options?
The private, customizable approach and the inclusion of a local guide who can tailor the experience set this tour apart. The personalized stops and wine tasting add value that larger group tours often can’t match.

This private, flexible, and engaging tour offers a rich taste of Santorini’s sights, flavors, and local culture, making it an appealing choice for those seeking a tailored island adventure.