Santorini: Guided Highlights Tour with Private Wine Tasting

If you’re planning a trip to the iconic island of Santorini, this private 6-hour highlights tour offers a balanced mix of stunning scenery, cultural spots, and a taste of local wine. Priced at $305 per person, it’s an investment in a personalized experience that takes you beyond the typical cruise ship stops, with visits to Oia, the Red and Black beaches, Megalochori, and the Prophet Elias Monastery. The tour culminates in a family-run winery where you can sample four varieties of Santorini’s famous wine.

What we love most about this tour is its flexibility and the chance to experience remote villages and less touristy spots alongside the must-see sights. The intimate setting means you’ll get more tailored attention from your guide, and the small group size makes it easier to ask questions and enjoy the moment. Also, the wine tasting at a 300-year-old winery adds a delicious and authentic touch that’s hard to beat.

A possible consideration is that this tour might not suit travelers with mobility issues, given the walking involved and the nature of some stops. Plus, if you’re hoping for a gourmet lunch or museum entries, you’ll need to organize those separately, as they’re not included. Still, for first-time visitors who want to see the highlights comfortably and authentically, this tour fits the bill perfectly.

This experience is best suited for first-time visitors to Santorini, cruise ship passengers looking for a comprehensive taste of the island, and anyone who appreciates a personalized, relaxed pace combined with cultural insight and good local wine.

Key Points

Personalized Experience: Private group with a flexible itinerary tailored to your interests.
Highlights Included: Oia, Red & Black beaches, Megalochori, Prophet Elias Monastery.
Authentic Wine Tasting: Sampling four local wines at a 300-year-old family winery.
Stunning Views & Remote Villages: Enjoy panoramic vistas and less touristy areas.
Comfort & Convenience: Hotel/port pickup and drop-off in a luxury A/C minibus.
Ideal for First-Timers: Great introduction to Santorini’s top sights and flavors.

You can check availability for your dates here:

A Closer Look at the Tour Itinerary and Experience

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Starting Point: Comfort and Convenience

Your day begins with a pickup from your hotel or the nearest accessible location. This door-to-door service simplifies logistics, especially for those unfamiliar with the island. The guide, who speaks fluent English (and Spanish if needed), will be your storyteller and navigator, making sure that your experience flows smoothly. Expect to be transported in a luxury air-conditioned minibus, ensuring comfort amid the Santorini heat or wind.

Oia: The Picture-Perfect Village

First stop: Oia, the crown jewel of Santorini, famous for its blue-domed churches and spectacular panoramic views of the caldera. We loved the way the guide helped us navigate the narrow streets, which are often crowded with photographers and souvenir shops. While Oia is popular, visiting early or later in the day can help avoid the crowds, making for a better photo op. You’ll have time to enjoy the charming atmosphere, snap photos of the iconic scenery, and soak in the atmosphere of this postcard-perfect village.

Megalochori: Authentic Village Life

Next, we drive through the rocky hills and sparse grassland to reach Megalochori, a quieter village far less commercialized than Fira or Oia. Walking along winding paths and admiring the tiered bell towers, we felt transported to a different pace of life. The guide offers intriguing insights into local architecture and traditions, making this stop more than just a photo opportunity. We appreciated how this visit gave us a genuine taste of village life away from the crowds.

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Family-Run Winery: A Tasting to Remember

The highlight for many travelers is the visit to a 300-year-old family-run winery. Here, you’ll sample four different local wines, accompanied by some cheese and rusks. The guide explained the unique volcanic soil and climate that give Santorini wines their distinctive character. Our fellow travelers found this tasting especially memorable—one said, “the wines were fantastic, and the setting was charming.” This authentic experience allows you to connect with the island’s wine-making tradition, which dates back centuries. It’s an excellent value for those interested in food and drink, offering a taste that you can’t find in stores or typical tourist spots.

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Red and Black Beaches: The Geological Marvels

After the wine, you’ll visit Red Beach, a natural wonder with reddish cliffs formed by volcanic activity. The striking geology makes it one of the most photogenic spots on the island. We loved the way the guide helped us find safe spots to take pictures and explained the volcanic history behind the cliffs.

Then, a short drive takes you to Perivolos Beach, known for its black volcanic sand. Relaxing here, you can dip your toes in the water or just enjoy the view. This beach is perfect for those seeking a quick break from sightseeing and a chance to experience Santorini’s volcanic landscape firsthand.

Prophet Elias Monastery: Panoramic Views from the Highest Point

The tour culminates at the Prophet Elias Monastery, perched 565 meters above sea level. Standing here, we experienced a sense of peace and enjoyed sweeping views of the entire island. The monastery’s serene atmosphere offers a moment of quiet reflection and a chance to capture stunning photos of Santorini’s rugged terrain and blue waters.

Wrapping Up and Return

After our scenic explorations, the guide drops us back at our starting point or hotel, ending a well-paced, enriching day. The private nature of the tour means we could customize the experience slightly—whether lingering longer at a favorite spot or skipping a less-interesting stop.

What Makes This Tour Valuable?

This tour’s value lies in its personalized approach and the variety of sights covered within a manageable timeframe. The small group size ensures your guide can offer insights tailored to your interests and answer questions without feeling rushed. The inclusion of local wine tasting adds an authentic flavor, quite literally, to your Santorini experience.

The transportation aspect is smooth, with hotel or port pick-up, so you don’t waste precious time figuring out logistics. The stops are well-chosen—covering both famous landmarks and hidden gems—making this an excellent introduction for first-time visitors or cruise ship passengers short on time.

The Tour’s Strengths

Flexibility and personal attention from a knowledgeable guide
Authentic wine tasting at a family-run, historic winery
Access to remote villages and less touristy spots
Stunning vistas from elevated points like Prophet Elias Monastery
Comfortable transportation that simplifies the day

Possible Drawbacks

Not suitable for travelers with mobility challenges
Lacks a dedicated lunch or museum visits (these can be arranged separately)
Short time at each stop, so some details might be missed if you prefer longer explorations

Who Should Consider This Tour?

If you’re visiting Santorini for the first time and want a structured yet flexible overview of the island’s most photogenic and culturally interesting sites, this tour is a solid choice. It’s especially good for cruise passengers or those short on time but eager to see both the famous and lesser-known parts of Santorini. Wine lovers and those seeking an authentic, local experience will appreciate the winery visit.

Travelers who prefer a relaxed pace with a focus on personalized service will find this tour more satisfying than larger group excursions. Keep in mind, it’s not ideal if you have limited mobility or want a full, museum-heavy experience.

FAQs

How long is the tour?
The tour lasts approximately 6 hours, including pick-up and drop-off.

What’s included in the price?
You get hotel/port pickup and drop-off, transportation in a luxury A/C minibus, an English-speaking guide, a visit to a family-run winery with wine tasting and cheese, bottled water, and all taxes.

Are there any additional costs?
Yes, cable car tickets for cruise ship travelers cost around 6 euros per person, per way. Optional museum entrance fees and meals are not included.

Can I customize the stops?
The tour is private and flexible, so you can discuss preferences with your guide beforehand or during the trip.

Is this tour suitable for children or pregnant women?
It’s not recommended for pregnant women or those with mobility issues due to walking and some uneven surfaces.

What should I bring?
Bring a passport or ID card, sun protection, comfortable shoes, and a camera.

How do I get to the meeting point if I’m not staying at a hotel?
The guide will send details of the meeting location at least one day before if your hotel isn’t accessible.

Can I book this last minute?
Availability varies, so check in advance. You can reserve now and pay later, offering flexibility.

Is the wine tasting suitable for all ages?
The tasting is designed for adults; minors are not permitted to participate in wine tasting.

What’s the best time of day to take the tour?
Check availability for starting times; mornings or late afternoons typically help avoid crowds at popular sights like Oia.

For travelers seeking a comprehensive, authentic taste of Santorini without the hassle of planning every detail, this private highlights tour offers a perfect blend of culture, scenery, and local flavor. The focus on personalized service and small-group intimacy ensures that you’ll have room for questions, spontaneous stops, and genuine moments away from the crowds.

The inclusion of a historic winery adds a unique dimension, making this more than just a sightseeing trip; it’s an immersion into the island’s soul. Whether you’re a first-time visitor eager to see the top sights or a traveler wanting a relaxed day with meaningful stops, this tour delivers a well-rounded Santorini experience.

If you’re after a value-packed, authentic introduction to Santorini’s most photogenic spots and flavors, this private tour is well worth considering. Just remember—bring your camera, a sense of curiosity, and an appetite for excellent wine and scenic views.