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304 North Cardinal St.
Dorchester Center, MA 02124

Experience Santorini's best wines on a private, guided tasting tour. Visit three wineries, sample 12-13 glasses, and enjoy stunning views in comfort.
Getting to know Santorini through its wines is one of those bucket-list experiences that really captures the island’s essence. This small-group wine tasting tour promises a relaxed, authentic adventure with visits to three distinguished wineries, tasting up to 13 glasses of wine, and learning about the island’s unique viticulture. Guided by a knowledgeable local, you’ll hop between charming vineyards in a sleek Mercedes minibus, making the journey as enjoyable as the wines themselves.
What we love most about this tour is how it balances informative tasting sessions with a personal touch—thanks to guides like Natalia and Mary, who go out of their way to make the experience memorable. The comfortable transportation and intimate size (max 12 travelers) create a friendly, relaxed atmosphere, perfect for both wine enthusiasts and casual tasters alike.
A potential consideration? If you’re hoping for a culinary experience with food, this tour doesn’t include eats, so plan to explore local tavernas afterwards to complement your wine journey. Still, the focus on wine education and authentic vineyard visits makes it ideal for those wanting to dive into Santorini’s wine culture without the crowds or commercial feel.
This experience suits travelers who appreciate authentic local experiences, enjoy learning about wine in a relaxed setting, and prefer small-group tours where you can ask questions and get personalized attention. It’s also perfect for those looking for a fun, educational afternoon—whether you’re a wine novice or a seasoned connoisseur.

If you’re someone who values authenticity and comfort, this wine tour hits the mark. From the moment the pickup begins—usually around 3:30 pm—you’re whisked away in a sleek, air-conditioned Mercedes minivan. The smaller group size means less waiting and more personal interaction with your guides, who are both friendly and well-versed in Santorini’s wine scene.
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Stop 1: Anhydrous Winery
Your first stop introduces you to the symbolic elements that influence Santorini wines—Volcano, Sun, Air, Water, Earth, plus Ash and Salt. The guide will explain how these natural factors shape the wines’ flavor profiles, making each sip an experience rooted in the island’s fiery landscape. Expect around 45 minutes here, giving you plenty of time to taste and ask questions. Reviewers have appreciated the insight—Kenya R shared, “Yoda made sure we enjoyed every minute,” highlighting how guides add value.
Stop 2: Estate Argyros
Established in 1903, Estate Argyros carries a deep legacy. The family’s focus has always been on quality grapes and meticulous vine cultivation. Here, you’ll learn how generations have refined their winemaking, with each vintage reflecting a blend of tradition and passion. The visit lasts about 45 minutes, and many reviews mention the warmth and knowledge of the hosts—Frennis C called the stop “awesome and welcoming.” You’ll get a real sense of the island’s dedication to excellence in wine.
Stop 3: Artemis Karamolegos Winery
This winery combines respect for Santorini’s heritage with innovative techniques, making it a standout. Artemis Karamolegos has received awards including recognition in both domestic and international circles. Expect another 45-minute stop filled with stories of how they invest in vineyards and winemaking technology. Reviewers like Christopher G pointed out how friendly and knowledgeable the staff are, making the experience both fun and educational.
The tastings are the core highlight; sampling 12-13 glasses of Greek wines gives you a well-rounded taste of what Santorini has to offer. Many guests, including Judy L, noted how meeting people like Mr. Argiros himself added a special touch. The quality of wines is consistently praised, with many reviewers mentioning the diversity and deliciousness of each glass.
The small group size fosters a relaxed atmosphere, encouraging conversations about wine, local culture, and the island’s landscape. The air-conditioned Mercedes minivan is a luxurious bonus, especially after spending a hot day outside. Plus, bottled water is provided, helping keep everyone refreshed.
At about $173.47 per person, this tour isn’t the cheapest option out there, but considering the all-inclusive tastings, private transport, and expert guides—it offers good value. The fact that the wines are included means no surprise expenses, and the intimate setting ensures you get personalized attention.
It’s also worth noting that bookings are typically made around 99 days in advance, which suggests it’s a popular choice for travelers wanting a quality experience without packing into a larger, more commercial tour.
While the tour doesn’t include food, many guests find the stopovers sufficient for a satisfying afternoon. However, it’s a good idea to plan for a light meal afterward to balance out the wine tastings. Dress smart casual to match the relaxed yet respectful vibe, and don’t forget your camera—scenic vineyard views and friendly guides make for great photos.
Weather can impact the experience, so if rain or high winds are forecasted, be prepared with an umbrella or raincoat. The tour confirms bookings upon receipt, and cancellations are free up to 24 hours before the start, offering peace of mind if your plans change.

This wine tasting experience is perfect for adventurous travelers eager to learn about Santorini’s wine culture in a relaxed, small-group setting. It’s ideal for those who value authenticity and personal touches—whether you’re a wine enthusiast or just curious about Greek wines. The knowledgeable guides, like Natalia and Mary, add a layer of richness that elevates the trip from mere tasting to a genuine cultural exchange.
If you enjoy comfortable transportation and intimate settings, you’ll feel at ease from start to finish. It’s also suitable for travelers who want a well-organized, predictable experience—no rushing, no crowds. Plus, the fact that it caters well to cruise ship guests, with pickup and drop-off included, makes it convenient for different travel plans.

How long does the tour last?
The tour runs for approximately 4 hours and 30 minutes, including transportation and visits to three wineries.
What’s included in the price?
You get hotel pickup and drop-off, transport by a comfortable Mercedes minivan, bottled water, and tastings of up to 13 glasses of wine.
Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours before the tour starts, which provides flexibility if your schedule shifts.
Is this tour suitable for everyone?
Most travelers can participate; the tour is designed to be accessible, with an emphasis on comfort and enjoyable learning.
Are food and additional drinks included?
No, food and extra drinks are not included in the tour fee. It’s recommended to have a light meal afterward if desired.
What kind of wines will I taste?
The tour focuses on local Santorini wines, which are influenced by volcanic soil and unique climate conditions, providing a distinctive flavor profile.
Is transportation provided?
Yes, pickup and drop-off from your hotel are included, making it convenient and stress-free.
What should I wear?
Smart casual attire is recommended. Comfortable shoes are advisable for walking at each winery.

This Discover Local Santorini Wine & Tasting tour offers a well-balanced, authentic introduction to the island’s wine scene. You’ll love the chance to visit three renowned wineries, taste a wonderful range of Greek wines, and learn from passionate guides—all in a cozy, small-group environment. The comfortable transportation and personalized attention make it an enjoyable way to spend an afternoon, especially if you’re looking for a more intimate experience away from the crowds.
While it’s on the pricier side, the value is clear when considering the quality of wines, expert guides, and seamless organization. If you’re a traveler who appreciates genuine cultural experiences and wants to take home not just photos but also a deeper appreciation for Santorini’s viticulture, this tour will serve you well.
Choose this experience if you’re seeking a blend of education, relaxation, and authentic Greek wine—an essential part of your Santorini adventure.