If you’re planning a trip to Santorini and want to combine the island’s stunning scenery with some excellent wine tasting, the Winery – Oia Sunset Tour might catch your eye. This roughly five-hour experience takes you through two distinct wineries, offers a peek into local winemaking traditions, and ends with that iconic sunset in Oia. It’s a popular choice, often booked around two months in advance, and aimed at adults who enjoy good wine and scenery.
What we like about this tour is its intimate vibe – capped at just 15 travelers, so it feels less like a crowd and more like a personalized experience. The chance to sip wine while soaking in caldera views, combined with a sunset in one of Greece’s most photographed villages, makes it feel special. Plus, the guide’s insights about winemaking add a layer of depth many casual tastings lack.
A consideration to keep in mind is the weather. As some reviews have pointed out, rain can change the experience, limiting your visit to Oia and the sunset. Also, the food offerings are fairly minimal, so if you’re expecting a full meal, you might be disappointed. But if you’re after a relaxed, scenic, wine-focused outing, this tour could suit you well.
This experience would be ideal for wine lovers, sunset seekers, and those who prefer small-group settings for a more relaxed vibe. It’s not perfect for families or anyone looking for a full-day tour with a lot of food or activity, but if intimacy and scenery top your list, it’s worth considering.
- Key Points
- Exploring the Itinerary in Detail
- Start at Venetsanos Winery
- Visit to the Santorini Wine Museum
- Sunset at Oia’s Sun Spirit Cocktail Bar
- What’s Included and What’s Not
- Weather and Timing Considerations
- Authentic Feedback From Travelers
- The Sum Up
- Winery – Oia Sunset Tour
- FAQ
- More Wine Tours in Santorini
- More Tours in Santorini
- More Tour Reviews in Santorini
- More Santorini experiences we've covered
Key Points

- Intimate Group Size: Just 15 travelers or fewer, making it feel personal and less rushed.
- Stunning Views & Sunset: The combination of caldera vistas and the sunset in Oia is a highlight.
- Diverse Wine Tastings: Sampling around 8 wines across two different wineries offers good variety.
- Educational Value: You’ll learn about winemaking from knowledgeable guides and at the wine museum.
- Good Value for Money: For $127.45, this includes visits, tastings, transportation, and sunset viewing.
- Weather-Dependent: Rain can impact the experience, especially the sunset and Oia visit.
Exploring the Itinerary in Detail

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Start at Venetsanos Winery
The journey begins at Venetsanos Winery, probably the most visually striking stop. Located in a breathtaking spot overlooking the caldera, it’s renowned for its unconventional architecture—constructed from above and sliding downward—adding a touch of visual intrigue. Here, you get to taste three of their notable wines while appreciating panoramic views that make the experience feel almost surreal.
Guests often find this part memorable, especially because of the spectacular views and the chance to learn about the winery’s unique design and winemaking process. As one reviewer put it, “Good wine and informative,” which is a solid endorsement for those wanting a blend of education and scenic beauty.
Visit to the Santorini Wine Museum
The tour then takes you to a traditional, family-owned winery in the heart of the island. This spot offers an authentic look at how winemaking has been part of local life for generations. Here, you’ll sample four more wines, including volcanic white wines and the island’s famed desert wine.
Walking through the wine museum, you get a sense of the blending of ancient traditions with modern techniques. This stop is especially valued by those interested in the island’s history and culture, and it’s a chance to try some of Santorini’s most distinctive wines. One guest shared, “Interesting to walk through the wine museum,” highlighting how this part of the tour adds depth.
Sunset at Oia’s Sun Spirit Cocktail Bar
The final stop is in the picture-perfect village of Oia, renowned for its sunset views. The Sun Spirit Cocktail Bar offers a prime position to sip your last wine while watching the sun dip into the Aegean Sea. It’s a quintessential Santorini moment, and many find it to be the perfect way to conclude the tour.
However, weather can be unpredictable, and a few guests noted that rain sometimes prevents access to Oia or delays the sunset viewing. One reviewer mentioned, “Rainy day did not go to OIA or see the sunset,” which is worth considering if you’re visiting outside of the peak summer months.
What’s Included and What’s Not
The package covers air-conditioned transportation, wine tastings at two wineries, food assortments, a guide, and hotel pickup/drop-off. The inclusion of food is a nice touch, even if the offerings are modest, and most find the guide helpful and knowledgeable.
What’s not included? Personal expenses and additional food or drinks beyond the tastings are on you. The cost is quite reasonable given the experience, especially considering the scenic and educational aspects.
Planning evening activities? Here are other after-dark options we've examined in Santorini
- Traditional Greek Night live Music & Dinner Show in Santorini
- Santorini Luxury Catamaran Sunset Cruise with BBQ, Drink and Transfer
- Santorini Sunset Sailing Cruise: Dinner, BBQ, Open Bar, Transfers
- Romantic Sunset Catamaran Caldera Cruise incl. Meal & Drinks
- Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer
- Santorini Wine Adventure with 12 Wine Tastings, Tapas and Sunset
Weather and Timing Considerations
The tour departs at 3:30 pm, positioning you perfectly for the sunset. The timing aligns well with the natural light and sunset schedule, though weather can impact the experience. Rain can cut the Oia visit short, as some reviews have noted, but the wine tastings at the wineries are indoors and unaffected.
Getting picked up at your hotel is a big plus, especially since some guests have pointed out that transportation back from Oia can be tricky if the roads are hilly or weather is poor. That said, the overall service seems efficient, with most reviewers happy with the logistics.
Authentic Feedback From Travelers

Reviews paint a mostly positive picture. One guest called it a “Great experience,” feeling that expectations were exceeded, even when the weather was less than ideal. They appreciated the wine experiences and the group’s small size, making for a relaxed evening.
On the other hand, some say the overall value might not match other tours they’ve tried. One reviewer felt the food was underwhelming for a nine-hour tour, but the wines and the sunset made up for it.
The knowledgeable guide was consistently praised, with guests noting that the insights about each winery and the wine museum added richness to the experience.
The Sum Up
All in all, the Winery – Oia Sunset Tour offers a well-rounded taste of Santorini’s wine culture, scenic beauty, and sunset magic. It’s a great pick if you’re after a small-group experience where you can learn, taste, and relax without feeling rushed. The views from Venetsanos and Oia are iconic, and the wine selections are thoughtfully curated.
While weather can be a factor and the food offerings are light, the value for the price is clear, especially considering the personalized feel and the stunning scenery. This tour suits wine lovers, sunset chasers, and those who want a memorable, less commercialized experience of Santorini’s highlights.
If you’re looking for a relaxed, scenic way to spend an afternoon and early evening, this tour might be just what you need. Keep an eye on the weather forecast, arrive with an open mind, and prepare to enjoy some fantastic wines and breathtaking views.
Winery – Oia Sunset Tour
“Rainy day did not go to OIA or see the sunset and we got finished much earlier than sunset. Good wine and informative. Though we go picked up at ou…”
FAQ

Is the tour suitable for children?
No, this is an adult-only experience, mainly because it involves wine tastings and a focus on adult beverages.
What time does the tour start?
It begins at 3:30 pm, which is ideal for catching the sunset in Oia.
How many people are in each group?
The tour is limited to a maximum of 15 travelers, ensuring an intimate and relaxed atmosphere.
Are the transportation arrangements included?
Yes, an air-conditioned vehicle provides pickup and drop-off service, making logistics straightforward.
What is the price per person?
It costs around $127.45, which includes tastings, visits, guide, and transportation—considered good value for this type of experience.
Will the weather affect the sunset viewing?
Yes, rain or bad weather can prevent or delay the sunset at Oia, but the winery visits remain unaffected indoors.
What’s included in the food?
Food assortments are provided, but based on reviews, they are modest and not the main focus of the tour.
Can I cancel if my plans change?
Yes, it’s free to cancel up to 24 hours in advance for a full refund.
All in all, if you’re craving a laid-back, scenic, and wine-filled late afternoon in Santorini, this tour offers a solid balance of views, education, and relaxed enjoyment.
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