Santorini Sunset Wine Tour with Santo Winery: Review and What to Expect

It is one of the best-reviewed wine tours on the island, with a 4.9 rating from nearly 900 reviews. Its guides and transport both score 5.0/5 on the listing, and value for money scores 4.8. Guides praised by name in recent reviews include Mary, who is mentioned most often, and Angelo, Kristine, Giannis, Elena and Marina.

We haven’t taken this tour ourselves. For this review we went through the current listing and recent traveler reports, looking closely at complaints about the pickup, the size of the pours and how busy Santo Wines gets at sunset. There are five things worth knowing before you book:

• The pours are tasting-size: four wines at each winery, 12 in total.
• The food changes from stop to stop, and the platter at Santo Wines gets the best reports.
• Santo Wines is busy at sunset, and not every table faces the view.
• Pickup is by hotel, but in car-free lanes you are collected from a nearby corner instead.
• Door to door, the afternoon can run longer than the listed 4 to 4.5 hours.

The listing mentions some of this, although the short summary doesn’t make all of it obvious. If you want a small-group tasting tour with transport handled and a sunset stop at the end, this one fits that brief well. If you want large pours, a quiet winery terrace or a proper dinner, you may find the $205 price harder to justify.

Five tips before you book

• Check your pickup point the day before. If your hotel is on a pedestrian lane, common in Oia and Imerovigli, the operator collects you from the nearest spot a vehicle can reach. The pickup problems in the reviews came from travelers waiting at one spot while the driver waited at another.
• Tell the operator if friends are staying at another hotel. One recent reviewer couldn’t join friends who were staying elsewhere, and only met up with them at the last stop. It isn’t guaranteed that you can ride together, but it’s worth asking.
• Expect a tasting, not a night of drinking. Each winery pours four wines, and one recent reviewer called them the smallest servings they had seen. Other reviewers describe the pours as generous.
• Ask whether a caldera-facing table is available at Santo Wines. One recent reviewer’s group was seated to the side, some distance from the sunset view.
• From mid-October, check the pickup time against the sunset. Sunset in mid-November is at about 5:10 pm. With a 4 pm start and Santo Wines as the last stop, confirm with the operator when you will get there.

How the afternoon runs

The listing gives a start of about 4 pm, adjusted to where your hotel is on the pickup route, and a length of 4 to 4.5 hours. The itinerary has three tastings of about an hour each, and the drives and pickups come on top. One reviewer was dropped off five hours after pickup, and another called it a six-hour tour. Plan dinner for later in the evening. Some travelers say the snacks were substantial enough that they didn’t need much afterwards.

Groups are capped at 10 guests, in an air-conditioned van. Expect mostly dry whites and dessert wines, with some reds, reflecting the styles Santorini is best known for. You can buy bottles at the wineries if you want to take some home.

The order and the first two wineries can change. The listing’s itinerary names Domaine Sigalas and Estate Argyros, while its description also mentions Gaia and Anhydrous, and the operator’s own site adds Gavalas. Santo Wines is always the last stop. You’ll find out which cellars you’re visiting on the day.

The listing says the tour runs from May to October. At the time of writing, the booking calendar also shows dates into mid-November 2026 and from April 2027, and the operator’s own website gives April to November. Nothing is offered from December to March.

Stop 1: The Vineyard and the First Winery

The afternoon starts with a walk into a vineyard, which several travelers mention as one of the highlights. The vines are trained into low baskets close to the volcanic soil, which shelters the grapes from the wind. One reviewer called this introduction their favorite part and wished there had been more of it.

The first tasting is usually at Domaine Sigalas or Estate Argyros, with four wines and a plate of snacks. Food at the first two stops gets mixed reviews, ranging from cheese and crackers to small savory bites. If the food matters to you, eat something light before pickup.

Stop 2: The Second Winery

The middle stop varies more than the others: Gaia, Anhydrous, Argyros or Sigalas, depending on the day. Gaia is mentioned positively in several recent reviews, particularly for the wines. The format is the same as at the first stop: four wines, with the guide explaining each one before you move on.

One traveler found three wineries too many and suggested a two-winery option. If Santo Wines and the sunset are your main priorities, a shorter tasting tour may suit you better.

Stop 3: Santo Wines at Sunset

Santo Wines sits on the caldera rim above Pyrgos, and its terrace is the main draw of a sunset tour. Recent reviews describe the view as the highlight of the day, and the platter served here gets the best food reports of the three stops. One reviewer described charcuterie, cheese and jam.

Santo Wines also gets busy at sunset, and other tours arrive around the same time. One reviewer found it hard to hear the guide at the busier wineries, another said the last winery was too crowded and noisy, and a third had a group table off to the side, some distance from the view. One reviewer said all of the operator’s groups gathered here for the sunset, which is how they met up with their friends.

If a quiet terrace matters more to you than this particular view, consider a smaller-winery tour instead (see the verdict below). If you do book, ask your guide whether your group can sit facing the caldera. Our Santo Wines guide covers the winery itself in more detail.