7 Dining Experiences in Santorini Weighed Up Side by Side

1.Santorini Wine Stories: Sunset Tour with Tasting & Dinner

★★★★★★★★★★5.0 · 1,285 reviews · 5 hours (approx.) · from $209Our pick

Join a sommelier-led evening through Santorini’s vineyards, with visits to three wineries, 10 local wines, cellar visits, dinner, and a sunset stop. Guides including Nicolas, Constantine, and Rafael explain Assyrtiko, Nykteri, Vinsanto, and the island’s volcanic soil. Pickup, water, wine, food, and taxes are included.

“This was the perfect excursion for our visit to Santorini! Constantine was our Sommelier. He is very knowledgeable about the Greek wines and the vineyards. I am not a wine connoisseur by any means, but in our tasting, I found multiple wines that I liked. The sunset was magnificent at the winery and we had the “best table in the house”! Amazing!”

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2.Kamari: Greek Show, Buffet Dinner, and Drinks at Dimitris

★★★★★★★★★★4.6 · 474 reviews · 3 hours · from $71Best value

Spend three hours at Dimitris restaurant in Kamari for a lively Greek night with a buffet, unlimited wine, beer, soft drinks, and water. Costumed dancers perform zorba and syrtaki, musicians play violin and bouzouki, and you can join the dancing and smash a plate for good luck. Seating is first come, first served.

“Such a fantastic night, they get everyone involved by getting up to dance, very fun and lively. Great performance from the musicians and dancers, great food & drink.”

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3.Romantic Sunset Caldera Cruise with Dinner

★★★★★★★★★★4.1 · 457 reviews · 1 day · from $76

You’ll ride a shared Kamari Tours bus to Athinios Port, board the King Thiras, and cruise beneath Santorini’s caldera with an English or Greek-speaking guide. Expect welcome drinks, volcano views, a buffet of Greek food, and a sunset stop at sea. Bring a jacket, and carry cash for the bar.

“Great cruise seeing Santorini from the water. The food was very good as well.”

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4.Perivolos Beach: Sun-Bed Experience FortyOne Bar Restaurant

★★★★★★★★★★4.8 · 449 reviews · 1 day

Book a private beach setup for up to two people at FortyOne Bar Restaurant on Perivolos Beach. Choose two large sunbeds or a cabana for up to four, then order lunch, sushi, cocktails, wine, and local dishes at your bed or in the dining area. Beach service begins at 10:00 AM, with towels, showers, and changing facilities included.

“Pretty standard, very beautiful beach & they have the best chairs I’ve seen on all of the beaches next”

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5.Santorini Caldera Sunset Sailing Cruise with Dinner and Wine

★★★★★★★★★★4.5 · 208 reviews · 6 hours (approx.) · from $96

Spend about six hours sailing Santorini’s caldera with a shared group, visiting the volcano and Palea Kameni hot springs before a Greek buffet dinner and sunset near Oia. Guides such as Tito and Cesar have led the trip. Pickup is available, but confirm the time and meeting point carefully.

“Lovely cruise, very efficient pick up service, beautiful views and experiences, and the staff were very friendly and had great energy/service”

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6.Santorini Caldera: Sunset Cruise with Dinner

★★★★★★★★★★4.1 · 59 reviews · 4 hours · from $76

Spend four hours on an English-led cruise from Santorini’s Athinios Port to Nea Kameni, Palea Kameni, Thirasia, and the cliffs below Oia. You’ll walk to a volcanic crater, approach sulfurous springs, eat a crew-served buffet, and finish with sunset views in Oia. Transport, dinner, and the boat ticket are included, but drinks cost extra.

“The caldera cruise was very good. Collection and drop off is good too. The guide is welcoming. There's a welcome wine drink when you aboard, taste good. The food served is good too as we're not picky. By the way, refreshments are not included, you have to buy it there and they prefer cash or card, I saw a few paying by card. Cruise in the month of October is relaxing maybe because there's a small number of people on the boat that time. I brought my cardigan but it's not that cold when the sun sets, just nice and fresh. And you get a good view of the sunset…”

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7.Night Hike, Wine Tasting, and Greek Dinner

★★★★★★★★★★4.5 · 40 reviews · 3 hours · from $182

Walk from Fira toward Imerovigli on Santorini’s quiet evening trail with an English-speaking guide such as Anastasios. Stop for sunset views over the Caldera and volcano, then watch the island light up before tasting four local wines, including Assyrtiko and Vinsanto, over a Greek dinner. Hotel pickup and return are included.

“The food and drinks were great! Guide was very informative and helpful throughout the tour. We loved the interaction with restaurant owner/chef and servers. Made us feel welcome! Would highly recommend this tour!”

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