15 Sunset Wine Experiences in Greece the Drive Pays For

1.Top Sights Day Trip, Wine Tasting, & Oia Sunset

★★★★★★★★★★4.6 · 2,492 reviews · 9 hours · from $61Our pick

Spend nine hours touring Santorini by coach with an English-speaking guide such as Mary, Yannis, or Kim. Visit Profitis Ilias, Pyrgos, Emporio, and Perissa Beach, taste three local wines, then watch the sunset in Oia. Hotel pickup and drop-off are included, but lunch and drinks are extra.

“A very interesting and informative day Yannis was knowledgeable witty and helpful. Reteraunt reccomended at beach was great. Overall we would we would definitely recommend this trip Thanks Manuel and Jan Lima”

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2.Santorini Wine Adventure with 12 Wine Tastings, Tapas and Sunset

★★★★★★★★★★5.0 · 1,715 reviews · 4 hours (approx.) · from $181Top rated

Visit three Santorini wineries, taste 12 local wines, and sample cheese, cold cuts, olives, and bread. Your guide explains the island’s volcanic vineyards, basket-trained vines, and wine-making methods. Choose the sunset option for a final tasting and tapas plate at Santo Wines, with caldera views and photos taken by your guide.

“Marina was an incredible guide - providing us with info and insights. The three wineries we visited were lovely - we enjoyed the wines and charcuterie at each of the locations! Final stop gave us an amazing sunset along with the wines!”

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

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

Spend about five hours visiting three Santorini wineries with a sommelier guide such as Nicholas, Constantine, or Rafael. Taste 10 local wines, including Assyrtiko, Nykteri, and Vinsanto, tour cellars, enjoy a Greek dinner, and finish with a sunset view. Hotel pickup and return transportation are included, with groups capped at eight.

“Our guide, Nic, was extremely friendly and knowledgeable. Each vineyard we visited was beautiful and served nice wines. The price was very reasonable for all we got. It was a wonderful experience!”

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4.Small-Group Sunset Wine Tour with Santo Winery

★★★★★★★★★★4.9 · 801 reviews · 4 - 4.5 hours · from $212

Spend 4 to 4.5 hours visiting three Santorini wineries with an English-speaking guide and up to nine other people. Taste Assyrtiko, Nykteri, Vinsanto, reds, Greek cheese, and tapas while learning why Santorini’s vines grow close to the ground. The evening ends at Santo Winery, with wine and sunset views over the volcano.

“Outstanding evening with great people and fantastic guide: Kostis!! The 3 wineries, with such great explanation of history and insight on the future wine industry in Santorini. The view from Santo wine capped off the night beautifully!”

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5.Crete: Land Rover Safari with Sunset Viewing, Dinner, & Wine

★★★★★★★★★★4.9 · 395 reviews · 6 hours · from $99

Join Safari Club Crete for a six-hour Land Rover trip into Crete’s mountains. Your guide, often George, Kosta, Chris, Mike, or Yiannis, takes you along rocky roads to villages, local tastings, and a sunset stop with Prosecco and fruit. Finish with a traditional dinner, unlimited wine, and possibly Greek dancing.

“The trip was very adventurous, lovely ride up the mountains up the rocky road. George our guide was very knowledgeable and great at taking our beautiful Sunset photos of us. Amazing Sunset. Tour around the villages was fabulous little villages. The Taverna food and drink was delicious and there were plenty of it. The whole trip was magical. So worth the money. Throughly Enjoyed it.”

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6.Santorini Sunset Wine Tour with Santo Winery Views

★★★★★★★★★★5.0 · 342 reviews · 4 hours (approx.) · from $205

Spend about four hours visiting three Santorini wineries with an English-speaking wine guide and pickup from your hotel or Airbnb. Taste mainly Assyrtiko whites and dessert wines, learn local winemaking, and finish at Santo Wines with cheese, cold cuts, tapas, and sunset views. Guides such as Angelo, Vassi, Marina, and Kristina are known for warm, lively hosting.

“Loved our sunset wine tour! Angelo was knowledgable, friendly and entertaining. We had a great time, learned a lot, and drank a lot of wonderful wines.”

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7.Rhodes: Sunset Cruise with Unlimited Aperol, Beer, and Wine

★★★★★★★★★★4.8 · 323 reviews · 3 hours · from $53

Join a three-hour sunset cruise from Mandraki Harbour with Paulos and the crew. Swim near Kallithea Springs, listen to music, and enjoy unlimited Aperol Spritz, beer, wine, water, and soft drinks. The boat returns as the sun disappears over Rhodes. Food is not included, though a Greek BBQ upgrade may be available at check-in.

“I got engaged on this trip, the setting was too good, the sunset was amazing, too bad I can’t post photos here! Honestly, one of the best cruises I have ever done!”

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8.Wine Tasting Tour & Sunset Viewing

★★★★★★★★★★4.8 · 255 reviews · from $192

Spend about five hours visiting three Santorini wineries with an English-speaking guide such as Gregory, Michael, or Constantina. Taste 12 to 15 wines, including Assyrtiko and Vinsanto, with local cheese, bread, meats, and dips. A small group of up to 10 rides in an air-conditioned minivan and ends with a sunset stop.

“Amazing tour! Amazing guide Gregory! Very knowledgeable and so nice. It was so fascinating to learn about the history of wine in Greece.”

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9.Rhodes: Sunset Cruise with Live Music, Wine & Greek Buffet

★★★★★★★★★★4.6 · 236 reviews · 3 hours · from $53

Join Romantika Dreams at Mandraki Port for a three-hour evening cruise along Rhodes’ east coast. Swim and snorkel near Kallithea Springs, enjoy a Greek buffet with local white and rosé wine, then watch the sunset at sea with live music. The boat returns around 9pm. Bring swimwear, sunscreen, a towel, and a jacket.

“Staff were all so friendly and helpful, lovely boat, drinks were good and atmosphere also amazing. Food was also lovely and fresh, would definitely recommend.”

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10.Lindos: Sunset Cruise with Unlimited Aperol, Beers & Wine

★★★★★★★★★★4.8 · 224 reviews · 1h 30m · from $47Best value

From Vlycha Beach, you’ll board a 90-minute evening cruise toward Lindos and St Paul’s Bay. The English-speaking crew serves unlimited Aperol Spritz, beer, white wine, and soft drinks while chill music plays. Expect a relaxed sunset outing focused on sea views and photographs, not a long swimming or snorkeling trip.

“The 3 hour cruise around Lindos was wonderful. Relaxing swims, a very good experience and led by an excellent crew. I wouldn’t change anything!”

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11.Faliraki: Sunset Cruise with Unlimited Aperol, Beers & Wine

★★★★★★★★★★4.8 · 212 reviews · 1 hour · from $47

Meet your English-speaking host at the small church in Faliraki Harbour for a relaxed sunset sail to Anthony Quinn and Ladiko bays. You will enjoy unlimited Aperol Spritz, beer, white wine, and soft drinks with chill music aboard a comfortable boat. The cruise is wheelchair accessible and costs $47 per person.

“Incredible Faliraki evening out! We boarded at 7pm and sailed into golden hour with refreshing drinks!”

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12.Argostoli: Sunset Cruise with Swim Stops, Dinner, and Wine

★★★★★★★★★★4.9 · 205 reviews · 4 hours · from $53

Join Queen Bee Boat Trips in Argostoli for a four-hour evening cruise led by a friendly crew and captains such as Petros or Yannis. Swim near Vardiani Islands or Xi Beach, use paddle boards and snorkeling gear, then eat homemade moussaka and Greek salad with wine while the Kefalonia sunset fades into the sea.

“Tha captain and all the crew were very friendly, the food was lovely and so was the wine. Best trip on Kefalonia in my opinion.”

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13.Wine Tour with Sunset in Oia

★★★★★★★★★★4.6 · 199 reviews · 5 hours · from $129

Spend five hours visiting Hatzidakis Winery and the Santorini Wine Museum, tasting about eight local wines with a guide such as Mary, Susanna, or Yiannis. Learn how Santorini grows grapes in volcanic soil, then finish at Sun Spirit in Oia with a reserved sunset table, wine, and snacks. Hotel pickup and drop-off are included.

“while we went thru the museum and the vineyards, the icing on the cake was the sunset view point at Oia. thank you Souzana for being patient and taking us through the place. extremely knowledgeable and approachable listening to each of us and providing answers.”

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14.Sunset Cruise with Greek BBQ & Unlimited Aperol Spritz, Beer Wine

★★★★★★★★★★4.5 · 159 reviews · 3 hours (approx.) · from $48

Set sail from central Rhodes with hosts including Panos and Katia, cruise past the Old Town walls, stop at Kallithea Springs for swimming and a freshly prepared Greek barbecue, then return beneath the sunset with unlimited Aperol Spritz, beer, and wine. The boat holds up to 80 people and returns to the starting point.

“Great few hours spent on the boat. The staff were so friendly, the drinks flowed and the BBQ was tasty and a good amount. We swam off the back of the boat, it was cold but when in Rhodes..... sunset was beautiful, really good value for money too. Loved the whole thing and would highly recommend.”

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15.Heraklion: Dia Island Romantic Sunset Cruise with Wine

★★★★★★★★★★4.8 · 144 reviews · from $86

Join DanEri Yachts for a 3.5-hour semi-private catamaran cruise from Heraklion to Dia Island. Captain Sergei and the English-speaking crew serve Prosecco, Cretan wine, Greek beer, fruit, cheese, and cold cuts. You will have time to swim, snorkel, paddleboard, fish, and watch the sunset before returning to port.

“Awesome trip! The team was very friendly and cared a lot about our needs. The bay at Dia island was greatful and the water was very clear. The sunset was also beautiful. It was a special experience which we can recommend to everyone.”

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