6 Sunset Cruises in Santorini to Build a Day Around

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

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

Visit three Santorini wineries with a sommelier guide such as Nicholas, Constantine, or Rafael, tasting 10 local wines including Assyrtiko and Vinsanto. You’ll tour cellars, learn how volcanic soil shapes the island’s wines, enjoy dinner with Greek dishes, and finish with a sunset view. Pickup and drop-off are included.

“Rafael was absolutely the most delightful and knowledgeable guide and host on this thoroughly enjoyable evening. So much fun, unbelievable scenery and meeting new friends was just magical!”

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2.Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

★★★★★★★★★★4.5 · 1,105 reviews · 5 hours (approx.) · from $95

Spend about five hours aboard a catamaran with hotel pickup, swimming stops at the hot springs, Red Beach, and White Beach, plus a BBQ, wine, soft drinks, and music. Captain Sakis and crew members Giannis and Orestis have been praised for their friendly service. Choose the later departure if seeing sunset near Oia matters most.

“Overall it was ok. The food was good along with the views. Music was load and it could’ve been shorter. Those looking for a quiet ride around seeing the sites this is not for you.”

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3.Santorini Luxury Catamaran Sunset Cruise with BBQ, Drink and Transfer

★★★★★★★★★★5.0 · 310 reviews · 5 hours (approx.) · from $157

Spend about five hours aboard the Ipanema 58, a spacious Santorini catamaran limited to 20 people. Swim near the hot springs, snorkel by Red and White Beaches, eat a Greek barbecue, and watch the sunset. Pickup, drinks, towels, snorkeling gear, and an English-speaking crew are included.

“The crew was AMAZING!! The catamaran was a highlight of our vacation!! Gorgeous view, delicious food and an awesome crew!!!”

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4.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, hiking the volcano, swimming near Palea Kameni, eating a Greek buffet, and watching sunset near Oia. Guides such as Tito and Cesar have led the trip, while the shared boat, swim noodles, pickup option, and lively return ride make this a social outing rather than a quiet private cruise.

“We had an amazing time! Staff and crew were very nice and knowledgeable. One of the staff members got us all to join him in dancing at the end. We really enjoyed our day.”

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5.Santorini Caldera: Sunset Sailing Cruise with Meal

★★★★★★★★★★4.8 · 65 reviews · from $131

Spend five hours on a small-group sailing cruise from Vlychada Marina, passing Red Beach, White Beach, the lighthouse, volcanic islands, and the caldera cliffs. Swim near Mesa Pigadia and Palea Kameni, enjoy a seafood barbecue with local wine and beer, and watch the sunset at sea. Hotel pickup and drop-off are included.

“This was so fun! I picked this tour because it was an actual sailboat and not a catamaran. The very competent crew had the sails up for most of the trip. It was awesome! We stopped for swimming twice. One of the swimming stops was at the hot springs, which was a nice experience. Swimming in almost hot ocean water near piles of volcanic rock was a very unique experience. That was definitely the highlight for me. The crew also dropped anchor here and fed us a delicious meal. We also had unlimited wine and beer. Yiannis, who is the company/boat owner picked us up from our hotel and dropped…”

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6.Santorini Caldera: Sunset Cruise with Dinner

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

You’ll cruise from Athinios around Santorini’s caldera, visit volcanic Nea Kameni, pause near Palea Kameni’s thermal springs, and stop at Thirasia. Dinner is served aboard, then a bus takes you to Oia for sunset. An English-speaking host leads the trip, with hotel pickup from selected meeting points.

“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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