9 Sunset Sailing Cruises in Santorini That Earn the Fare

1.Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset

★★★★★★★★★★5.0 · 1,694 reviews · 5 hours (approx.) · from $181Number one

Spend about five hours on a shared catamaran around Santorini, with hotel pickup, two swim stops, a Greek meal, white wine, Greek beer, soft drinks, and a towel. Choose a morning sailing or sunset cruise. Luxury options add views of Oia and Ammoudi Bay, though you stay aboard while passing them.

“Great mix of activities-sailing and stopping to swim. Crew very nice and hospitable. Not overcrowded”

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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 sailing Santorini’s caldera, swimming near the hot springs, Red Beach, and White Beach, then eating a BBQ meal with wine, soft drinks, and water. Captain Sakis and crew members Giannis and Orestis have been praised for their warm service. Choose the later departure for the best chance of seeing Oia’s sunset.

“Amazing cruise - great crew, great atmosphere, the views, the stops at the bays and the food were all perfect. The wine was probably the only thing I didn’t rate too highly but not enough to put me off. The sunset was incredible - worth every penny to go o this trip! Definitely recommend.”

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3.Romantic Sunset Catamaran Caldera Cruise incl. Meal & Drinks

★★★★★★★★★★4.5 · 328 reviews · 5 hours (approx.) · from $114

Spend about five hours aboard a small catamaran along Santorini’s caldera, with stops near Red Beach, White Beach, the thermal springs, and Oia. You get hotel pickup, towels, Greek barbecue, wine, beer, and soft drinks. The crew, including Yannis on some departures, keeps the mood friendly and relaxed.

“My boyfriend and I did this cruise tour at the end of April and overall had a great experience. Although it was extremely windy, a bit cold, and rainy at times, the crew made sure everyone had plenty of wine and was having fun. (They also supplied blankets, if needed.) The barbecue dinner was delicious and my boyfriend was grateful for the vegetarian option. It was too cold and drizzly for us to do the stop at the hot/tepid springs or swim much (I think only two or three people from the entire group opted to go for a short swim, and they reported it was chilly), but we still…”

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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 with a shared group, stopping at the volcano for a guided hike, Palea Kameni for warm spring swimming, and Thirassia Bay for a Greek buffet and wine. Guides such as Tito and Cesar add energy, while the sunset near Oia closes the day.

“Loved swimming at the warm springs but it did ruin my white bathing suit. Pays to read the notes! Sober was delicious. Be aware that you do pay for all drinks other than wine at dinner.”

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5.Sunset Caldera Sailing Cruise

★★★★★★★★★★5.0 · 96 reviews · 5 hours (approx.) · from $151

Sail from Vlychada with a small group of up to 10, passing Red Beach, White Beach, Akrotiri Lighthouse, and volcanic Palea Kameni. You’ll have time to swim, use included snorkeling gear, and enjoy a freshly prepared Greek meal with unlimited beer, wine, and soft drinks. Crew members named in feedback include Antonio, George, Maria, Christos, and Martha.

“Lovely trip. Sunset was beautiful. Swimming was fun. Was a small group so nice intimate setting. Food was tasty. Would recommend this tour for the sunset alone.”

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6.Santorini Caldera: Sunset Sailing Cruise with Meal

★★★★★★★★★★4.8 · 68 reviews · 5 hours · from $147

Spend five hours sailing from Vlychada Marina past Red Beach, White Beach, Mesa Pigadia, and the Akrotiri Lighthouse. Swim near volcanic shores, visit the hot springs around Palea Kameni, and eat a crew-prepared seafood barbecue with local wine. The small group is limited to 10, with pickup from several Santorini areas.

“Awesome afternoon, great people, Niko and Antonio are wonderful and the food was great. I recommend this 200%.”

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7.Santorini Oia: Private Sunset Catamaran Cruise with BBQ & Drinks

★★★★★★★★★★5.0 · 39 reviews · 6 hours (approx.) · from $898

Spend about six hours aboard a private catamaran with Renieris Santorini Sailing Center. Swim at Thirassia, Palea Kameni, Mesa Pigadia, White Beach, and Red Beach, then watch the sunset over Santorini with Greek salads, BBQ seabream or chicken, vegetarian food, wine, beer, and soft drinks. Pickup is offered.

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8.Motor Yacht Sunset Cruise with 5-Course Dinner

★★★★★★★★★★4.5 · 35 reviews · from $80Cheapest deck

Sail from Vlihada through Santorini’s caldera on the Oniro yacht, passing red and white beaches, the lighthouse, and both volcanoes. You’ll swim near the volcano and Mesa Pigadia, then enjoy a five-course meal with wine, beer, soft drinks, coffee, and tea. Hotel pickup and small groups are included.

“Staffs were very attentive expecially Spyros who did a great job explaining us about the sites and chilling with us whenever he could. Food was delicious, there was no music but we carried a speaker and played it through out. Sunset isn't from Oia but this was majestic and beautiful.”

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9.Catamaran Cruise, Winery, & Oia Sunset Combo Tour

★★★★★★★★★★4.7 · 28 reviews · 10 hours · from $212

Spend five hours on a catamaran with swimming stops, barbecue, Santorinian wine, and snorkeling gear, then visit Venetsanos Winery and Mesa Gonia’s Wine Museum. Your day ends at Oia’s Sun Spirit Bar for sunset. Cruise guiding is in English, while the bus portion is offered in English and Spanish. Niki has received warm praise for the wine tour.

“We had the most wonderful time on this excursion! Pickup was prompt and efficient. The catamaran sail was so much fun. I wish we could have spent a little more time at the swimming spots because they were so beautiful. The wineries were incredible and our the tour guide was very informative.”

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