Sailing in Santorini: The 15 Best Days Under Canvas

1.Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

★★★★★★★★★★5.0 · 1,170 reviews · 5 hours (approx.) · from $133Our pick

Sail Santorini’s coast on a spacious catamaran for about five hours, with stops at Red Beach, White Beach, the hot springs, and Palea Kameni. Enjoy a fresh Greek barbecue, unlimited drinks, snorkeling gear, hotel transfers, and an optional sunset viewed from the sea. Groups are limited to 20.

“Easy, kind, beautiful despite the weather! The drivers were great, staff was excellent, stops were lovely! Recommend!!”

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

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

Sail from Ammoudi or Athinios Port past the volcano, hot springs, Red Beach, and White Beach. You’ll swim, snorkel, eat a BBQ, and enjoy wine, soft drinks, and water. The later departure may include sunset views near Oia, with hotel pickup and return included.

“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.Sailing Catamaran Cruise in Santorini with BBQ, Drinks and Transfer

★★★★★★★★★★4.5 · 568 reviews · 5 hours (approx.) · from $95

Spend about five hours aboard a catamaran from Ammoudi or Athinios, with hotel pickup, swims at the hot springs, Red Beach, and White Beach, plus a generous BBQ lunch. The English-speaking crew provides wine, soft drinks, water, music, snorkeling gear, and views of Santorini’s volcano coast.

“"I went on this trip with my wife and kids, and I enjoyed every single moment. However, when I was taking a picture on the cruise, one of the crew members (driver)rudely told me that I was blocking the way. He could have said it more politely, which made me feel bad at first. But later, he apologized, and overall, it was a good experience."”

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4.Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

★★★★★★★★★★5.0 · 560 reviews · 5 hours (approx.) · from $145

Spend about five hours aboard the Dream Catcher catamaran, swimming near Red and White Beaches, soaking at volcanic hot springs, and eating a Greek BBQ with unlimited beer, wine, and soft drinks. Hotel pickup is included, and crew members such as Mike, Dimitris, Panos, or Captain Peter may lead the day.

“Amazing sailing trip around the island, stopping at the red beach and hot springs. Crew were fun and made it a very enjoyable experience. Food v tasty and no shortage of drinks”

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5.Santorini Luxury Sailing Catamaran Cruise with BBQ, Drinks and Transfer

★★★★★★★★★★4.5 · 422 reviews · 5 hours (approx.) · from $133

Set out from Amoudi Port on a catamaran limited to 20 people. Swim near Palea Kameni’s hot springs, White Beach, and Red Beach, then enjoy a Greek barbecue, wine, beer, and soft drinks. Hotel transfers, towels, snorkeling gear, and a restroom are included.

“The captain & crew were great!!! The food was excellent!!!! We had a great time !!!! We would definitely recommend this company! Thank you :)”

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6.Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

★★★★★★★★★★5.0 · 268 reviews · 5 hours (approx.) · from $229

You’ll sail from Vlychada Marina on a small catamaran with a crew such as Joe, Maria, Nancy, or Dimitris. Expect Red and White beaches, the caldera, volcanic hot springs, swimming, a seafood BBQ, wine, beer, and hotel transfers. Choose a daytime cruise or sunset departure.

“What a great experience. Highly recommended. The food was excellent, the crew very friendly. Joe its one of a kind.. He can cook .. I was with my wife and my 8 year old. This was the highlight of our trip. Thanks guys”

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7.Santorini Small-Group Catamaran Sailing Trip(BBQ,drinks, transfer)

★★★★★★★★★★5.0 · 215 reviews · 5 hours (approx.) · from $157

You’ll sail with up to 14 people from your Santorini hotel to the caldera, Palea Kameni, Red Beach, White Beach, and the hot springs. The crew prepares Greek barbecue onboard, with wine, beer, soft drinks, snorkeling gear, towels, and hotel return included.

“Captain Alex and crew were amazing! Food was delicious! We all had so much fun. Beautiful sunset at the end!”

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8.Santorini Caldera Sunset Sailing Cruise with Dinner and Wine

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

Spend about six hours on a shared boat with guides such as Tito or Cesar, hiking Santorini Volcano, swimming near Palea Kameni, eating a Greek buffet, and watching sunset near Oia. Pickup is optional, wine comes with dinner, and the hot springs require a 30 to 40 meter swim.

“Adventurous climb to the Volcano, comfortable sailing, entertaining crew, sumptuous food with free flowing wine and magnificent sunset, and of course the on board dancing….. can’t ask for more!”

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9.Santorini Sunset Sailing Cruise: Dinner, BBQ, Open Bar, Transfers

★★★★★★★★★★5.0 · 208 reviews · 5 hours (approx.) · from $133

Set sail from Vlychada Port at 3:00pm for a five-hour cruise past Red Beach, White Beach, Indian Rocks, the Venetian Lighthouse, and Santorini’s hot springs. Swim and snorkel at Mesa Pigadia, enjoy a Greek dinner, BBQ, and open bar, then watch the sunset on the return.

“Une expérience fabuleuse merci à l'équipage tout était parfait.la nourriture aussi .Le transfert aussi”

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10.Santorini Private Sunset Sailing Tour with Dinner, Drinks &Transfer included

★★★★★★★★★★5.0 · 145 reviews · 5 hours (approx.) · from $650

Sail Santorini’s volcanic coast aboard a private family-owned yacht with Captain George and crew. See Red Beach, White Beach, Palea Kameni, and Thirassia, then swim, eat a cooked-on-board Greek dinner, and watch sunset with drinks included.

“Our Captain George and First mate Ina, we’re top notch hosts on our private sunset tour. They allowed us to see all the brilliance of the Caldera and worked hard to avoid crowded areas. We enjoyed the beauty of the Caldera in its entirety while hearing personal tales of sea and love. Our adult children swam in a quiet spot with ocean life beneath. The food served was prepared with personal touch and attention. It was delicious and one of our favorite meals while in Santorini! We highly recommend this crew for your Sunset adventure!!!”

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11.Deluxe Santorini Sailing with BBQ and Drinks Shared Tour

★★★★★★★★★★5.0 · 137 reviews · 5 hours (approx.) · from $193

Sail Santorini’s caldera on a shared catamaran for about five hours, stopping near Red or White Beach, Palea Kameni, and Nea Kameni. Expect swimming, volcanic scenery, barbecue food, unlimited beer, wine, and soft drinks, plus pickup and drop-off. Some sailings are led by Captain Chris and Theo.

“Beautiful catermeran. Friendly and professional crew who offered excellent service. Fabulous sunset tour with the family sailing around Santorini. It was advertised so we were expecting a bbq. There were 2 on board but unfortunately not. The food was delicious but pre prepared earlier that day. Fortunately we brought our towels as they were not provided as mentioned. With a couple of exceptions overall a fantastic day and would highly recommend.”

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12.Sunset Caldera Sailing Cruise

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

Sail from Vlychada with a maximum of 10 people, passing Red Beach, White Beach, Akrotiri Lighthouse, and Palea Kameni. Expect a freshly prepared Greek meal, unlimited beer, wine, and soft drinks, snorkeling gear, hotel pickup, and a sunset over the Santorini Caldera.

“Fantastic! The views were phenomenal, the tour guides were pleasant and kind, food was unbelievable. Highly recommend!”

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13.Santorini Private Daytime Sailing Cruise with Meal, Drinks &Transfer included

★★★★★★★★★★5.0 · 73 reviews · 5 hours (approx.) · from $649

Set out from Vlychada at 10 am on a private yacht with Captain George, stopping at Red and White beaches, the volcanoes, hot springs, Thirasia, and Aspronisi. You’ll swim, hear island stories, enjoy drinks, and eat a homemade meal prepared onboard.

“Amazing experience!!! We had so much fun out there had food and watched the fireworks. I highly recommended booking this trip!”

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14.Santorini Caldera: Sunset Sailing Cruise with Meal

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

Board at Vlychada Marina for a five-hour sailing trip past Red Beach, White Beach, Mesa Pigadia, Akrotiri Lighthouse, and the volcanic islands. Swim near Palea Kameni, enjoy a crew-prepared seafood barbecue with local wine, and watch the sunset from the Aegean. Hotel transfers and a group of up to 10 are included.

“I had a really fun, relaxing day. Crew were amazing - very friendly and helpful - the food was great and the trip itself very beautiful. Would definitely recommend!”

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15.Dream Catcher 5-hour Sailing Trip in the Caldera

★★★★★★★★★★4.7 · 61 reviews · 5 hours · from $147

Spend five hours aboard the Dream Catcher catamaran, sailing from Vlihada Marina past Akrotiri, Red and White Beaches, the Indian Head Mountain, and the Venetian Lighthouse. Swim near private bays, visit the hot springs, enjoy a barbecue lunch with drinks, and return with views of the volcanic islands.

“The captain and boat crew were very friendly and focused on the safety and comfort of the guests. A delicious lunch was prepared by the cook The experience exceeded the expectations. Crew explained the various key points and history of the Caldera. I will definitely recommend this experience to family and friends”

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