Caldera Sailings in Santorini: 15 Volcano Days on the Water

1.Catamaran Caldera Cruise with Meal and Drinks

★★★★★★★★★★4.7 · 2,255 reviews · 5 hours · from $70Number one

Spend five hours aboard a modern catamaran sailing from Ammoudi Bay past the caldera, Aspronisi, the Venetian Lighthouse, Mesa Pigadia, White Beach, and Red Beach. Swim near the volcano and at coastal stops, enjoy a fresh Greek BBQ with wine and soft drinks, and watch the sunset on selected departures. Pickup may be available.

“The best cruise experience in my entire life, everything is the best from pick up from our hotel until we were brought home.. The entire team is amazing, they are all well dedicated to their work, they are all very nice and very kind, the swimming stops are amazing, we swam on sulfur water near the volcano, in the red and white beach. The water in santorini is the most beautiful, im a traveller and loves to swim very much and love to cruise but this was the most beautiful,thank you for the once in a lifetime memories and experience, The team took good care of us, entertained us not…”

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2.Catamaran Caldera Cruise with Meal and Drinks

★★★★★★★★★★4.8 · 980 reviews · 5 hours · from $112

Sail Santorini’s Caldera for five hours on a luxury catamaran with swimming stops at Red and White Beach, volcanic hot springs, snorkeling gear, towels, BBQ, Greek appetizers, local wine, and an open bar. Choose a daytime or sunset departure, with hotel pickup available across the island.

“The yacht tour was amazing with our toddler . Guides were very helpful and we were allowed to snorkel at several stops. Definitely will do it again.”

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3.Caldera Classic Catamaran Cruise w/ Meal & Drinks

★★★★★★★★★★4.8 · 379 reviews · 5 hours · from $123

Spend five hours sailing from Vlichada Marina to Red Beach, White Beach, Mesa Pigadia, Akrotiri Lighthouse, and Nea Kameni. You’ll swim, snorkel, eat a fresh Greek barbecue, and enjoy unlimited local wine, beer, soft drinks, and water. The English-speaking crew, including guides such as Fay, Enrico, and Anastasia on past departures, also share island stories and help with photos.

“Good experience. Everything is good. Kindly staffs. Paitent driver. Delishious food. Loveeeee it！”

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4.Santorini All-inclusive Catamaran Cruise with Thirassia Stop

★★★★★★★★★★4.5 · 348 reviews · 5 hours (approx.) · from $193

You’ll sail from Amoudi Bay to Thirassia, the volcanic islands, hot springs, White Beach, Red Beach, and Vlychada aboard a modern catamaran limited to 16 people. Expect hotel transfers, a freshly prepared meal, Santorini wine, beer, soft drinks, snorkeling gear, towels, and time to swim. Sunset departures add the island’s best finale.

“This was a very nice excursion; wonderful staff, very good food which was cooked and prepared on board!”

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5.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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6.Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

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

Spend about five hours on a catamaran from Vlychada Marina, visiting Red and White Beach, the caldera, Palea Kameni, and Nea Kameni. Choose a 10am day cruise or a 3pm sunset sailing. Expect swimming, snorkeling, barbecue seafood and steak, unlimited drinks, and crew members such as Maria, Joe, Dimitris, or Nancy depending on the sailing.

“This was the 4th time we have been to Santorini and wanted to do something different. This was by far our best excursion in any port for the trip, and the crew and food were phenomenal. We are well seasoned travelers over 40 cruises and have done many catamaran trips but all those others paled in comparison. Great trip, and well worth the cost.”

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7.Caldera Luxury Catamaran Cruise w/ Meal & Drinks

★★★★★★★★★★4.9 · 237 reviews · 5 hours · from $148

Spend five hours aboard a clean, roomy catamaran from Vlichada Marina. Swim at Red Beach, White Beach, Mesa Pigadia, and Nea Kameni, then enjoy a fresh Greek barbecue with local wine, beer, soft drinks, and water. Hotel transfers, towels, snorkeling gear, and an English-speaking crew are included.

“We had a wonderful experience on this trip. The pick up was smooth and transfer to the boat was pleasant. The staff on boat were wonderful and made it a lovely experience from start to finish. The food was delicious and so fresh, cooked on a BBQ right on the back of the boat. Would highly recommend this tour.”

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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 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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9.Comfort Max Catamaran Caldera Cruise with BBQ and Drinks

★★★★★★★★★★4.5 · 191 reviews · 5 hours (approx.) · from $72

Sail from Ammoudi Bay for about five hours aboard the Comfort Max catamaran. You’ll pass the volcano, Indian Rock, Venetian Lighthouse, and Red Beach, with time to swim or snorkel near Mesa Pigadia. A Greek BBQ, mezedes, Santorinian wine, soft drinks, and water are included. Day and sunset departures are available, with hotel pickup as an option.

“It was super fun, the most beautiful sunset ever, the staff were great, the boat is perfect, the food was perfect,. The only problem was they sold too many tickets. There were two families on the boat that didn’t have a place to sit.”

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10.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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11.Beautiful Day Catamaran Caldera Cruise incl. Meal & Drinks

★★★★★★★★★★5.0 · 91 reviews · 5 hours (approx.) · from $114

Set sail from Ammoudi Bay on a small catamaran cruise limited to 16 people. Swim at the hot springs, Mesa Pigadia, and Red Beach, then enjoy a Greek BBQ, wine, ouzo, beer, and soft drinks on board. Captain Zannis and the crew guide a relaxed five-hour outing, with pickup available from your accommodation.

“It’s always a treat to do a boat trip to see places from the water and this did not disappoint ! Early season and we were treated to being on the boat by ourselves. The crew were very attentive - Captain Zannis the best - spectacular and close up action of the coastline. 3 swimming spots with snorkeling equipment and lunch! We had a blast”

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12.Private Caldera Cruise with Power Catamaran ENJOY incl. Meal & Drinks

★★★★★★★★★★5.0 · 79 reviews · 3 to 5 hours (approx.) · from $452

Spend 3 to 5 hours on a private Santorini catamaran with pickup, swimming stops, snorkeling gear, SUP, Greek appetizers, barbecue, wine, beer, and soft drinks. Your crew may include Phillip, Kostas, Adam, or Gianni, and the route can be adjusted to suit your group.

“My mother and I enjoyed ourselves so much! Phillip was and his deckhand were very informative about the islands and its history. & the food was on point, I will definitely book again!”

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13.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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14.Dream Catcher 5-hour Sailing Trip in the Caldera

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

Sail from Vlihada Marina past Akrotiri, Red and White Beaches, the Indian Head Mountain, and the Venetian Lighthouse. The 5-hour cruise includes swimming, snorkeling, hot springs, a BBQ lunch, beer, wine, sodas, and hotel pickup. Guides such as Dimitris explain the Caldera, while the crew handles the sailing.

“We did this tour when coming to Santorin with a cruise ship and enjoyed it very much. As the catamaran is quite large, it can go out into deeper waters and while it can get wet then, it is much fun. There are several stops, one at a private beach with a great BBQ, very cool location. As I realized after the booking that the time might get tight to reach our cruise in time, I asked one (!) day before the actual excursion whether there was any solution and we were offered a private trip back after the BBQ. Excellent service, very customer oriented. Furthermore, everything went smoothly with…”

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15.Santorini Caldera Private Sailing Boat Cruise

★★★★★★★★★★5.0 · 48 reviews · 5 hours (approx.) · from $961 per boat

Sail privately from Vlychada with up to four people, stopping at Red Beach, White Beach, the volcano, hot springs, and Thirassia. Your crew handles the route, swimming gear, towels, drinks, and a barbecue-style meal with seafood or vegetarian choices. Hotel pickup and sunset departures are available.

“Amazing! Must do when traveling to santorini. Our captain looked like jack sparrow, it was just absolutely gorgeous”

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