Greece · SAILING TRIPS IN SANTORINI

The 15 Best Sailing Trips in Santorini

20 tours  ·  from $96 per person

The good sailing trips in Santorini go weeks ahead and the great ones go first. Below: 15 to book early, what each includes and how they differ.

Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer - Red Beach: Santorini’s first swimming stop
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Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

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

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

Review of Santorini’s five-hour luxury catamaran cruise with swimming, snorkeling, Greek BBQ, drinks, hot springs, and sunset views.

“Such a fun tour. Swimming in the hot springs was a unique experience and the waters around the island were so clear it. Got to see a lot of fish. The food was also super delicious!”

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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - Passing the volcano and Palea Kameni
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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

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

★★★★★★★★★★4.5 · 1,105 reviews · 5 hours (approx.) · from $96Best value

Review of Santorini’s 5-hour sunset catamaran cruise with swimming, hot springs, BBQ, drinks, hotel pickup, and practical booking tips.

“Sunset tour was absolutely amazing. Stopped at a couple of places to snorkel and the water was so clear you could see down 30’. Food was good and plenty of it. Met very nice people and the whole boat had a great time listening to music and dancing. Sunset was fantastic as pretty much all sunsets in Santorini are.”

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Sailing Catamaran Cruise in Santorini with BBQ, Drinks and Transfer - Pickup from your hotel and the ride to port
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Sailing Catamaran Cruise in Santorini with BBQ, Drinks and Transfer

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

★★★★★★★★★★4.5 · 568 reviews · 5 hours (approx.) · from $96

Review of Santorini’s 5-hour catamaran cruise with hotel transfers, swimming, snorkeling, BBQ lunch, wine, and volcano views.

“Such a fabulous day out, everything was seamless and so relaxing. Great staff, easy return transfers, delicious food and great communication throughout. Definitely recommend for a lovely cruising day on the sea with a few stops for swimming 🙂”

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Santorini Sailing Dream Catcher with BBQ Lunch and Drinks - Red Beach and White Beach from the sea
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Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

4.Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

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

Sail Santorini’s caldera, swim at volcanic hot springs, enjoy a Greek BBQ, and take in Red Beach, White Beach, and sunset views.

“I went soli today and the vibe in the boat is actually amazing where you can start making friends so fast there. The crew members and the food are both amazing. The swim stops are nice as they picked good spots compared to other boats I have been to”

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Santorini Luxury Sailing Catamaran Cruise with BBQ, Drinks and Transfer - The hot springs at Palea Kameni
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Santorini Luxury Sailing Catamaran Cruise with BBQ, Drinks and Transfer

Santorini Caldera Sailing Tour with BBQ Lunch and Drinks - Hotel pickup and the Vlychada departure
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Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

6.Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

★★★★★★★★★★5.0 · 268 reviews · 5 hours (approx.) · from $230

Review of Santorini’s 5-hour caldera catamaran cruise with hotel pickup, swimming stops, BBQ seafood lunch, drinks, and sunset options.

“The thing to do in Santorini. Was a bit long and spent the majority of the time on the boat. Could have easily been a 3 hour activity. Stopped to swim 2 times and was only given a rushed 10-15 minutes to swim and spent the rest of the time on the boat. Didn't stop to get off at any beaches. Nice crew. They have medicine for motion sickness on board which was very helpful.”

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Santorini Small-Group Catamaran Sailing Trip(BBQ,drinks, transfer) - Sailing Around the Caldera
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Santorini Small-Group Catamaran Sailing Trip(BBQ,drinks, transfer)

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

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

Review of Santorini’s small-group catamaran cruise with hotel transfers, swimming, hot springs, Greek BBQ, drinks, and sunset views.

“We had the most AMAZING time on this Sailing trip. It was the highlight of our 8 days spent in Greece. The captain - Alex and the crew - Rafaela and Aneoyis were great. The stunning views of the coast line gave you a completely different perspective than the view from land. We did the afternoon/sunset tour which we would highly recommend. This was such a memorable experience. Thank you!!”

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Santorini Caldera Sunset Sailing Cruise with Dinner and Wine - Starting at Santorini’s Old Port
Boat Trips in Santorini, Cruises & Boat Tours, Dining Experiences, Dining Experiences in Santorini, Dinner Experiences, Evening Experiences, Sailing, Sailing Trips, Sailing Trips in Santorini, Santorini Caldera & Volcano Cruises, Santorini Tours, Sunset Cruises, Sunset Cruises in Santorini, Tour Reviews, Wine Tours, Wine Tours in Santorini

Santorini Caldera Sunset Sailing Cruise with Dinner and Wine

8.Santorini Caldera Sunset Sailing Cruise with Dinner and Wine

★★★★★★★★★★4.5 · 208 reviews · 6 hours (approx.) · from $97

Review the Santorini sunset sailing cruise with volcano hike, hot springs, Greek dinner, wine, practical tips, and honest value advice.

“We were looking for an excursion that would let us experience Santorini without all of the crowds and this was a great choice. We had a lovely afternoon getting to see the beauty of the surrounding island, the hike to the volcano and the swim in the hot springs was so fun. The crew was fantastic and the food was delicious. The sunset was beautiful. I would highly recommend that anyone spend an afternoon on this tour.”

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Santorini Sunset Sailing Cruise: Dinner, BBQ, Open Bar, Transfers - Red Beach gives the cruise an early visual jolt
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Santorini Sunset Sailing Cruise: Dinner, BBQ, Open Bar, Transfers

Santorini Private Sunset Sailing Tour with Dinner, Drinks &Transfer included - Passing Santorini’s famous Red Beach
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Santorini Private Sunset Sailing Tour with Dinner, Drinks &Transfer included

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

★★★★★★★★★★5.0 · 145 reviews · 5 hours (approx.) · from $651

Review of Santorini’s private sunset sailing tour, with Red Beach, Thirassia, dinner, open bar, swimming, and hotel transfers.

“Best day EVER here on our trip to Santorini, Greece! George and Elias gave us the VERY BEST sailing experience. It was a dream come true and a day to remember. We did the personal tour and they made us an authentic home cooked Greek Dinner that was one of the best Greek meals we ever had! We highly recommend this cruise! The views we put our eyes on were like heaven! George, if you are reading this… Thank you! Thank you! Thank you!! You made one of my bucket list items come true! Bill and I love you to pieces.. Elias too!!”

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Private Motor Yacht Cruise with BBQ, Open Bar & Transfers - Getting to Vlihada Marina
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Private Motor Yacht Cruise with BBQ, Open Bar & Transfers

11.Private Motor Yacht Cruise with BBQ, Open Bar & Transfers

★★★★★★★★★★5.0 · 144 reviews · 5 hours (approx.) · from $1,149

Review of Santorini’s private yacht cruise with BBQ, open bar, swimming, hot springs, hotel transfers, and sunset views.

“My wife and I could not have been happier with this experience. The weather was a little rough in the morning which created some waves but the crew assured us there was no danger. We had a fun ride out along the coast and then enjoyed the hot springs and some snorkeling! This was followed up by a great dinner and incredible view of the sunset. From start to finish the crew was attentive, informative, and really fun! It was definitely worth the cost! 10/10!!”

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Deluxe Santorini Sailing with BBQ and Drinks Shared Tour - Red Beach and White Beach from the sea
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Deluxe Santorini Sailing with BBQ and Drinks Shared Tour

12.Deluxe Santorini Sailing with BBQ and Drinks Shared Tour

★★★★★★★★★★5.0 · 137 reviews · 5 hours (approx.) · from $194

Review of Santorini’s 5-hour shared sailing tour with BBQ, drinks, swimming stops, hotel transfers, and sunset or daytime options.

“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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Sunset Caldera Sailing Cruise - Starting at Vlychada Marina
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Sunset Caldera Sailing Cruise

13.Sunset Caldera Sailing Cruise

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

Review the Santorini Sunset Caldera Sailing Cruise, with a 10-person boat, Greek meal, drinks, swimming stops, and hotel pickup.

“What we liked about this cruise is that there were only 10 people allowed on a tour, we like small number of people. The food was yummy, and the staffs were really nice and knowledgable about the area which we enjoyed learning about Santorini. We highly recommend this tour.”

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Santorini Private Daytime Sailing Cruise with Meal, Drinks &Transfer included - Starting at Vlychada at 10:00 a.m.
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Santorini Private Daytime Sailing Cruise with Meal, Drinks &Transfer included

Santorini Caldera: Sunset Sailing Cruise with Meal - Red Beach and White Beach From the Water
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Santorini Caldera: Sunset Sailing Cruise with Meal

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