SANTORINI
The best of the caldera and beyond.
The 15 most popular sailing cruises in Santorini, in one place. What each trip includes, how long it takes, what it costs and who runs it.
Sail a Santorini catamaran with BBQ lunch, unlimited drinks, and hot-springs swims—plus Red and White Beach views in just 5 hours.
Most Popular“Best part of our trip!! Would highly recommend! Perfect way to spend a day sailing around the island!”
A 5-hour Santorini catamaran with caldera views, swimming stops, snorkeling gear, and a BBQ seafood lunch with unlimited drinks.
“Amazing. Pepe was knowledgeable and a very good cook. Nancy was equally amazing. He guided us through rough waters and made us feel safe. They had to provide us with a piece of nausea gum for which we are thankful!!!”
Santorini catamaran with hotel pickup, BBQ and drinks, snorkel stops at Red/White Beaches, plus hot-springs swim and lighthouse views.
“My husband and I had the best time on our sunset cruise! The crew was awesome and very informative. And the meal we had while on board was delicious! Would definitely recommend!”
Sunset sailing from Vlychada with Red Beach, volcano hot springs, Greek BBQ dinner and open bar, plus hotel transfers in ~5 hours.
“Une expérience fabuleuse merci à l'équipage tout était parfait.la nourriture aussi .Le transfert aussi”
Santorini caldera sunset sailing with volcano hike, hot-springs swim, Greek buffet dinner, and complimentary wine. Pickup options available.
“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!”
Private Santorini sunset sailing with dinner, unlimited drinks, hotel transfers, and swimming near volcanoes and Thirassia.
“George is so friendly, knowledgeable and kind - he really made this tour such a great experience for us. The boat is very comfortable and the swimming spot we went to was amazing! Such beautiful water and so many fish. Highly recommend.”
Small-group Santorini sunset sailing from Vlychada, past Red and White Beaches to Palea Kameni and Akrotiri Lighthouse, with lunch.
“Excellent experience for the great meal to the music attitude and of course the view! The smaller mono hull sailboat and 10 guest limit was perfect for our family. A must do while in Santorini.”
Private Santorini daytime yacht cruise with hotel pickup, homemade meal, drinks, and swimming in Thirasia’s bay plus volcanic caldera views.
“Amazing experience!!! We had so much fun out there had food and watched the fireworks. I highly recommended booking this trip!”
5-hour Santorini caldera sunset sailing with transfers, Red and White Beach, swims, BBQ seafood dinner, and wine.
“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!”
Sail the Santorini Caldera on the Dream Catcher for 5 hours with hot springs, swim/snorkel stops, and a BBQ lunch with drinks included.
“Excellent way of seeing the island from the sea. Exceptional service and friendly staff. Had a great swim and tasty food. A real must for someone visiting Santorini.”
A 5-hour morning sail from Vlychada with caldera views, multiple swims, snorkeling gear, volcanic hot springs, and a seafood BBQ.
“Amazing experience. Started off with being picked up from our hotel (which we were messaged the day before, with pick up times) which was great. We were warmly welcomed onto the boat by Chris the captain and Marieangela. The boat is lovely and clean with plenty of space for us to either sit at the…”
Private 44ft sailing with George on Santorini: Red & White Beach photos, volcano views, Thirasia swim, homemade meal, unlimited drinks, transfer included.
“I took a solo sailing trip with George at Angel Sailing and it was an incredible experience! Not only did he show me some of the amazing sights, islands, and historical facts about Santorini, but his hospitality was also exceptional. He provided grRead more”
A 5-hour Santorini morning sailing with Red and White Beach photo stops, volcanic swim time, and a seafood BBQ with wine.
“Barca Sailing was the absolute best!”
Sail Santorini by catamaran with hotel pickup, snorkeling gear, lunch, hot springs, and a sunset finish from Fairwind.
“The crew members are extremely nice and professional. We loved the trip the best! We will recommend our friends for their future trip.”
Private Santorini caldera sailing with open bar, lunch or dinner, snorkeling gear, and a geothermal hot-spring swim near the volcano.
“Our sailing trip with Konstantine and Nicholas was delightful. They really showed up an excellent time! And the lunch was delicious — especially those shrimp and mussels!”
Every village on the caldera rim, and every way out onto the water.
