Top Santorini Sailing Tours - page 4
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What are people saying about Santorini
Allison_H, Jul 2026
A perfect day!
What a perfect day. The boat was spectacular, all of the stops were wonderful and well organized. Our host, Sara was so charming and we fell in love with her. We made some new friends. Ate some magnificent food that was prepared for us by the crew, swam, drank, listen to music and had just a perfect day.
Cindy_H, Jul 2026
Wow!
What an incredible experience on the Anna catamaran! Roomy and comfortable, The crew was top notch, appearing before we had to ask to refill our cups of wine and anticipated our requests! The food was delicious and plentiful! And the views were too die for! Swimming in the Aegean was a cold but awesome experience! And the fellow passengers were friendly and fun to be with! The crew was personable and knowledgeable. A great time was had by all!
Sara_B, Jul 2026
5 star day with the ‘Caldera’ crew!
We had the most amazing morning with the crew on the Caldera! From our driver who picked us up to start our day, to our host Julia, and the chef, captain, and crew-we were treated with top notch, white glove service from start to finish. We booked a private tour for just my husband and I, craving exactly that-privacy. The boat is big, even with a crew of 4, we felt like we were given our space.. but our glasses were never left empty or anything we needed not tended to immediately. Julia was a wonderful guide and gave us so many nice tips and info about the island, she was so lovely and sweet! We even talked about how much we both missed our dogs back home, her kindness always felt authentic. And the food? OMG- easily the best we've had in Greece (no but seriously, my husband said the shrimp was the best he's had yet on this trip.. and we've traveled Greece for the last 2 weeks). They were super accommodating to my dietary needs (vegan), and there was so much food... we left stuffed! The dolmas and grilled eggplant,
10/10! All the stops we made were lovely, with plenty of swimming and photo ops! The boat was beautiful, new, modern, and comfortable-we couldn't have asked for more. 5 hours of sailing felt like the perfect amount of time. Thank you crew of Caldera, we can't wait to recommend you to friends, family, and our travel advisors! We hope to see you again soon!
-Sara and Don Cowan
Brian_T, Jul 2026
Great Experience. Highly recommend
Had a great experience with my girlfriend and would highly recommend. My only recommendation would be cautioned that the sulfur during the first swim will stain and ruin your cloths and the music was uncomfortably loud on the return but was only for a brief time. Other than that the whole experience was amazing and we absolutely enjoyed the experience from pickup to drop off and would highly recommend it to any one traveling to Santorini.
Mimi_G, Jul 2026
Amazing Experience with Konstantinos!
We had a great time on our sunset Santorini caldera cruise! The guided tour to the volcano was incredibly informative, and swimming in the hot springs was such a unique experience. Our guide, Konstantinos, was excellent and provided fantastic information throughout the whole cruise.He was exceptionally friendly and went above and beyond to make the trip special, even playing some music and singing for us during the sunset. It made the entire experience so much more enjoyable. Highly recommend!
Tylo_R, Jul 2026
100% Recommendable!
This was, without a doubt, the absolute highlight of our Santorini trip! From the moment we booked until we were dropped off afterwards, everything was perfectly organised. The pickup, transfer to the catamaran, and communication throughout the entire experience were seamless and made everything completely stress-free.
The cruise itself was simply breathtaking. The views were absolutely spectacular, the atmosphere was fun and relaxing. It's a memory that we'll treasure for years to come.
A huge thank you to the incredible crew! They were warm, friendly, professional, and genuinely passionate about making sure everyone had an amazing time. They went above and beyond by offering to take photos, answering questions, and making each guest feel welcome and looked after. Another shout-out for the incredible food served during the cruise!
Swimming in the crystal-clear blue waters was definitely one of the highlights and is an absolute must! The crew also provided goggles and floating noodles, making the swimming stops even more enjoyable.
If you're visiting Santorini, don't hesitate to book this experience. It was worth every cent and exceeded all of our expectations. We couldn't recommend it more highly!
Jacqueline_S, Jun 2026
Catamaran Cruise
Great way to see the different island formations. The crew was fabulous — knowledgeable and funny, but always put safety first. Delicious meal on board also. They provide blankets for the latter part of the cruise as watching the sunset can get chilly on the water. Definitely recommend.
Jacqueline_H, Jun 2026
Amazing day!!
Went on the Amorgas today. Alex always our captain and the crew was Silia, Kostas, and Konstantinos. Of the week I spent solo in Greece, this was my favorite.
The tour is extremely organized…taking you from your hotel directly to the boat. Safety is a top priority and a close second is an enjoyable and informative experience.
The music was great…the lunch was absolutely delicious, and the stops were all just the right amount of time. I met amazing people and had the best day.
I can’t recommend the tour enough.
Fernando_V, May 2026
Family hike Fira to Oia
Arsenios our guide was great. With a family of 6, from young to middle aged he kept a good pace engaged in interesting conversations for all of us and was knowledgeable of the ins and outs of history, landscape and picture taking. Definitely recommend.
Danielle_G, Nov 2025
Unforgettable Fishing Trip with Pirate Captain Makis!
Our fishing trip in Santorini with Pirate Captain Makis and first mate Elias was one of the absolute highlights of our entire vacation! From the moment we stepped on board, Captain Makis made us feel welcome, safe, and ready for an adventure. They are genuinely nice guys—equal parts knowledgeable fisherman and entertaining “pirate”—and kept the experience relaxed, enjoyable, and full of laughs.
The fishing itself was incredible, but what made the trip truly special was the amazing meal he prepared right on the boat. He cooked the fish my husband caught along with some homemade tomato fritters, and it was honestly one of the best meals we had in Greece. Simple, fresh, and absolutely delicious. Eating a meal you just caught, overlooking the caldera, felt unforgettable.
Captain Makis’ passion for the sea, storytelling, and hospitality shines through every moment of the tour. Whether you’re an experienced angler or trying fishing for the first time, you’ll feel completely taken care of. We left with great memories, beautiful photos, and full hearts.
We can’t recommend this experience highly enough. If you’re visiting Santorini, don’t miss a day out on the water with Pirate Captain Mikos—it was pure magic!
John_G, Oct 2025
Beautiful Rain or Shine
This catamaran cruise was a highlight of our trip. The food was delicious, too. The weather was rainy and it would have been nice to have a text confirmation that we were still on prior to the trip. Also, people should know that you park nearby & must shuttle down to the boat. It was really a very fun experience overall - these are only small tips! Def recommend! Very beautiful experience.
Danna_S, Sep 2025
Sailing and lunch with a side of snorkeling and swimming
From pick up to drop off it was perfect. Constantine and Karina had the best meal made for us of shrimp mussels salad chicken sausage bread the best appetizer bevies and yogurt with sour cherries. The swim/snorkle areas phenomenal. They shared their knowledge along the way. I would highly recommend. We did 10 am trip.
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An ancient eruption blew apart the island of Thira, creating Santorini. Today, towering cliffs mark the edge of a volcanic crater, while islets host a new volcano, hot springs, and more. Boat trips are the only way to reach these islands and Santorini’s famed white beach. Choose to cruise on a catamaran or a traditional wooden ship, snorkel from a private sailboat with an onboard barbecue, or savor an epic island sunset with sparkling wine on deck. The top Santorini sailing trips will put the magic into your Greek vacation—every single time.
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