Santorini Sailing Cruise with Fairwind: A 2025 Review

You know, there are a million pictures of Santorini, and pretty much every single one is stunning. Actually, the real thing is even better. I mean, trying to figure out the best way to see the island can feel a little overwhelming. There are, frankly, a lot of options out there. As a matter of fact, we decided a sailing trip would be the perfect way to get a different point of view of the caldera, so we chose the sunset cruise with Fairwind. Honestly, it turned out to be one of the absolute highlights of our trip. At the end of the day, there’s something about being on the water, looking back at those cliffs, that you just don’t get from standing on the land. We went for the 2025 tour, which, obviously, gave us a look at what they have planned for the coming season.

I mean, this wasn’t just a simple boat ride around the bay. Basically, it felt like a full-day experience squeezed into about five incredibly memorable hours. You get to swim in some truly special spots, eat a meal cooked right on the boat, and, of course, watch that world-famous sunset from what is arguably the best seat in the house. We found that the crew really made the trip special; they were friendly, knew a lot, and obviously loved showing people their beautiful home. In other words, they seemed to genuinely care that everyone was having a good time. Still, the whole setup was pretty much perfect, from the moment we stepped on the boat to the moment we, sadly, had to get off. Anyway, let’s get into the details of how the afternoon actually unfolded.

Setting Sail from Vlychada Marina

So, the day’s adventure kicks off at Vlychada Marina, which is, by the way, a really cool spot on its own. The marina is tucked away and is surrounded by these incredible pumice cliffs that have been carved by the wind and sea over centuries, you know. Actually, they almost look like something out of a sci-fi movie. As a matter of fact, the check-in process with the Fairwind team was incredibly smooth and welcoming. Right from the start, there was a feeling that this was going to be a well-organized and person-focused trip. Okay, so when you first see the catamaran, it’s quite impressive. These boats are really spacious and look absolutely pristine. We found plenty of places to sit, either in the cool, shaded cockpit or out on the open netting at the front if you really want to catch some sun.

Once everyone was on board, the captain, you know, gave a really clear safety briefing and an outline of the day’s plan. Frankly, you could tell he had done this a thousand times, yet his enthusiasm was still very much there. He pointed out different things as we were pulling out of the marina, which, honestly, was a nice touch. I mean, the feeling as the catamaran pulls away from the dock and the sails catch the wind for the first time is pretty much pure bliss. The gentle rocking of the boat and the salty air immediately put you into a holiday state of mind. Anyway, with the white-washed villages of Santorini shrinking in the distance and the deep blue of the Aegean ahead, it was kind of hard not to have a huge smile on your face. You get unlimited soft drinks, local white wine, and beer right from the start, which, of course, is a very nice way to begin.

First Stops: The Colorful Red and White Beaches

Alright, so our first real destinations were two of Santorini’s most well-known beaches, which, by the way, are almost impossible to truly appreciate from the shore alone. First, we sailed past the Red Beach. As a matter of fact, the sight of the towering, rust-colored cliffs crumbling down to the dark volcanic sand is literally breathtaking. The color contrast with the turquoise water is something a photo just can’t completely capture. The captain, you know, took us in pretty close, so everyone could get some amazing pictures. Then, it was time for the first swim stop, which was just off the neighboring White Beach. Honestly, getting to dive straight from the boat into that crystal-clear, refreshing water was an absolute dream. It was just the perfect temperature, not too cold at all.

You know, the crew provides everyone with noodles and snorkeling gear if you want it. Seriously, I’d really recommend grabbing a mask and snorkel. Just below the surface, the underwater world is kind of quiet and beautiful, with some interesting rock formations to see. It’s obviously not the Great Barrier Reef, but floating around in the Aegean, looking at the fish and then up at the huge white cliffs, is more or less a perfect moment. I mean, we spent a good amount of time here, so it never felt rushed. You could just swim, float, or even stay on the boat and sip a cold drink if that was your preference. At the end of the day, the freedom to just enjoy the moment was one of the best parts.

A Taste of Greece: The Onboard Barbecue

Now, while we were all swimming and enjoying the water, something really amazing was happening back on the catamaran. I mean, the crew was busy preparing a full-blown Greek barbecue. Seriously, the smells coming from the back of the boat were absolutely mouth-watering and definitely got everyone’s appetites going. By the way, this wasn’t just a few sad-looking burgers on a grill. This was a proper feast. Once everyone was back on board and dried off, it was time to eat, and honestly, the spread was very impressive. We’re talking about delicious grilled pork skewers, chicken, and some incredible local sausages, all cooked to perfection right there on the boat.

To be honest, the food alone would have been worth the price of the ticket. I mean, everything was so fresh and full of flavor. The fact that you’re eating this amazing meal while anchored in a beautiful cove in Santorini is, frankly, just surreal.

In addition to the grilled meats, you know, there was a whole array of side dishes. For example, there were fresh Greek salads, a really tasty shrimp dish in a tomato sauce, dolmades (stuffed vine leaves), and plenty of fresh bread. Of course, the local wine was still flowing freely. Eating this amazing food, with the sun on your skin and a gentle sea breeze, while chatting with fellow travelers from around the world, was just a little bit magical. Basically, it felt less like a tour and more like a great party with new friends. At the end of the day, the meal was a genuine highlight and showed a real commitment to giving guests a high-quality experience.

Volcanic Hot Springs and Caldera Views

Okay, so with our stomachs full and feeling very happy, the next part of our trip took us right into the heart of the volcano. The boat sailed towards Palea Kameni, one of the two small islands in the center of the caldera formed by volcanic eruptions. Anyway, this is where the famous hot springs are. The captain anchors the boat a little way from the springs, and you have the option to swim over to them. As a matter of fact, it’s a bit of a swim, so you need to be a reasonably confident swimmer to do it. The water changes color here, you know, getting a kind of rusty, orange-brown hue from the sulfur in the springs. The crew warns you that the sulfur can stain light-colored swimwear, which is definitely something to keep in mind.

Once you reach the shallow inlet, the water is, frankly, much warmer, almost like a hot bath. I mean, it’s a really strange and cool feeling. People were covering themselves in the mineral-rich mud, which is supposed to be good for your skin. Whether that’s true or not, who knows, but it was just really fun. After a good soak in the thermal waters, you swim back to the catamaran, which is, obviously, a bit cooler but incredibly refreshing. Now, the boat starts sailing along the edge of the caldera cliffs. This part of the trip is just visually stunning. You get to see the towns of Fira, Firostefani, and Imerovigli clinging to the very top of the cliffs, looking like a dusting of sugar. Frankly, seeing them from this perspective, from sea level looking up, really gives you an appreciation for the sheer scale and drama of the island’s geography.

The Main Event: Sunset Below Oia

Finally, we reached the moment everyone was waiting for. To be honest, it’s the reason many people book this specific cruise. The captain skillfully positions the catamaran in the perfect spot just below the iconic village of Oia. From here, you get a completely unobstructed view of the sun as it begins its slow dip into the Aegean Sea. As a matter of fact, the crew turns off the music, and a sort of respectful quiet falls over the boat. Everyone just finds a comfortable spot, grabs a drink, and gets their camera ready. Honestly, watching the sky change color is a spectacle in itself. It shifts from a bright, brilliant blue to soft shades of orange, then pink, and finally, a deep, fiery red.

I mean, seeing the light catch the white buildings of Oia, making them glow, is just beautiful. Then, you see the sun, a perfect fiery orb, touch the horizon and slowly disappear. It’s a very emotional and moving sight, and being on the water, away from all the crowds jostling for a view in Oia, makes it feel incredibly personal and special. There’s a sort of shared magic in that moment, as everyone on the boat watches in silence. After the sun finally vanishes, you can actually see the lights of Oia begin to twinkle on the clifftop. Basically, it’s the picture-perfect ending to a truly amazing day on the water, a memory that you will definitely not forget anytime soon.

Read our full review: Sailing Cruise Santorini Fairwind Review Full Review and Details

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