Let Your Dreams Set Sail in Santorini!

When sailing the seas around Santorini, there are an overwhelming number of options. I can assure you that I have researched all options, and experienced a few firsthand, but I am writing about only the absolute BEST experience.

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When I began researching, I found two types of trips to be most prominent – a packed tour cruise or a party boat cruise. The volcano (tour) cruises offer the most cost effective means to experience a large, traditional, wooden boat (although they are packed – shoulder to shoulder – with tourists). These options make their way through the mouth of the caldera for a tour of the volcano and the nearby hot springs. The party boat cruises are typically done on a catamaran with more of a focus on boozing round-the-island, swimming and snorkeling (nothing wrong with that!).

But what if you want it ALL? I certainly did. My ideal sailing experience seemed out of reach as I continued to research… unless we splurged on a private boat with a custom schedule.

What was included in the sail of my dreams? Oh… you know, just ALL of the following activities wrapped up into one, affordable package…

1. Large, traditional boat (gotta have the authentic experience!), but one that is not packed with tourists. I need room to ride the winds freely!

2. Tour of the volcano – but no more than an hour of trekking around on hot, lava rocks – with a knowledgeable guide to lead the way.

3. Wine, booze and tunes. Hey, I’m not all business!

4. Traditional Greek food served to my hunger’s content.

5. Jumping, swimming, and exploring the famous Santorini Hot Springs!

6. Sunset accompanied by wine and live music.

Is my ‘modest’ request too much to ask? Apparently not, thanks to the rare, semi-private sailing adventure that Sailing Santorini Cruises provides! 

We arrived at the old port of Fira in the afternoon to be greeted by Nadia, our lovely host for the day. I wasn’t quite sure what to expect on a ‘semi-private’ cruise (I typically make a beeline in the opposite direction of tourist traffic jams). For those who want to splurge a bit, or have a larger group, Sailing Santorini Cruises also offers private sails on their large ships, but the semi-private option seemed the best fit for our group of three.

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I can’t accurately describe the excitement I felt when the bold and beautiful, Thalassa, my sailing savoir, pulled up to port! No more than thirty people boarded the large boat, fit for well over a hundred, with plenty of places to lounge and even a cocktail bar located mid-ship.

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Our first stop was the islet of Nea Kameni – the ACTIVE volcano of Santorini – which is the youngest in the Eastern Mediterranean, with the oldest rock formations dating back 430 years and the youngest only 50. That’s right – this volcano’s last eruption was a mere 50 years ago! The natural beautify of the volcanic center was truly incredible!

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We walked for about 45 minutes, exploring the gorgeous formations and experiencing smoking pockets where you could feel heat rising from the rock’s surface, escaping from lava deep below. Nadia is an expert on the history of the volcano, and provided interesting details about the various eruptions and how they have shaped the surrounding islands.

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Next we sailed to hot springs, where we flipped from the side of the boat (but of course!) and swam towards a small white chapel built atop black, volcanic rocks emerging from the sea. The water was not ‘hot’… not even close, but there was indeed a nice, muddy warmth that provided a welcome contrast to the cold waters surrounding – proof of the active volcano below!

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We were told that mud from the springs contains minerals good for your skin. Many joked that this was simply a trick played on tourists to make us all look silly. Silly you say? We look totally badass, right? Personally, I found the mud refreshing and can promise that playing in it is loads of fun!

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After our hot-spring swim, we sailed close to the docks of Thirassia, the second largest of the complex of islands formed by volcanic eruptions. It was at this time in the cruise my mind was truly blown. Everything up to this point was somewhat expected. What I did not expect was an overwhelmingly delicious meal! We have had our fair share of spanikopita, meatballs, sausage, dolmas, tzatziki and fava beans on this trip, but the traditonal Greek meal served aboard the Thalassa was by far one of the best! This was a highly unexpected treat!


We washed our meal down with Santorini white wine, and were even given blankets when it started to get a bit chilly. Every detail for ultimate comfort was provided.

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Our final treat on the five hour tour was a cozy, breezy sail to the northern tip of the island for a seaside view of beautiful Oia.

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At this point the crew raised the main sails and we slowly rode the winds, serenaded by live saxophone music at sunset… pinch me.

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This was truly a magical experience! Thanks to an amazing crew, and especially to our incredible host, Nadia, for a day we will dream about often.


I’ts not far to never-never land, no reason to pretend. And if the wind is right you can find the joy of innocence again…

– Christopher Cross


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