How to plan a dream private yacht sailing trip around the Greek Islands 

At the end of last summer, I found myself torn. I had a week booked on the Greek Island of Corfu with my best friends from school, which clashed with a work opportunity to sail around the Portuguese Azores islands on a private yacht charter – while the latter was a dream trip for me, time with my friends was always going to be the winner. Happily, we spent the week drinking Ouzo, visiting picturesque beaches, munching on Feta and laughing constantly. In summary, it was a dream trip of its own!

But, it got me thinking, how awesome would it be to go island hopping with my best friends and explore more of the country? One of my friends is an ex croupier on a cruise sheep, my other a chief steward on a luxury yacht, so although it seemed we had some of the skills needed to embark on such an adventure, my research on Click and Boat quickly taught me that if you didn’t want to learn to sail but still wanted to charter your own yacht, there were many options with a skipper included. The bonus as well was the prices weren’t quite as heart-wrenching as you would expect.

So, quickly, it became another dream of ours to start planning an island hopping adventure together, looking into yacht charters in Greece because we all love the Greek islands. Still, to be honest, we are all slightly restless souls that like to explore as much as possible on holiday. Even when I packed myself off to Kos the year before for my ‘sun, sand and nothing else’ beach holiday, I ended up hopping on some island trips to nearby islands like Nisyros, one of my favourite islands in the world. There are so many beautiful smaller islands across Greece that the appeal of setting sail and exploring by boat is undeniable.

The city of Athens with the monuments rising high above atop the green hill

Explore the capital of Greece, Athens, before setting sail

Why a private yacht charter appeals to me?

There are other reasons that a private sailing trip appealed to me, though. Firstly, I’m trying to reduce the amount of flying I do, as while much of my job is tied to flying, it’s the elephant in the room everyone in this industry needs to acknowledge. With solar panels starting to appear on boats, and entirely wind-powered operations, sailing is undoubtedly kinder to the environment than taking multiple flights to hop around Greece, often involving connecting flights in key-hubs.

Secondly, while the idea of a cruise had once appealed to me, and I’ll admit I did enjoy my cruise around the Baltic Sea a few years back, I liked that because it was lots of little city-breaks tied together, visiting the likes of St Petersburg without needing a visa, or having a day exploring Tallinn works in my mind, when I want an island holiday, I want to relax and go at a slower pace, not defined by an 8-hour limit on ports. Also, as it turned out, cruising isn’t exactly great for the environment.

More recently, of course, Coronavirus has exposed some of the downfalls of having 5000 people together on a ship, eating together, confined together – and the idea of being in quarantine on a mega-ship makes me shudder, so small, private, Greek yacht charters also navigate that option.



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