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  • Writer's pictureMyra

Easy Sailing for Beginners: Greek Islands

Updated: Mar 17, 2020

Hello summer lovers!

I know, I know, as I write this, it’s February, and it’s cold, dark, and wet outside. If you’re a summer person like me, maybe you’re already counting down the weeks to beach o’clock, and warm nights under the stars. You might think of the Mediterranean blue waves and the shining white houses of the Cycladic Islands, hot sand in the afternoon and a welcome breeze in the early evening. Maybe you scroll through Instagram, and wonder why these tantalizing photographs seem so far away.

“This is about how to have a sailing holiday without knowing how to sail.”

Setting up a sailing trip is easier than you think

That’s it, you think, I want a vacation. Where should we go? Then maybe you consider one or two islands, whatever you can squeeze into your week off. Then you see a sailing yacht and say, what if we could skip the hotels and ferries, and see lots of islands? Yacht sailors get to do that. Why can’t we do that?

Good news, you can, and you don’t need to be a sailor to enjoy all the perks of a sailing yacht vacation. Even better news, setting up a sailing trip is easier than you think. I’m here to share a few easy steps, but not on how to sail. This is about how to have a sailing holiday without knowing how to sail.

girls on sailing yacht
Look, no hands!

Step 1: Where should we go?

You think the Cyclades sound great, or maybe the Saronic Islands. How do you get there? Luckily, all you need to do land at Athens International Airport, and there are bases located a short drive away on the southern part of the Attica peninsula.

sailing route for Kythnos, Serifor and Sifnos

Pro Tip: From Lavrio Base, Kea is a short 2 hours away and so the island hopping begins. Also close by are Kythnos, Serifos and Sifnos, Andros and Tinos… Visit not only the islands, but also access by boat their extensive coastlines – that’s the main idea, right?

Step 2: When can we sail?

Well, when do you want to go? There are plenty of yachts available in the sailing weeks from April until October, and variations to suit every budget (bigger yacht sizes and high season weeks increase charter fees).

Pro Tip: The sea stays warm well into October. A sailing & swimming holiday is also wonderful in April and May, when the sun is pleasant and there are fewer tourists on the islands.

Step 3: I don’t know how to choose a yacht.


You don’t need to know everything about yachts, relax. Choose a yacht for fun. How many are in your group, and what would you like to do? Do make sure the yacht you book offers comfort, such as air conditioning, a dinghy with an outboard (handy to reach beaches), and offers fun, such as sea toys and wi-fi.

Step 4: Wait, we can’t sail this thing!

No problem, you get a friendly skipper with in-depth knowledge to help you map out your journey around the Greek Islands, keep in mind the weather during the charter, what kind of activities you want to do, how long you want to sail every day, and so on.

The skippers also know how to get mooring spaces at each island and all the hidden bays that allow for fabulous swimming and snorkeling in quiet, crystal blue waters. They know the good restaurants and worthwhile sites to visit, and speak English and other languages.

Pro Tip: If it's windy and uncomfortable in one direction, use the biggest advantage of your charter yacht and ask the skipper to suggest the best alternatives. There are countless bays, beaches, villages and ports to visit and the skipper knows most of them.

Step 5: Food & activities - is sailing really better than a hotel vacation?

Oh, yeah. Dine privately on board anytime you want. No busy buffets and eat the food you like. Also, there is no ‘forgetting’ anything back in the room, or paying to hire a car. The yacht has all your stuff and takes you places a rental car cannot. You get quiet bays with beautiful clean water, so no fighting for an umbrella at the beach or pool.

Sailing yachts in crystal blue green waters in Greece
Kleftiko: Access by boat only

Pro Tip: Friendly charter operators (the guys giving you the boat and skipper) discuss your wishes and fit what you want to best suit the sea conditions. It always depends on the weather and what kind of journey you would like – more sailing time or more exploration of bays and islands? Do you have children or other sensitive passengers to consider? They advise the better wind and sailing directions for your specific charter week, and help you set up an itinerary customized for you.

Step 6: Is there anything else to do except snorkel and sail?

Yes, plenty. Besides exploring island destinations, enhance your sailing holiday with on board wellness such as yoga, massage or fitness training, or add specific cycling, hiking and swimming routes to keep you active.

Pro Tip: You’re not just ‘renting’ a boat. Before the trip, get all the shortcuts you need to set up a journey of a lifetime. Get a yacht from operators that take the time to advise you, calmly set up extra services, and care enough to make your sailing vacation in Greece the best one yet.


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