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Bareboat Charter Cyclades

Sail the Cyclades Islands


The Island Sailing team combines unrivalled experience with specialist expertise in every area of yachting to provide a first-class, personalised service. We offer support and advice to all our bareboat customers. The Cylades base teams are on hand from the start of your charter and will be waiting to catch your lines at the end.

The Cyclades

The Cyclades Islands are popular sailing areas not just for their proximity to Athens. The western Cyclades islands include Kea, Kithnos, Serifos, Sifnos and Milos and most resemble what people picture Greece to look like. The islands transport you to a beautiful world of white washed houses, cobalt blue, stunning turquoise waters and blue sky. Further afield the remaining islands including Paros, Naxos, Mykonos, Ios and Santorini complete a magical island chain with plenty to see and do, from bustling cosmopolitan towns to sleepy picturesque fishing villages.

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What is it like to sail in the Cyclades?

Stretching out south of Athens this vast group of islands is a great sailing area for enthusiastic crew and an experienced skipper. A more challenging sailing area than most with strong summer meltemi wind blowing up to Force 8+, sometimes for a few days at a time. With it’s open seas, it’s only for dedicated sailors in peak summer months but more tranquil earlier and later in the season for a little more relaxation. With so many islands it’s not an easy choice when it comes to where to explore next, especially on a one week charter.

What is the weather like?

The Greek islands in the Aegean enjoy a Mediterranean climate with long, warm summers where the sun shines for over 3000 hours a year! Enjoy fantastic summer sailing holiday weather from May until the end of September when you can expect long, sunny days. During summer the weather in the Greek islands is consistently warm both day and night. In spring and autumn it is still warm during the day and a little cooler at night but always pleasant. Seasonal winds keep air fresh making the islands in the Aegean great for sailing.

Finding your way around the Cyclades Islands

Navigating the large group of Cyclades islands, many of which have fairly large distances between them can be more tricky. Good passage planning and making the most of electronic and manual navigation equipment is key. You’ll need to be aware of the commercial shipping heading to Piraeus and the Corinth canal, as well as fast ferries and hydrofoils serving most of the islands, but the further afield you explore the more tranquil the sailing becomes. We can suggest route plans and itineraries and let you know about all of our favourite spots.

The Cyclades Yachts

Brilliant Boats & Cool Catamarans

Find your Perfect Yacht

We have the widest choice of thoughtfully selected modern yachts built by renowned yacht makers including Beneteau, Bavaria, Jeanneau, Dufour and Hanse and catamarans from Lagoon, Fountaine Pajot and Bali.


We know from experience what specifications and options make for a great charter yacht. There’s a choice of classic slab reefed mainsail or in-mast furling, if you prefer bow thrusters, many of the yachts over 40 feet have them. All yachts have wheel steering and most over 38 feet are twin helm. All yachts have a bimini sunshade in the cockpit and remote control electric anchor windlass. Many of the larger yachts and catamarans also have extras like electric winches, additional large fridges, coffee machines, on-deck drinks coolers and even on deck BBQ’s!


Listen to your favourite music onboard your yacht whilst sailing and relaxing both above and below deck with the latest maritime music systems onboard. Use your devices, cameras and video cameras and keep them charged wherever possible with various AUX and USB ports and charging points. Many of the yachts also offer optional onboard wi-fi if you need to stay connected on charter. All of the yachts have the latest colour GPS chartplotters (as well as the paper charts of course!).


All of the modern, latest generation yachts we offer are designed with sunny Mediterranean and Caribbean sailing in mind. That’s why they all have light and airy designs with plenty of opening hatches, port lights and windows to let the fresh summer breezes circulate around your yacht. In addition, many of the yachts have small cabin fans, some also have these in the salon areas too. Many yachts over 47 feet and the majority of catamarans also have air conditioning and a generator.


In addition to your beautiful yacht – the ultimate ‘water toy’; all boats come with a dinghy tender and optional outboard engine for exploring coves and little beaches and getting to shore when anchored in a pretty bay. Almost every yacht offers a modern, wide sunbathing platform and on the larger yachts these are often electrically operated. Most yachts also have additional water toys you can hire, such as stand-up paddle boards (SUP’s) or kayaks.

Ask us Anything

Find out more about Bareboat Yacht Charter in the Cyclades. More than just experts, we have lived, worked, sailed and explored the Greek islands for decades.

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