Sailing holidays in Greece

The Cyclades archipelago sits to the southeast of the Greek mainland, within easy access of Athens, and boasts a really varied sailing itinerary between more than 200 islands. The larger, inhabited islands of Santorini, Mykonos and Naxos usually stand out as popular highlights, sailing to Sifnos, Syros and around some of the Lesser Cyclades is also hugely rewarding. On the other side of mainland Greece, you’ll find the Ionian Islands – there are fewer than there are Cyclades, but they are greener and lusher. They include Corfu, Lefkada, Ithaca and Kefalonia – and, in the summer, they are a popular playground for gentle sailing.

Over the course of one or two weeks it’s possible to sail for approximately four hours between islands before anchoring either at the main harbour or at a secluded cove or surrounded by literally nothing other than water. Itineraries are often not fixed, as the very nature of a sailing holiday means you are dependent on which way the wind blows (and how hard!) – so not knowing where you’ll land each day adds a real sense of adventure to these trips.

Whether you are looking to learn to sail or just enjoy sailing as a means of getting from one aquatically alluring A to an even more beautiful B, sailing holidays in Greece are all about going with the flow.

Hiking and cycling on dry land or simply swimming or snorkelling off the back of the boat, as well as scuba diving, can all feature within a typical itinerary. Your skipper will be able to make alternative suggestions depending on the weather and the wishes of the group. Flexibility is key to a successful sailing holiday in Greece with everything from volcanic calderas and scenic sunset spots to time spent on secluded beaches ensuring you’ll never be left ‘all at sea’.

Combining a sailing trip with additional activities is a great way to break up the day. Scuba diving or yoga are just a couple of pursuits that instantly go hand in hand with a sailing holiday in Greece. There are also opportunities to go cycling on Siphnos, Seriphos and Syros, whilst conservation holidays focus on protecting marine life and come complete with an on-board expert biologist/naturalist. You might also find SUP boards and fishing equipment at your disposal. Basically, whatever you fancy can be arranged although, sometimes, just a good book and a glass of wine is all you need.

Numerous islands in Greece, particularly larger ones like Mykonos, Santorini and Naxos, get really busy during the summer. Cruise ships clog up the main ports and hundreds of backpackers pour out of gigantic ferries. One of the benefits of sailing on a small boat is that you can anchor wherever you choose and sail to bays and beaches that will be completely inaccessible to a much larger vessel. There will be plenty of opportunities to discover traditional Greek culture, too, as you eat at authentic waterfront tavernas, without the need for bulk bookings and English-written menus. Mooring at remote fishing villages offers local people a chance to benefit financially, even though they’re way off the traditional tourist track. And hikes to watch the sunset from a clifftop church or lazy afternoons strolling around whitewashed labyrinths are all the more enjoyable without worrying that you’re going to miss the boat.

Wherever possible crew members, including the skipper, will be Greek so as to offer a more personal account of the history and culture of the islands, as well as ensuring income goes back into local pockets. Passengers looking for a more intimate sailing experience – a honeymoon, perhaps – can tailor make a tour to suit their wishes with a choice of private crewed boat hire.

For the majority of these sailing holidays in Greece, you won’t need any experience of sailing although some trips can be more ‘hands on’ than others. Brushing up on a few knots and sailing terminology is always a good place to start; however, landlubbers are more than welcome with the chance to learn as you sail probably the best way to get the most from the experience.