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5 Greek Islands That Few People Know – Discover Them on a Sailing Boat!

Greece may have made the headlines for all the wrong reasons in these recent years, with an economy still struggling to pull through what was probably its most troubled period in modern history. However, the seas are as resplendent as ever and its beaches, taverns and traditions can still charm anyone who sails to their coast. While chartering a sailing boat in Greece is the smoothest bit of work you will have to do, choosing which spots to visit may be overwhelming. With over 200 inhabited islands, narrowing your search down to a handful can take quite a toll on the planning of your yachting holiday in Greece. More so if you decide to skip the more touristic options and go for the quaint and less busy of the islands. This is why we have laid down the groundwork for you and selected our top five “secret” islands to discover on your very own, chartered sailing boat.

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Kastellorizo island and undiscovered gem of Greece

Source: Conde Nast Traveller

Its remote position as part of the Dodecanese archipelago in the south-east has given this island it’s own mood and setting, removed and yet still very much a part of, the traditional Greek atmosphere. As soon as your sailing boat enters its sweeping harbour, you will realise this is a sleepy island, soothed by the sea which brought both danger and wealth to its shores. Find peace in its tranquillity and relish in the mix of influences from Greece, Turkey, France, Italy and even Britain.


the relatively unknown Milos island of Greece

Source: YouTube

Milos is aptly known as the island of colours for good reason; the strange geological formations aided by volcanic activity in the area, its 70 brilliant beaches with colours to rival azure gems and the pretty syrmata houses cover the island in a resplendent blanket of a million hues. Follow the colourful bougainvillaea as it snakes its way up the golden stone of the buildings on Plaka, one of the largest towns perched on the mountainside, and a smaller version of Olympus if we ever saw one. Take this all in as your boat sways gently in the harbour and enjoy some of the most beautiful sunsets in the world.

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Hydra island  in  Greece

Source: Mysterious Greece

Perhaps more up-market than the rest in this list, Hydra lacks the beauty of some of Greece’s most noteworthy beaches but offers much in return. You cannot hope to ferry your vehicle across – residents and visitors get around by mules and there’s a ban on construction projects, leaving the city in a fixed, timeless era which visitors immediately come to love. Its stunning rocky shores can only be reached by boat, making it the perfect, tranquil haven for your yachting trip. Visit the island in late June for the Miaoulia, a traditional festival celebrating Greek naval victories with fireworks in the picturesque harbour.


boats waiting in Alonissos island in Greece


Found at the very centre of a National Marine Park, Alonissos is the perfect sailing destination for the opportunity it offers to fish and spot the protected Mediterranean monk seal. Forget the white-washed buildings and rugged terrain on Greek postcards. At Alonissos, you can immerse yourself in dense woodlands, follow the less beaten track and enjoy the stunning views this island allows you to glimpse between one pine tree and another.


boats docked in mystical island of Symi in Greece


Enjoy the true Mediterranean lifestyle in Symi, a tiny island also part of the Dodecanese archipelago just off the Turkish coast. Its colourful houses stand boldly against the green mountainous backdrop and the smell wafting from taverns of freshly caught fish will truly put you in the quintessential Greek mood. As your sailing boat makes its way to Symi’s amphitheatrical port (a national monument in itself), bathe in the island’s simple beauty and let your senses enjoy every second of this destination.

Greece offers more than meets the eye: a small detour on your boating trip will take you past coastlines which seem to jump straight out of a mythical tale and every rocky bend is a rich discovery. Charter a sailing boat with Book2Sail and discover Greece’s best-kept secrets.

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