header cover

The most beautiful (and little-known) islands of Greece

Guide to Greek islands worth seeing at least once in a lifetime

Lulu and Renato, have been sailing in Greece for over 10 years and have compiled their personal list of the most beautiful Aegean islands to inspire your next boating vacation!

Who better to ask about island hopping in Greece than the experts? 

Renato and Lulu have been sailing the Greek islands for over a decade and, fortunately for all of us, they decided to share their favorite islands. 

After thinking back on their experiences, they managed (somehow) to come up with a list of their 10 favorite islands in Greece. We hope these incredible islands will inspire your next sailing adventure!

Lulu, Renato and Greece

Renato, a rally champion, has been sailing for business and pleasure for more than 30 years. Together with Lulu, the couple has been exploring the world for nearly 14 years. After spending 6 years sailing in the Ionian Sea and 5 years in the Aegean, they set their sights on seeing the more than 2,000 Greek islands and report that there are not many left!

Together they also explored parts of Greece by car and went further, traveling to America, Asia, North America and Africa side by side.

 

Among their favorite destinations, Lulu and Renato pointed us to secret destinations in Greece, many of which are lesser-known and rarely found in other guidebooks and lists; if you are interested in learning more about their history, how they found themselves, and what makes them truly curious navigators, you can read our previous article about them.

Vacation highlights in Greece

10 beautiful (lesser-known) Greek islands to put on your travel list

Sifnos (Cyclades Islands)

Sifnos (Cyclades Islands)

Sifnos is one of the many Cycladic islands we love. The white cube-shaped houses topped by blue domes, the deep red bougainvillea hugging towns, and the Meltemi wind.

In Sifnos, you can learn the art of pottery in one of the many workshops scattered around the Livadia pier (the main port), you can climb the long staircase to the island's monastery and its breathtaking view, you can shop in one of Apollonia's beautiful handcrafted jewelry boutiques, or you can discover one of the island's smallest villages-such as Vathi, which looks like something out of a postcard and where it is unforgettable to arrive by boat!

Koufonissi (Cyclades Islands)

Koufonissi (Cyclades Islands)

There are very few islands in Greece (and in the entire Mediterranean) that can compete with this one on all fronts. Koufonissi is as beautiful and pure as the Aegean. Its sea is a constant blue presence that plays with skill and glee, drawing soft beaches of fine sand, tickling the white houses of the small harbor, creating shimmering blue inlets, lagoons that look like swimming pools, caves of porous rock kissing the clear water like we have never seen before.

The perfect Greek island?

It really could be Kato Koufonissi. Kato Koufonissi hangs on a delicate, almost invisible thread that seems ready to snap. The harbor is the only village on the island, and it is small. In typical Cycladic style, you might expect: lime cottages and blue flowered balconies. But that's not all. Koufonissi has something special because its simplicity is almost abstracted from time and place. Take a beach, a few fishing boats, add a few houses in the background and the sea-a deeper turquoise color you can barely imagine. Here is a picture of the perfect fishing village. Here is Koufonissi.

Amorgos (Cyclades Islands)

Amorgos (Cyclades Islands)

Scrolling through the Cyclades on a map, the last one encountered from Piraeus is perhaps the one with which one must be confronted at least once in a lifetime. Amorgos rises dramatically from the depths of the Aegean and stretches like a lone dragon for more than 30 kilometers - blending the best of the culture, architecture, landscapes and beaches of an entire archipelago.

Amorgos is noble and manages to retain its timeless atmosphere even in high season. It is not a wild party island, but rather a place of meditation and admiration, where one can walk among well-marked paths and swim in beaches that borrow colors from the sky and clouds. The Meltemi wind, which can lash mercilessly in winter, always grants a sheltered shoreline to enjoy its wonderful sea in summer. Despite having such a small population, Amorgos is actually the true heart of Cycladic culture: the sophistication of the beautiful Chora, some incredibly wild and isolated bays, and the incredible Chozoviotissa Monastery. You will never want to leave!

Nisyros (Dodecanese)

Nisyros (Dodecanese)

The active volcano of Nisyros is undoubtedly the heart of the island, offering a unique experience for geology enthusiasts and adventure seekers. The ochre-colored hills surrounding the volcano create a breathtaking backdrop, an enchanting contrast to the deep blue sea.

The wonderful monastery overlooking the sea and the small villages of Nisyros, with their cobblestone streets and whitewashed houses, convey an authentic and enchanting atmosphere. The locals welcome visitors with infinite friendliness, allowing an immersion in local culture and Greek hospitality. You cannot leave Nisyros without sampling the delicious local cuisine, characterized by dishes such as Skordalia (a garlic-potato sauce) and succulent octopus, which you can enjoy in one of the island's traditional restaurants. A must stop is the Aphroditi tavern, renowned for its excellent cuisine and cozy atmosphere.

And for a moment of pure relaxation, Giali's Caribbean lagoon is the perfect place to swim. The crystal-clear, turquoise waters create the perfect setting for the most picturesque swim of your vacation, giving you a postcard-perfect experience and unforgettable memories of Nisyros.

Chalki (Dodecanese)

Chalki (Dodecanese)

Located opposite the beautiful island of Rhodes is a small paradise of beauty and perfection.

The houses of Chalki, painted in delicate pastel colors, create an enchanting image and capture the essence of traditional island life. The balconies of these charming homes overlook the crystal clear sea, providing breathtaking views and a unique sense of peace. One element of great beauty is the village's stunning Church, an icon of typically Greek sacred architecture.

Chalki is a place where time seems to stand still and tranquility reigns supreme. It could be Portofino, but we are talking about Greece and far fewer tourists: the pier where the harbor docks accommodates only ten sailboats!

To make sure you don't miss anything, make a stop at the fishermen's taverns in the small village of Chalki for fresh lobster!

All in all, Chalki is a place where unspoiled beauty and authenticity come together, giving an unforgettable experience to those lucky enough to discover this gem of the Greek Dodecanese.

Kastellorizo (Dodecanese)

Kastellorizo (Dodecanese)

The last Greek-speaking stronghold on the way to the East, Kastellorizo is remote (about 70 miles from Rhodes) and isolated. The traveler who decides to reach it will be rewarded by the magical atmosphere here.

The small harbor is a perfect postcard of the Mediterranean-with the low yellow houses, the cozy pink and green taverns offering the catch of the day, and the chimes of the bell tower reminding you that time has not stood still! The alleys invite you to discover the small village, and the walk to the old fort will repay the effort of the climb with an extraordinary view. The seabed at Kastellorizo is wonderful, giant groupers and starfish populate this turquoise sea where turtles swim undisturbed among the harbor boats and in secluded bays.

Symi (Dodecanese)

Symi (Dodecanese)

Symi is one of our favorite destinations. It is a unique island where the wild beauty of nature blends with beautiful and elegant architecture. Mountains covered with pine and fir trees falling to the sea, secluded beaches where goats come to the shore to drink the salt water, the famous monastery of Panormitis where pilgrims from all over the country ask for miracles-which are said to be often granted!

The nightlife in the main town is lively and fun, the most beautiful and elegant yachts moor in the harbor to dine in the renowned restaurants serving the famous Symi shrimp, a delicacy. Then you can move just away from the center, and the island will give you absolute silence, starry skies and the magical awakenings that only those who sail know!

Tilos (Dodecanese)

Tilos (Dodecanese)

Perhaps it is a secret I should not reveal - but Tilos has the most beautiful sea in Greece. The island is very large, but only Livadi (the harbor) is inhabited, and its idyllic white pebble beach and houses overlooking the sea will make you feel right at home.

For nature lovers, Tilos offers a number of hiking trails that lead to breathtaking landscapes, fascinating caves, and ancient monasteries. Tilos National Park is a paradise for birdwatchers, as it is home to a variety of migratory birds and endemic species.

Hydra (Saronic Islands)

Hydra (Saronic Islands)

Hydra, what's not to love? The tiny marble-paved harbor surrounding the beautiful Venetian bell tower, the quaint faces of the locals, the comings and goings of donkeys (the island's only means of transportation), the elegant cafes and authentic atmosphere, the beautiful museum, the contemporary art exhibits, the old houses restored with love and taste.

Here there are endless walks for those who want to get lost. In Hydra you can breathe worldliness and class, but with simplicity and silence. Note that the only way to reach Hydra's beautiful beaches is by water cab or sailboat!

Spetses (Saronic Gulf)

Spetses (Saronic Gulf)

Where the houses are painted white or delicate pastel colors, the roofs tiled, the gardens host the blooming bougainvillea - and many other beautiful Mediterranean plants. The streets, including the square overlooking the harbor, are paved with smooth black and white stones - where townspeople travel in horse-drawn carriages, while visitors stroll along the coastal road.

In Spetses, life flows slowly, everything is taken care of, the architecture elegant and the old cafes - it is the island of the great shipowners, so the old port exudes history and charm. Evenings in Spetses are magical - with candle-lit tables, old wooden boats leaning along the shoreline - making it a truly authentic and secluded island.

Guides & tips

Greece by sailboat

Greece by sailboat

Cyclades islands by sailboat

Cyclades islands by sailboat

 Ionian Islands by sailboat

 Ionian Islands by sailboat

 Sardinia on a sailing boat

 Sardinia on a sailing boat

Sailing vacations for singles and solo travellers

Sailing vacations for singles and solo travellers

Balearic Islands by sailboat

Balearic Islands by sailboat

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964