Island hopping in Greece on a sailboat – like a pro: a letter from two experts


written by Saxon • February 10, 2019

Who better to ask about island hopping in Greece than the experts? Renato and Lulu have been sailing the Greek Isles for well over a decade and have, very fortunately for all of us, decided to share their favourite islands. After taking some time to think back on their experiences, they have (somehow) managed to produce a list of just their top 10 islands in Greece. May this wisdom inspire your next sailing adventure!

Renato, a rally champion, has been sailing for work and pleasure for over 30 years. Together with Lulu, the couple have been exploring the world together for almost 14 years now. Having spent 6 years sailing the Ionian Sea, and 5 years sailing the Aegean – they set themselves the ambition of seeing the over 2,000 Greek Islands – and report that they haven’t too many left! Together they have also explored some of Greece by car, and gone further afield travelling in America, Asia, North America, and Africa side-by-side.

Among their list, Lulu and Renato were kind enough to include a number of their secret travel destinations in Greece – many of which are lesser-known, and rarely found in other guides and lists. So, perhaps you can join us in thanking them for sharing this rich insight on the Greek Isles!

If you are interested in learning more about their story, how they found each other, and what makes them tick – you can read our previous article about them, on A Lens Over The Sea.

Heard enough here? Ready to join them on their next sailing adventure? You can see their latest sailing experience listings on their Sailsquare profile.

  From Lulu:

10 Beautiful (lesser known) Greek Islands for your Bucket List

Hydra, what’s not to love? The tiny port paved with marble, surrounding the beautiful Venetian bell tower, the characterful faces of the locals, the comings and goings of donkeys (the only means of transport on the island), the elegant cafes and authentic atmosphere, the beautiful museum, the exhibitions of contemporary art, the ancient houses restored with love and taste.

Here you can take seemingly never ending walks for those who are looking to lose themselves. In Hydra, breath worldliness and class, but with simplicity and silence. Note that the only way you can get to the beautiful beaches of Hydra is either by water taxi, or by sailboat!

Where the houses painted white or delicate pastel colors, tiled roofs, gardens home to the bougainvillea blooms – and many of the other beautiful Mediterranean plants. The streets, including the square overlooking the port, are paved with polished white and black stones – where the town-folk travel by horse-drawn carriages, as visitors stroll along the coast line.

In Spetses life goes by slowly, everything is taken care of, elegant architecture and old cafes – it is the island of the great shipowners, therefore the ancient port exudes history and charm. The evenings in Spetses are magical – with the tables lit up by candles, the ancient boats of wood resting along the coastline – making it a truly authentic and secluded island.

Sifnos is one of the many Cycladic islands we love. The white cube-shaped houses topped with blue domes, the intense red of the bougainvillea hugging the towns, and a gentle breeze courtesy of the Meltemi.

In Sifnos you can learn the art of ceramics in one of the many laboratories scattered on the pier of Livadia (the main port), you can ascend the long set of stairs to reach the island’s monastery and its breathtaking view, you can go shopping in one of Apollonia’s beautiful craft jewelry boutiques, or you can discover one of the smaller villages of the island – like Vathi, that looks like it’s from a postcard, and where it is unforgettable to arrive by boat!

There are very few islands in Greece (and in the whole of the Mediterranean), that can compete with it on all fronts. Koufonissi is as beautiful and pure as the Aegean. Its sea is a constant blue presence that plays with skill and joy, drawing soft beaches of fine sand, tickling the white houses of the marina, creating shimmering blue coves, lagoons that look like pools, caves of porous rock that kiss the transparent water like we’ve never seen before.

The perfect Greek island?

It could really be Kato Koufonissi. Kato Koufonissi is suspended on a delicate, almost invisible thread seemingly ready to be broken. The port is the only village of the island, and it is small. In typical Cycladic style, you can expect: lime huts, and flowered blue balconies. But that’s not all. Koufonissi has something special because its simplicity is almost abstract from time and place. Take a beach, some fishing boats, add a few houses in the background and the sea – a colour of a deeper turquoise you can barely imagine. Here is a picture of the perfect fishing village. Here is Koufonissi.

A spectacular volcano, blond hills, small villages full of atmosphere, and a wonderful monastery overlooking the sea et voilà – Nisyros!

The island that you do not expect and is hard to leave for the infinite friendliness of the people, the exquisite cuisine. Pro tip: the tavern Aphroditi will serve you an exquisite Skordalia and a succulent octopus! Then finally you have the Caribbean lagoon of Giali, where you will have the most beautiful swim of your holidays.

In front of the beautiful island of Rhodes, there is a small paradise of beauty and perfection. The houses are painted in delicate pastel colors, balconies that look directly onto a crystalline sea, and a stunning church. Iit could be Portofino – but we are talking Greece, and far fewer tourists – the quay where the dock is home to only ten sailboat!

Here you can enjoy a fresh lobster in one of the fishing taverns of the tiny village of Chalki! Here where beauty can truly stop you in your tracks.

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

The small port is a perfect postcard of the Mediterranean – with low-sitting yellow houses, welcoming pink and green taverns offering the catch of the day, and the tolling of the bell tower to remind you that time hasn’t 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 seabeds of Kastellorizo ​​are wonderful, gigantic groupers and starfish populate this turquoise sea where turtles swim undisturbed among the harbor boats and in the secluded bays.

Scanning the Cyclades on a map, the last one you come across from Piraeus is perhaps the charm with which you have to confront yourself at least once in your life. Amorgos rises dramatically from the seabed of the Aegean and stretches like a solitary dragon for over 30km – blending the best of the culture, architecture, landscapes and beaches of an entire archipelago.

Amorgos is a noble, and manages to preserve its timeless atmosphere even in high season. it is not a wild party island, but rather a place for meditation and admiration, where you can walk among well-marked paths and swim in beaches that borrow colors from the sky and clouds. The Meltemi wind, can in winter lash out without mercy, but in summer always allows a sheltered coast to enjoy its wonderful sea. Despite have such a small population, Amorgos is in fact the true heart of Cycladic culture – the refinement of the beautiful Chora, some incredibly wild and isolated bays, and the incredible Chozoviotissa monastery. You will not want to leave!

Symi is one of our favorite destinations. It is a unique island, where the wild beauty of nature blends with the beautiful and elegant architecture. Mountains covered with pines and firs fall to the sea, isolated beaches where goats go to the shore to drink the salt water, the famous Panormitis monastery where pilgrims from all over the country ask for miracles – that are said to be often granted!

The nightlife of the main city is vibrant and fun, the most beautiful and elegant yachts moor in the harbor to dine in the renowned restaurants serving the famous Symi shrimp, a delight. 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 will know about!

Maybe it’s a secret that I should not reveal – but in Tilos there is the most beautiful sea in Greece. The island is very extensive, but only Livadi (the port) is inhabited and its idyllic white pebble beach and houses overlooking the sea will make consider moving here permanently. Paradise for those who love the sea, but also for those who want to take long walks.

Tilos is an ornithological oasis famous, for its delicious honey and an aromatic herb that grows only here, that together give a wonderful flavor to the roasted fish! A must visit is the ancient village, 7km from the port. Here you can have a beautiful dinner under the stars of the terrace with a breathtaking view of the tavern Kastro serving delicious dishes based on local, organic ingredients!