There are more than 220 islands in the Cyclades, with more than 30 being inhabited. Besides the main destinations of Mykonos and Santorini there are more than 20 other islands that are interesting to visit. The islands overall are characterized by their mountainous geology rising from the Aegean with many coves and sandy beaches all along its coasts. Many have been inhabited continuously for more than 2000 years and have the antiquities to prove it. The people are known to be some of the friendliest in Greece and this is enforced by their openness from several decades of tourism while still keeping their local traditions. Below you can find a short list of information for key Cycladic islands ideal for your sailing trip! However, beside these islands there are plenty more one can enjoy visiting like Folegandros, Tzia, Ios, Syros, Sikinos. If you need information on one or more of the islands not analyzed below please feel free to contact us and we will send you detailed information along with customized and suggested itineraries to enjoy the full Cycladic Sailing Experience!
Mykonos is one of Greece’s most popular destinations, and for good reason. This small Cycladic island with its characteristic architecture and windmills, its beautiful beaches, and its famous windmills, has been a favorite of the global jet set since the 60s and the flamboyant gay community since the 70s. The Windy Island as it’s known in Greece continues to be a favorite destination for all those looking for the quintessential Greek island experience. Set next to Delos, Mykonos is a popular destination for historical reasons as well! During the Golden Age of Athens, the island was considered to be holly, while Athens stored its gold reserve there. Make sure to walk through the Matogiannia street where you can find small shops with all known international luxury brands, visit Small Venice for a drink by the sea and hop on a taxi to Ano Mera to eat at the traditional tavern “Oti Apomeine” for a tasting of famous traditional, local cuisine!
Santorini is truly unique not only for Greece but for the entire world. This iconic destination is most known for its breathtaking views of the red and brown layers of volcanic ash that make up its famous cliffs. In fact everything seems to be perched on these cliffs from its many boutique luxury hotels to its fabulous restaurants. It’s no surprise that you will also find yourself spending most of your time on these cliffs taking in the views and not believing your eyes of the beauty and also it’s no surprise that it consistently shows up on the top 10 lists of the most romantic vacation spots in the world. Make sure to visit the volcano island opposite Kaldera where you can anchor and have a swim by the black and red stoned beaches. You can also take a donkey ride down to Ammoudi from Oia, swim, eat lunch and return back up to take in the Oia’s famous sunset! Santorini is also known for its vineyards so make sure to visit one of the many wineries and get a first-hand experience of how the volcanic soil produces some of the best wines in Greece.
The largest island of the Cyclades, Naxos has many hidden gems. With its endless sandy beaches, the cedar forests in the south, Venetian castle and towers, byzantine churches, and archaeological sites there is much to see and do here. Naxos also has several of the most well preserved Cycladic villages located inland and worth visiting both for their architecture but also their food and culture. The island itself has a large amount of agricultural production so make sure to taste some of their local cheeses and their citrus liqueur. Don’t miss the ancient temple of Apollo in Portara, a huge marble gate and the single remaining part of an unfinished temple of Apollo of 530 BC, is Naxos’s emblem and main landmark. Standing on the islet of Palatia, at the entrance to Naxos harbor, it comprises four marble parts weighing about 20 tons each.
Paros is one of the most visited islands in the Cyclades because of both its location and the experiences it offers. It’s as much a family destination with its shallow bays, a faith destination for the 5th century AD church of Ekatontapyliani, as it is an entertainment destination for the young to enjoy the island’s vibrant beach clubs and night clubs. It also is one of the major windsurfing destinations in Greece having for many years hosted a leg of the World championship. Make sure to walk through the streets in Paroikia behind the castle, eat dinner at one of the sailor’s ouzeris in the small old port in Naousa, and visit Lefkes for its beauty. Located just a 15 minute ferry ride across the sea is Antiparos, a smaller version of Paros great for those looking for the beaten track destinations.
Sifnos has been popular for many years for offering a higher quality experience in the Cyclades. The main reason for this is the high level of service the locals have been able to offer. Without allowing for tourism development to take over their island, most of their hotels and restaurants are owned by generations of locals who care about the reputation of their island and offer only the best to their guests. A great destination for both families on the one hand but also couples on the other. Don’t leave with buying some of their famous local ceramics, some of the best in Greece. Sifnos is also known as a wedding island as it has some of the most picturesque small churches ideal for marriages. While there you certainly need to visit the monastery of Panagia Chryssopigi which is literally on a rock in the sea but also the small church Kastro (Castle) which is hanging on a cliff and has a breathtaking view!
Milos is the second volcanic island in the Cyclades, after Santorini of course, and as such the island is characterized by its natural resources including bentonite, perlite and small quantities of kaolin. Milos was a also source of obsidian during the Neolithic ages. While made famous in the 19th century by the discovery of the classical masterpiece of “Venus de Milo” exhibited at the Louvre, the island now holds the reputation of having some of the best beaches in Greece to visit and explore. Visiting Milos with a yacht is ideal as you can explore some of its hidden coves and scenic rock formations such as Kleftiko (photo on the left) and also take a day trip to beautiful Kimolos famous for its production of chalk.
For many years Koufonissi has remained the secret of the Athenian bourgeois boheme. With difficult access from Athens, must connect through Naxos, and not much selection for accommodation, the island still remains an off the beaten track destinations. A place where a car is not needed as the islands are very small and easy to walk or cycle, Koufonissia is one of the favorite destinations for yachts. While many yachts anchor around the beautiful beaches and bays it is a place where the Cycladic weather must be taken under consideration before setting the course as the “meltemi” (Northern wind) grows strong during August making sailing a considerable challenge!
The Dodecanese, in the southeastern Aegean Sea, is a group of Greek islands known for their medieval castles, Byzantine churches, beaches and ancient archaeological sites. The group consists of 12 larger plus 150 smaller Greek Islands, 26 of which are inhabited. Apart from the most historically important and well-known islands like Rhodes and Kos, there are several smaller islands of exquisite beauty like Astipalea, Karpathos, Kasos, Leros, the volcanic Nisyros, Symi, Tilos and the picturesque Kastellorizo. Below you can find a short list of information for Rhodes, Kos and Kalimnos! However, if you need information on one or more of the islands not described below please feel free to contact us and we will send you detailed information along with customized and suggested itineraries to make the most out of your Dodecanese sailing experience!
Rhodes is the largest of the Dodecanese islands in terms of land area. The island is ideal for relaxation but also for those looking for an action-packed holiday! With its bright green hills, rich green valleys and uninterrupted line of golden beaches, Rhodes is truly a blessed place. Rhodes can either be your base for daily tours around the island or your starting point for a sailing trip to the rest of the Dodecanese islands. Make sure to visit Lindos, known as the “Pearl of Rhodes” on the southern tip of Rhodes where you can take a donkey ride to the top of the ancient citadel (Acropolis) and of course enjoy the popular nearby beaches. You can also visit Simi, a picturesque small island North of Rhodes where you can take a walk to the traditional town or enjoy a swim to one of its beautiful beaches and secluded bays.
Kos is a great family destination combining tons of history with crystal clear watered beaches. You will probably need three full days to see most of the antiquities as there are quite a lot. The most impressive of these is the Asclepeion which was a sacred hospital with several surrounding temples and buildings. But history is not all this island has to offer, so make sure to combine it with some of it’s beautiful beaches. In Kos you can enjoy the traditional Greek cuisine injected with lots of local elements and also try the local wine! The cosmopolitan boardwalk and the pier is ideal for a night walk in the town where you can enjoy your drinks by the sea! Make sure to visit the small volcanic island of Nisyros and have a guided walk through Stefanos, its largest volcano crater!
Famous for its sponges which are still collected to this day by its local divers, Kalymnos has remained a hidden treasure among the Greek islands. Forgotten in time, the islanders continue their traditional way of life without minding the visitors. Over the past few years, Kalymnos has become one of the world’s top climbing destinations and in late September there is a climbing festival with participants from all over the world. Sailing around Kalymnos is a unique experience as the island is full of secluded beaches and bays where the trees reach down the sea water and create a very beautiful scenery.