The Cyclades Overview
The Cyclades comprise 200 islands south of Athens - explore them with a Greek sailing island adventure from Off The Beaten Tack

The Cyclades

The Cyclades comprise of about 220 islands south of Athens, the most well known being Mykonos and Santoríni which is where our tours will start and finish. We visit popular islands such as Ios, Paros, Milos, Naxos and Amorgos.

Other islands include Andros, Antíparos, Delos, Ios, Kea, kilimons, Kithnos, Folegandros, Serifos, Sífnos, Síkinos, Syros and Tinos. That leaves 100’s of islands for us to explore alone!

Skipper Jimmy’s favourite islands are the Lesser Cyclades, a group of tiny, unspoilt islands, some of which remain uninhabited and hide the relics of an ancient past.

All of the islands are surrounded by crystal clear turquoise waters with a mixture of rugged coastline with impressive cliffs and gorgeous sandy beaches offering safe anchorages and opportunity to explore on land as well as at sea. The architecture is very traditional with whitewashed buildings in contrast to the bright blue shutters. There are hidden gems everywhere you visit.

The islands are peaks of a submerged mountainous terrain, with the exception of two volcanic islands, Milos and Santorini. The climate is generally dry and mild and local agricultural produce includes wine, fruit, wheat, olive oil, and tobacco.

The main islands offer interesting culture and history, good places to eat and a vibrant night life with shops open late and charming tavernas.

There are plenty of uninhabited islands to explore and enjoy complete isolation, BBQ’s on the beach and the option to sleep under the stars onshore.


The best ways to join the yacht is to either fly direct to Santorini or Mykonos, or fly to Athens then use the excellent ferry service from Pireaus (Athens) to the islands. We recommend you set aside a couple of extra days at either end of the trip to spend more time in Santorini and Mykonos which are destinations in their own right.

If you had a bird's eye view the Greek Cyclades, they would look like an intriguing mosaic of 20 tufts of verdant earth floating on the turquoise waters of the Aegean sea. It's an incredible formation created by the geological changes that took place millions of years ago.

According to the Greek mythology, Poseidon, God of the sea, was so furious at the behaviour of the Cyclades nymphs that he turned them into islands.

However they were formed, The Cyclades — which means the Sacred islands around Delos — their beauty and dazzling light can lend itself to a spot of spirituality.

For most of the year the wild rugged volcanic scenery remains whitewashed with sugar cubed Cycladic architecture that looks superb against the dark or vegetal backdrop with the deep blue sea lapping at their shores. Here are six suggestions.




Some say the most beguiling and popular island of this Aegean archipelago is Santorini. Everyone will have seen that iconic image — you know, the one with the cliff-top blue-domed church standing out amid shimmering white architecture that looks dazzling against the blue skies and seas. 

The island of Santorini is famous for breathtaking views, beautiful sunsets and its very own active volcano. Putting natural beauty aside, Santorini is also teeming with cultural attractions and architectural splendours. 

There are beaches, a pebbly one at Kamari and a black sand ones at Perissa and Karterados and these are overlooked by jagged cliffs and a brilliant light that seems peculiar to the cyclades — it can be mesmerising.

The hillside towns of Fira and Oia are quaint with sometimes steep steps and knotted alleyways and make for idyllic afternoon exploration. And in the evenings the roof terraces of restaurants are light and alive with diners enjoying libations and alfresco dinner in the warm night air. This island is all about relaxing sophistication.



With its pristine sandy beaches, crystal blue waters and cosmopolitan nightlife, it's no wonder that holidays in Mykonos are among the most popular in Greece. Mykonos seamlessly blends its whitewashed cube-shaped houses with its picturesque fishing village environment, ensuring that all visitors on holiday in Mykonos are embraced by its tranquil surroundings. For such a small island - just 16 kms (10 miles) long - it offers a uniquely varied selection of clubs, bars and great shops, so you can be sure that holidays in Mykonos will never get boring.

Mykonos Town, with its picture perfect white washed houses and cobbled streets is quite simply one of the most attractive towns in the Greek islands. With an array of excellent bars and restaurants to rival anywhere in the Mediterranean and its opportunities for designer shopping in the narrow streets behind the harbour, Mykonos Town is the place to be seen as many a celebrity will testify.



This is the largest of the Greek Islands in the Aegean Sea and when you arrive by boat you will be met with its most famous archaelogical site — the Portara, the doorway to the ancient temple of Apollo built in 522 BC. The island is home to the highest mountain in the Cyclades — Mount Zeus — which is the source of much mythology. They say that this was the nuptial isle of the Dionysus, the God of wine. That's why there is a sanctuary dedicated to him. It's coastline is a doily of sensational beaches, some secluded. Mikri and Vila in the west are beloved by windsurfers. 

Inland its incredibly mountainous and villages seem to appear out of the fertile valleys and there are plenty of fields and olive groves. Its harbour is in the capital where several alleys lead steeply to the citadel, a landmark that can be seen for miles and elsewhere there are old churches, monasteries and Venetian castles and homes.





There are two completely contrasting areas to Ios. One offers peace and tranquillity with 365 churches and the other offering  great nightlife and beach parties that start early and last throughout the night. Near to Chora there is a kilometre stretch of beach peppered with bars and restaurants and myriad of water sports but there are more sedate options in the south of the island at Valmas beach or Kolitsani beach. The island also has the tranquil hillside village of Chora, probably the most picturesque in all the Cyclades. The views from its highest point are simply breathtaking. OTBT have a good relationship with a local spa which offers amazing quality food and a variety of treatments.



Paros, a ferry hub and a beautiful Venetian port, is considered as one of the most beautiful islands defined by its beaches and quaint villages. Parikia, the island’s main town and port is filled with narrow, winding streets which were originally intended to confuse any invaders, giving the locals time to escape! The town now boasts an atmospheric and intriguing mix of the old and new, with its white-washed buildings and an excellent selection of restaurants, bars and shops.

The most popular town is Naoussa. It was once an old fishing village but who would know? Today it is a popular cosmopolitan holiday destination. For a little culture visit the blue domed Byzantine Museum.



This world heritage site, located in the centre of the archipelago, is the birth place of Apollo and Artemis and in ancient times was the religious centre for the whole of Greece. The remarkable monuments, such as the Minoan Fountain and Temple of the Delians, and the impressive mosaics are certainly worthy of a visit.