The leading global boat rental platform
My wishlist
    Sign Up


    A romantic 7-day sailing itinerary in the Cyclades

    The picturesque, whitewashed buildings clinging to the hillsides of the Cyclades Islands provide one of the most well-known images of Greece. Narrow, winding streets, with pink-flowered bougainvillea trailing overhead and blue-painted shutters on tiny houses are everyone’s dream of a Greek island.    

    However, despite the undoubted charm of these islands, if you are sailing in the Cyclades in high summer it can be very breezy and requires careful planning. This sailing route is designed with this in mind, and due to the distances between islands, it may be better suited for more experienced sailors. You will visit up to six picture-postcard Greek islands, covering at least 125 nautical miles.

    What you can see and do on this route:Visit traditional island towns and villages with charming white-washed houses, rustic taverns, impressive ruins and beautiful beaches from the popular island of Mykonos. This route is for:This route is best for experienced sailors or skippered charters due to the strong winds in the Cyclades. Best time to go sailing:May-June and September-October Duration7 Days

    Day 1: Arrive in Mykonos

    view of the harbour in Mykonos
    Pelican in Mykonos' harbour

    If you charter a yacht from Mykonos you will pick up your boat from the new marina, which is 4 km north of the old town and airport. Yachts are not allowed into the bay or the old port. If you have a day to spare at the beginning or end of your holiday, you can still experience the attractions of Mykonos old town by taking a taxi there. Be sure to walk around the pretty harbour and explore the many alleyways, with their boutiques and gift shops. Don't forget to say hello to Petros the local Pelican! Tavernas and bars line the lively waterfront and the whole island gets very crowded in the summer months.

    Day 2: Mykonos to Naxos

    After you leave the marina at Mykonos, you will sail south and soon pass the sacred island of Delos, one of the most important archaeological sites in Greece. Providing you depart early enough on your yacht charter from Mykonos, you might choose to make a brief stop-over here at the restricted day anchorage, to enjoy a swim in the blue water - or to just breath in the history of the place for a little while.

    Delos, the mythological birthplace of Apollo, was at one time a major religious centre and port. On this historic island are the ruins of Doric temples, markets, an amphitheatre, mosaic floored houses and the iconic Terrace of Lions statues.

    ruins in Delos, Greece
    Take some time to explore the ruins of Delos, the first stop on your sailing holiday in the Cyclades.
    sun setting over the chapel and harbour in Naxos, Greece
    Sunset in Naxos

    Naxos town is approximately 23 nautical miles from Mykonos. From some distance away you will see the famous Portara arch, the gateway to the unfinished temple of Apollo. It is said that if you make a wish as you stand in the doorway you can feel the force of Apollo as he works to make your wish come true!

    Above the harbour the impressive Venetian castle dominates the town and is worth exploring. You will find all facilities in Naxos, including banks, supermarkets and many places to eat. The ‘Metaximas’ taverna, in the old market place, is popular with both locals and visitors – you may find yourself seated in the picturesque narrow lane or on the tiny terrace. The Naxos cheese and horta (wild greens) are recommended - as well as the local seafood, of course.

    Want to find a boat for this route?

    Make a request using the button below and we'll find you the perfect boat. 

    +44 20 3318 3641
    Mon-Sun: 9-9pm CET | Sat-Sun: 11-7pm CET

    Day 3: Naxos to Paros

    Paros is a relatively short hop from Naxos. You will sail 6 nautical miles to the north-west, going round the top of Paros. The island of Paros was historically known for its fine white marble - it was used for the sculpture of the Venus de Milo and also for the temples on Delos. Abandoned marble quarries or mines can be seen around the island.

    There are two main harbours that you can visit on Paros. On the west coast, well-sheltered from the Meltemi winds, is the main port of Parikia. You can moor stern-to on the yacht quay, separated from the bustle of the main ferry port. On the north coast is the smaller port of Naoussa, based on an old fishing village.

    fishing harbour, Naoussa, Paros
    Fishing harbour of Naoussa on Paros island
    waterfront restaurant in naousa, paros
    When dining onboard, enjoy an authentic meal at a traditional taverna in Paros.

    The yacht quay was completely rebuilt in 2011; there is now space for over 70 yachts. In fine weather, you can anchor in the bays to the west and north-west of the harbour, just a short dinghy trip away from town. Naoussa is undoubtedly one of the most beautiful harbour villages in Greece, a photographer’s dream, with whitewashed houses surrounding the waterfront and a maze of narrow lanes to explore. There are plenty of gift shops and boutiques here, as well as many tavernas.

    Naoussa is undoubtedly one of the most beautiful harbour villages in Greece...

    Day 4: Paros to Serifos

    On your yacht charter from Mykonos, your longest sail will be from Paros to the island of Serifos. A distance of 35 miles due west will bring you to the large bay and harbour of Livhadi. Mass tourism has not reached Serifos and it retains an authentic atmosphere. In the distance as you approach you will see the ancient chora town perched on the hilltop, its white sugar cube houses clinging to the slopes. The chora has commanding views over the Aegean Sea and is certainly worth exploring.

    You can catch a bus from near the harbour if you don't fancy the steep walk - although coming back down is much easier. You can follow the old donkey tracks, which are well signposted. You will be amazed by the picturesque narrow streets, the white buildings with coloured shutters, and the tiny churches. Don’t forget to take your camera! It is also possible to anchor in the bay to the south of the harbour, where you can take your dinghy ashore and walk along the lovely beach, tamarisk trees giving natural shade in the heat of the day.

    chora in serifos
    Visit the enchanting chora of Serifos

    Day 5: Serifos to Kithnos

    Lunch at Xereolithia taverna, Loutra, Kithnos.
    Lunch at a typical taverna in Loutra

    Sailing north for 21 nautical miles will bring you to the island of Kithnos. You have several alternatives here for mooring, according to the wind conditions. The pretty harbour of Loutra, on the north-west coast, is close to some thermal springs. Their healing properties have been sought from ancient times. The mineral waters can still be seen flowing near the port – the spring water contains traces of the iron that was once mined on the island. There is also an important archaeological site nearby, the oldest known habitation in the Cyclades. At Loutra, the ‘Cavo d’Oro’ is an authentic taverna on the water’s edge. You might find some friendly Greek cats sitting near your table!  ​

    Alternatively, you could sail to the west coast of Kithnos and anchor in the shelter of the fabulous Sand Bar Bay at Fikhiada, which is very well protected from both the Meltemi and southerly winds. This is an idyllic spot, with glorious beaches either side of the sandbar, leading you to the little islet beyond. There is a small taverna close to the beach, with wonderful sunset views over the bay. Merikhas, also on the west coast, is the main port of Kithnos, where large ferries arrive. There it is possible to moor on the quay; you will find many cafes and tavernas with tables right on the beach itself. There are ATMs, a pharmacy, bakery and supermarket - and you can readily hire a car or scooter. This is the main tourist destination on the island and tends to get busy in the summer months.

    Boats anchored in Sand Bar Bay

    Day 6: Kithnos to Syros

    Colorful street in Syros, Greece
    Stroll the streets of Syros while on your yacht charter holiday in the Cyclades

    From Merikhas, the island of Syros is 20 miles due east, slightly more if you sail round from Sand Bar bay. You will head for the little harbour at Finikas, on the south-west coast of Syros. You might find space on the outside of the harbour wall, or you can anchor close by.  The harbour is very well protected from the capricious Meltemi winds that blow in the summer months. Finikas is a pretty village, with a few places to eat and a good bakery. The ‘Dios Xeiros’, a family run taverna close to the harbour, serves traditional fennel pies and a delicious tomato, mint and feta salad. 

    Finikas is very well protected from the capricious Meltemi winds that blow in the summer months.

    If the weather is kind, you may well choose to sail round the south side of Syros to Ermoupolis, where you are likely to find many yachts moored on the extensive town quay. The busy waterfront is lined with cafes and bars. This vibrant and most interesting town is the capital of the Cyclades island group - it is the main commercial and business centre of the islands. There is a large hospital in Ermoupolis, as well as a university, law courts and a theatre. Many large ferries arrive here and the town is always bustling, even in the winter. However the large harbour, while providing good shelter from the prevailing Northerly winds, is prone to swell if these winds are strong - although safe it can get uncomfortable on the quay.

    The town of Ermoupolis, built on two hills
    View of Ermoupolis

    Day 7: Syros to Mykonos

    windmills of Mykonos
    Enjoy the views of the Mykonos' distinctive windmills.

    You will sail 25 miles NE from Finikhas back to Mykonos harbour (or less from Ermoupolis). You will see the island of Tinos in the distance on your port side. As you approach Mykonos you will pass the north coast of the island of Rineia, with its indented and rocky coastline. 

    After reaching the marina at Mykonos, you can relax and take a taxi into the old town to watch the sun setting behind the famous windmills on the hill behind the town. They were built by the Venetians in the 16th century to grind wheat. One of the windmills is now a museum.

    This sailing itinerary for yacht charter holidays in Mykonos was created by Georgina Moon, a passionate writer, blogger and sailor. To learn more about sailing in Greece, check out Georgina's guest post in our Magazine

    Boats for this Route