Embark on a Breathtaking Journey Through the Cyclades, Where the Beauty of Sailing Transcends Imagination

Feel the gentle embrace of the Aegean Sea as you navigate through a celestial archipelago adorned with dazzling, white-washed villages and vibrant azure domes. Sail past majestic cliffs that plunge into crystal-clear waters, inviting you to dive into an aquatic paradise.

Surrender to the serenity of secluded coves, where golden sunsets paint the sky and create an ethereal ambience. Immerse yourself in the rich tapestry of Greek culture, from savouring delectable Mediterranean cuisine to exploring ancient ruins perched atop island cliffs.

The Cyclades is a sailor’s dream, an enchanting symphony of nature and civilisation that beckons you to indulge in the captivating beauty surrounding you at every turn.

Cyclades yacht charter

This is a sample 7-day itinerary sailing in the Cyclades Islands, based on a bareboat or skippered yacht charter starting from Lavrion, Greece. Lavrion is a superb place to start and finish a yacht charter – it is easily accessible from Athens International Airport. It is the perfect launchpad for trips into the beautiful, rugged Cyclades.

This area has more reliable wind than the light Ionian and fickle Saronic, ideal for more experienced sailors. A great range of bareboat, skippered, and crewed yachts are available in the Cyclades.

Day 1


Just one hour away from Athens airport and a few hours’ sail from the first of the Cyclades Islands, the small town of Lavrion is a perfect starting location. Good facilities in the marina and a nearby supermarket make preparing for your charter a breeze, and there are plenty of good restaurants to soak up the Greek atmosphere on your first night.

A few miles south of the town, perched on the craggy headland of Cape Sounio, the Temple of Poseidon overlooks the Aegean Sea.

This 5th Century Doric structure dedicated to the ancient Greek god of the sea is well worth a visit if you have time on your first or last day, or there is even a sheltered bay just below the temple for a potential for a lunch or overnight stop.

Things to see and do

  • Visit the temple of Poseidon – only 15/20 minutes by taxi.
  • Provision your yacht ready for the week’s holiday.

Day 2

Lavrion to Kythnos (Kolona Bay)

On the Northwest coast of the island of Kythnos, Kolono Bay provides a picturesque anchorage sheltered from most wind directions.
The only hint of civilisation is a small tavern offering traditional Greek food overlooking the beautiful bay. If you’re feeling up to it, climb the hill to watch the sunset over the Aegean.

Things to see and do

  • Swimming in the bay’s crystal-clear sheltered waters is also an ideal opportunity for some water sports.
  • Climb up the hill to watch the breathtaking sunset.

Day 3

Kythnos to Paros (Naousa)

Set off early morning from Kolona Bay, as it’s a long sail down to Paros. But well worth getting the long sail done early in the week.
Naousa is a beautiful and lively town in a sheltered natural harbour on the northeast coast of Paros Island. A small marina with 1520 births offers a suitable mooring for the night.

There are also plenty of anchorages in the numerous bays. Admire the quintessential whitewashed sugar cube buildings and wander through the maze of streets before dining in a traditional taverna.

Things to see and do

  • Dine in one of the many Greek-style restaurants for authentic island cuisine.
  • Hire a car to explore more of the beautiful island.
  • Watch the sunset over the hills.

Day 4

Paros to Mykonos

A short hop northward takes you to the glamorous island of Mykonos. With its sandy beaches, startlingly white buildings, and vibrant nightlife, it is easy to see why people fall in love with this captivating island.

There is a medium-sized harbour north of the town, with water and some electric moorings, but generally, the facilities are basic. There is a supermarket close by. A long walk, bus or a quick taxi will get you into the main town.

Things to see and do

  • Hire scooters/cars to explore the breathtaking mountainous roads for a better island view. Including the legendary Mykonos Windmills.
  • Have a drink in one of the many serene cocktail bars.
  • Visit Matoyianni Street, famous for its shops. An ideal place to find a piece of Greece home with you.

Day 5

Mykonos to Siros

A comfortable sail west takes you to Ermoupoli on the Siros island, the Cyclades islands’ capital. As a busy shipping port and a large town, the quay has a lively atmosphere, where it is possible to moor stern-to with electric and water hookups and step straight off into the street.

There is a small marina to the south of the bay, mooring buoys, and places to anchor if you want a quieter evening.

Things to see and do

  • Hire a car to drive across the island for a sublime dinner in the fish restaurant in Kini Bay. Incredible views from the top of the hill overlooking Ermopouli and the sun setting across the water in Kini Bay.
  • Visit the Apollon Theatre – an architectural jewel in Emopouli.

Day 6
Siros to Kea

Leave in good time for a fairly long sail up to the island of Kea. On the northwest coast, Vourkari and Korissia are quaint and sheltered spots to moor for the night. There are some laid moorings in the bays and a few spots on the quay of each town.

Some fantastic restaurants, mountainous surroundings, and ancient buildings make Kea an elegant last night’s stay on the islands.

Things to see and do

  • Visit the Ancient Greek ruins in Korissia, overlooking the bay’s turquoise waters.
  • Go scuba diving with the Keadivers club – unparalleled visibility and great underwater landscapes – there is also the Patris Wreck nearby. Ask your HELM broker for contact assistance.