Cyclades Sailing Itinerary

Enjoy the Greek Paradise of the Cyclades

Cyclades Sailing Itinerary

Archaeological ruins, rugged landscapes, and the Aegean Sea make the Cyclades the ideal sailing destination, with plenty of islands and sights to explore.

We confidently recommend our Cyclades Sailing Itinerary, for those who want to experience light and stronger winds throughout the day.

We have carefully selected our Cyclades Sailing Itinerary, to provide an experienced to advanced level of sailing. The Cyclades Sailing Itinerary is ideal for families and couples who want to explore the beautiful Aegean sea, and experience a wilder and more dramatic area of Greece, the Cyclades Islands.

Our Guide to the Cyclades Sailing Itinerary

The Cyclades is a collection of over 220 islands located southeast of mainland Greece. The circular series of islands is located in the heart of the Aegean Sea. Many of the islands are famous for their blue and white architecture, food scenes, sophistication and sun-drenched rocks, as well as one of a kind archaeological sites.

The Cyclades’ large collection of islands make the perfect sailing destination for everyone. The number of islands in the collection means that there are a large number of sailing options available depending on what and where people want to visit. Two of the main sailing routes start from Athens and Paros.

The Cyclades Sailing Itinerary starts in Athens at Alimos Marina and continues to the islands of Kea, Syros, Mykonos, Naxos, Koufonissia Islets, and ends in Paros. Alternatively, a route from Paros is also available, depending on the desired islands.

From the blue and white architecture of Mykonos to the picturesque beaches and traditional villages in Paros, each destination is completely unique. This itinerary has something for everyone to admire and enjoy.

  • Getting There

    Athens can be easily accessed from all over Europe, as well as through many International Airports, as it’s Greece’s capital city and has the biggest airport (ATH- Eleftherios Venizelos) in the country with a large number of flights daily, year round. Alimos Marina can be accessed from Athens airport via taxi and the journey is only 35 minutes long. From Paros, flights can be taken to mainland Greece and beyond.

  • Mooring

    Mooring in most of the places in our Cyclades Sailing Itinerary is “stern to” with mooring lines or anchor at the bow. You can also enjoy “free-swinging” in idyllic, secluded bays, with or without long-lines ashore. If you want to visit a couple of private marinas, you should expect a relatively high fee per night.

  • Weather

    The weather in the Cyclades is warm in summer with varying winds, which can become strong when the Meltemi hits. This makes it the perfect sailing destination for intermediate or advanced sailors.

Cyclades Sailing Itinerary – From/to: Athens

Discover the History, Beautiful Beaches and Gorgeous Blue Waters of the Cyclades

Day 1

Athens, Alimos Marina

Our Cyclades Sailing Itinerary begins in Athens, at Alimos Marina. Alimos Marina is one of the largest marinas in Greece and is the perfect place to arrive at your sailing boat and rest before beginning your Cyclades Sailing Itinerary. The marina is located close to a large number of bars, restaurants and a supermarket to stock up on necessities for your trip.

Overnight Anchorage: The Alimos Marina has over 100 berths for boats to anchor.

Book in Advance: Telephone Center +30.210.9880000 or email on

Day 2

Athens, Alimos Marina → Kythnos, Merichas (40NM)

Day two of our Cyclades Sailing Itinerary we depart from Athens and head to the island of Kythnos. Kythnos is an island filled with colorful flowers, bright blue waters, golden beaches and on your way to the port of Merichas you can stop and explore one of Greece’s largest caves – Katafiki Cave in Dryopida. You can also stop around the island to swim in the picturesque bays.

Overnight Anchorage: Merichas is the main port on the west coast of the island. The port has a ferry dock, and a small pier. While there is no serrate place to moor inside the port, just outside of the seawall there are arrows which indicate positions where mooring is available.

Day 3

Kythnos Mericha → Syros (20NM)

On day three of our itinerary, we head from Kythnos to the island of Syros. Syros is a small island filled with spectacular coloured buildings and culture, and is predominately off the regular tourist track. A great place to spend the night is in Finikas, on the southwest coast of the island. This is a quiet village filled with taverns, bars, and coffee shops, and is a great place to anchor as it offers good protection from the Meltemi.

Overnight Anchorage: Mooring is available at a small marina (spaces limited) as well as anchoring offshore outside the breakwater. 

Book In Advance: Iroon Polytechniou, 84100 Syros, Greece, Tel:+30 22810 85803 & 86070 Fax:+30 22810 85803,VHF Channel 12

Day 4

Syros → Mykonos (18NM)
Day four brings our Cyclades Sailing Itinerary to the famous island of Mykonos. The island is known for its perfect white architecture and nightlife scene. Here you can anchor at Mykonos Old Port harbour, in the centre of everything or choose to anchor in the beautiful beaches at Aghia Anna bay.

Overnight Anchorage
: Mykonos Old Port in the harbor or at Aghia Anna bay off-shore with a predominantly sandy floor.

Day 5

Mykonos → Kea (44NM)

Just 44 NM away from Mykonos is the large bay of Agios Nikolaos on the northeast side of Kea. Agios Nikolaos is one of the safest naturally formed harbours in the Aegean Sea area. Kea is a beautiful island filled with ancient ruins, quaint towns, and cosmopolitan and friendly locals. Old churches, beaches, mills, towers, and windmills fill the island with picture-perfect locations and exciting places to discover. We suggest anchoring in Agios Nikolaos for your first night (a marina to the northeast of the bay is Vourkari).

Overnight Anchorage: In Vourkari either off-shore anchorage or stern-to at the quay.

Book in Advance: Port Authority +30 22850 22300

Day 6

Kea → Sounion (12NM)

Sounion is located on the southern most point of mainland Greece. It was once fortified to protect the city of Athens. Sounion is home to the unique Temple of Poseidon (Greek Goddess of the Sea), on the top of the cliffs you can find this picturesque building, which also offers a great place to watch the sunset from. Sounion is known for it’s historic buildings, spirit and achievements, while also being a great place to swim and relax.

Overnight Anchorage: Sounion Bay or Legrana Bay are great places to drop your anchor and spend the night.

Day 7

Sounion → Athens Alimos (25NM)

Our Cyclades Sailing Itinerary ends back in Athens, at Alimos Marina. Alimos Marina is one of the largest marinas in Greece and is the perfect place to depart from your sailing boat and rest before beginning your journey onwards or home. The marina is located close to a large number of bars, restaurants and a supermarket to stock up on necessities before your departure.

Overnight Anchorage: The Alimos Marina has over 100 berths for boats to anchor.

Book in Advance: Telephone Center +30.210.9880000 or email on

Cyclades Sailing Itinerary Departing and Returning From Paros

Day 1

Paros Paroikia

Paroikia is the main port on the northwest coast of Paros. Paroikia has a large number of taverns, bars and shops to look around. There are also white sandy beaches to explore along with ancient monuments and attractive Greek villages.

Overnight Anchorage: The port of Paroikia has a large number of mooring lines available, but if these are occupied there are a large number of small inlets and shelter can be found and anchors can be dropped.

Book in Advance
: +306942772023

Day 2

Paros, Paroikia → Kamares, Sifnos (30NM)

Kamares, Sifnos is a family friendly beach town with a large beachfront area. On the journey you will pass by the surrounding islands of Paros which are the ideal places to anchor for lunch or for a swim. The island of Sifnos is home to cobble stone streets and striking cliff tops. The island only has one port – Kamares.

Overnight Anchorage: Kamares is the only port on the island and provides great shelter from the strong winds.

Day 3

Kamares, Sifnos → Folegandros

Day 3 sees the Cyclades Sailing Itinerary stop at the picturesque adventurous island of Folegandros, a great place for adventure lovers with mountainous hiking along with beautiful beaches. This predominately untouched island is filled with authentic Greek character.

Overnight Anchoring: Karavostasi is the only harbor on the island and it is advised to moor stern-to inside the quay to avoid the wind.

Day 4

Folegandros → Santorini (30NM)

Santorini is one of the most famous and iconic islands in Greece with its perfect white washed buildings with dark blue roofs. Santorini is a mountainous island complete with an active volcano, white sandy beaches and a thriving nightlife; this island has something for everyone to enjoy. Santorini is a sailing heaven with lots of inlets to explore and cliff faces to marvel at.

Overnight Anchoring: Skala is a port located deep in the caldera. It is a great place to moor overnight to avoid the powerful winds, it is advised to moor with a long line to a mooring buoy from the bow and tie the stern to the quay or bay platforms.

Day 5

Santorini → Amorgos (30NM)

Amorgos is an island full of serenity and antiquity along with intense spiritual vibes. Many consider this island the most beautiful in the Aegean Sea.

Overnight Anchoring: The bay of Aegiali is a great place to drop anchor for the night, the northwest of the bay has a mud seabed.

Book in Advance: Port Authority +30 22850 22300

Day 6

Amorgos → Paros Naoussa Bay (54NM)

Paros is filled with natural beauty and a perfect turquoise sea. This stylish and fashionable resort is a great place to explore and finish off your trip. Naoussa is a great place to drop anchor, there is town and lots of places to explore.

Overnight Anchorage: Naoussa has a marina with plenty of anchorage available.

Book in Advance
: +306942772023

Day 7

Paros Naoussa Bay → Paros Paroikia (12NM)

On day 7 our itinerary departs from Paros Naoussa Bay back to our starting point of Paros Paroikia. On the way you can stop and swim in a small inlet or have lunch anchored in a bay with spectacular views out to sea.

Overnight Anchorage: The port of Paroikia has a large number of mooring lines available, but if these are occupied there are a large number of small inlets where shelter can be found.

Indicative Yachts and Prices For the Cyclades Sailing Itinerary

cyclades sailing itinerary

Jeanneau Sun Odyssey 439 – Prices From 2,000 £

cyclades sailing itinerary

Lucia 40 – Prices from 3,000£

cyclades sailing itinerary

Lagoon 420 – Prices from 2,700£

cyclades sailing itinerary

Benetteau Oceanis 40 – Prices From 1,500£


*All prices are per boat, for one week. For more yacht options and exact prices, please contact us

Amazing Sailing Experiences

Our Amazing Customers

  • Great family vacation.

    I didn't think sailing with my family would be so much fun...

    Sailing for the first time.

    Alex USA

  • I recommendate them !

    Everything went smooth, the paper processing, special requests and the specs of tht check-in procedure. Boat was also in good shape, so no complaints and a worry free holiday...

    We had a great experience with booking through sailchecker.

    <read more>

    Dick USA

  • Great service from Kate.

    Informative and looked for the best value for our family. Very good customer service on this side and in Greece. Great boat and skipper...

    Fantastic holiday from start to finish.

    <read more>

    Angela United Kingdom

  • Very professional outfit!

    They were very responsive and very quick to answer questions via email and instant chat. They had extensive knowledge of the area...

    We will most definitely use their services for our next bareboat sailing vacation.

    <read more>

    Kirsten W.
    Kirsten W. USA

  • Sail checker were professional from start to finish - we wouldn’t book through anyone else!

    Sailchecker were professional from start to finish - and were awesome dealing with a problem! Our first Yacht had serious issues and sail checker helped us to resolve it...

    They are easy to deal with, straightforward and honest and I would recommend them to anyone planning a charter holiday.

    <read more>

    Kat, H.
    Kat, H. UK

  • Coronavirus pandemic support has been brilliant!

    During the Coronavirus pandemic, Kate and her colleagues at Sailchecker have performed brilliantly. They have been considerate and highly efficient in re-organising our Turkey charter and also provided lots of assistance in getting our Yacht Security Deposit insurance policy transferred to match our revised charter dates.

    Truly worthy of a 5 star rating!

    <read more>

    Alan, R.
    Alan, R. UK

  • Sailing is the perfect family holiday.

    Would I go sailing again? OMG yes! Sailing is the perfect family holiday. Boys loved the activities, I enjoy relaxing as well... arranged a sailing cruise her family of 2 sons, daughter & hubby in the BVI with their own.

    Anne USA

  •  Thank you sooo much! It was sail in the day… party at night. We couldn't have wanted a better skipper or a Spring Break!  Good times...

    Arranged for 6 friends to sail Spring Break in the British Virgin Islands for under $500 each.

    Tim USA

  • We had an absolute blast !!

    All bookings and confirmations was always accurate with no delays. Our boat was also fabulously maintained and the Skipper new the area extremely well...

    Everything was down to the tee.

    <read more>

    Pieter Van R.
    Pieter Van R. Netherlands
SailChecker Yacht Charter and Sailing Worldwide Logo TrustPilot 4.9/5 Stars

Rated 4.9 out of 5 based on 215 reviews on Trustpilot

Got a Burning Question About Cyclades Sailing Itinerary?

We’re Happy to Answer Any Yacht Charter & Sailing Question

Leave us a quick question here, or call your local office, the numbers are located in the footer below. When not arrange a call back?

girl at desk at yacht charter show

Leave a Comment

Start typing and press Enter to search

The Fastest Way to Our Award Winning Charter Service Starts Here >>>
Get Started