Northern Cyclades Sailing Itinerary

Enjoy the Greek Paradise of the Cyclades

Northern 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 Northern Cyclades sailing itinerary for those who want to experience light and stronger winds throughout the day.

We have carefully selected our Northern Cyclades sailing itinerary to provide an experienced to advanced level of sailing. Our Northern 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 Northern 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 many sailing options are available depending on what and where people want to visit.

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

  • Getting There

    Athens can be easily accessed from all over Europe and 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 Northern Cyclades sailing itinerary is “stern to” with mooring lines or anchors 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.

Northern Cyclades Sailing Itinerary

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

Day 1

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

Our Northern 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 on your sailing boat. The marina is located close to many bars, restaurants and a supermarket to stock up on necessities for your trip.

The first stop on our itinerary is Kythnos, an island filled with colourful flowers, bright blue waters, and golden beaches. 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.

Day 2

Kythnos Mericha → Milos (40NM)

Day two of our Northern Cyclades sailing itinerary take us from Kythnos to Milos. Milos is one of the areas most laid back islands in the heart of the Aegean Sea.

Here you will find picturesque fishing villages to explore, a rich history and great dining options. A great place to visit is Sarakiniko beach. The beach is a great place to watch the sunset, with white rock formations and crystal waters. Don’t fret if you don’t like this beach; the island has over 40 other beaches.

Day 3

Milos → Paros (40NM)

From Milos, our route heads to Paros.

Paros is the perfect blend of traditional Greek with modern elements and Cycladic whitewashed buildings, a thriving nightlife, rural villages and beautiful beaches to drop anchor off and relax on.

The island has several marinas and overnight anchorages to moor at to visit the small ports, eat dinner at a restaurant and explore the local area.

Day 4

Paros → Naxos (10NM)

Day four of our Northern Cyclades sailing itinerary takes us to the largest of all islands in the Cyclades. Boasting impressive natural landscapes, mountains, rural villages and is one of the greenest islands in the Cyclades.

The island has many small coves to drop anchor and relax on your yacht or take a dip in the ocean. You can also drop anchor off one of the islands beautiful beaches – Mikri Vigla beach, Agios Georgios beach, or Plaka beach.

Day 5

Naxos → Mykonos (21NM)

Day five brings our Northern 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.

Day 6

Mykonos → Syros (18NM)

On day six of our itinerary, we head from Mykonos 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.

Day 7

Syros → Athens Alimos (40NM)

Our Northern 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.

The marina is close to many bars, restaurants, and supermarkets to stock up on necessities before your departure.

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 Our Northern Cyclades Sailing Itinerary?

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