Sailing in
The Cyclades

a sailing trip is the best way to approach the wilderness of this beautiful archipelago, where the legends and the myths flow in the summer wind "the Meltemi".

A real sailing trip in the Cyclades

Sailing is our passion and we use the sails as much as possible, the Cyclades usually very windy conditions help us in that matter. A mix of real sailing,  exploring wild anchorages and climbing to white and blue villages, “chora”, which dominate each and every inhabited island.

The strategy

In the heart of the Cyclades, the island of Paros is the ideal place to begin your sailing holiday! The main advantage being that most neighbouring islands are within a single tack’s reach, meaning that we almost never have to zigzag against the wind.

The cruise offers the ideal distance from island to island ; long enough to have the feel of a real open-sea-sailing adventure, but short enough to limit sailing time from 2 to 4 hours.

Paros is a 4-hour ferry ride from Athens, 2 hours from Santorini and 1 hour from Mykonos.

The Meltemi from June to September

The local summer wind blowing from June to September is the fuel of the Archipelago! It cools the air temperature, clears up the sky and gives the Cyclades its authentic vibe which just doesn’t feel right without wind.

The Meltemi blows from a steady northerly direction throughout the archipelago, building up waves and confused seas, in unprotected areas for lack of islands fencing against waves to windward. In addition to wavy seas, in some areas the wind is accelerated while funnelling between islands, for instance. The wind can also be accelerated by an island itself (katabatic). Extended local knowledge and a careful planning of the itinerary are keys to a successful sailing cruise in the Cyclades. Depending on the strength of the Meltemi, your skipper will help you choose the best itinerary in order to ensure the smoothest possible and most exciting ride, while sailing from an island to the other. One of the most important factors to take into account, when planning the islands you wish to visit, is the wind and wave angle during the crossing. A yacht sailing or motoring against the wind would slam against the waves, get you wet and upset, while travelling at snail pace. To put it in a nut shell, sailing against the wind is what you absolutely do NOT want to experience!

The maps below show 2 different itinerary suggestions in stronger and lighter Meltemi conditions.

The East route

The East route – Ios, Amorgos and the small Cyclades – is definitely one of the favorite because it offers smoother sailing conditions with shorter hops between islands. As you can see on the map, almost the whole sailing area is sheltered by Despotiko, Paros, Antiparos and Naxos, which block the larger waves created by the prevailing north winds (Meltemi).

From, to

Miles

Hours

Paros - Ios

26

4-5

Ios - Schinoussa

21

3-4

Schin - Amorgos

20

3-4

Amorgos - bay

14

2-3

bay - Despotiko

31

4-5

Despotiko - Paros

15

3-4

The West route

The West route involves longer stretches between islands, in choppier seas, due to lack of shelter to windward. We recommend this route when the Meltemi is not too strong.

From, to

Miles

Hours

Paros - Sifnos

26

4-5

Sifnos - bay

14

2-3

bay - Folegandros

22

3-4

Folegandros - Ios

22

3-4

Ios - Schinoussa

21

3-4

Schinoussa - Paros

28

4-5

What’s the weather like in the “off season”?

In April, May and also from mid-September on, the winds are usually more variable. Low pressure systems appear more south in the Atlantic Ocean and they occasionally find their way into Greece after crossing the Mediterranean Sea.
Those low pressure systems usually bring south winds and little rain, but they do not last for long.

What people say...

Windfinders Sailing Cruises Cyclades
5.0
Based on 9 reviews
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Theresia Be
Theresia Be
15:18 29 Oct 20
I couldn't have imagined anything better for this October than sailing through the Cyclades with Istvan, his Cinderella and a friend. On this trip we got everything we could have wished for. Sunrises in lonely bays, dolphins, barbecues on the beach, hot springs, short hikes to small towns and much... more. Istvan is a lovely and helpful host with extraordinary knowledge about the area and about sailing. He is fun, spontaneous and flexible and stays focused when needed. It felt like traveling with a friend.read more
Laur-Andrei Tsk
Laur-Andrei Tsk
15:48 13 Oct 20
Best experience ever! Istvan is the best skipper ever and he treats like you are part of his family!
Ole Connor
Ole Connor
14:26 07 Sep 20
Fantastic Charter for Sailing into Cyclades with Skipper
frederique sauvez
frederique sauvez
07:37 01 Sep 20
Merveilleuses vacances à bord de Cinderella... Toutes les conditions réunies pour une croisière inoubliable.. Les Cyclades, un magnifique terrain d'aventure à la voile et merci surtout, Istvan pour ta gentillesse et ta bonne humeur... La famille au grand complet te donne rendez-vous l'annéee... prochaine.Frédériqueread more
Ole Connor
Ole Connor
07:12 26 Aug 20
Fantastic sailing trip from Paros to the cyclades. The boat to rent is a nice Dufour sailing boat and István the skipper knows all hidden beautiful places. We rented the sailing boat for one week from Paros to Antiparos, Sifnos, Poliagos, Folegandros, Ios, Schinoussa, Naxos, and some more Islands... from the small cyclades. The boat comes with four double bed rooms beside the skipper cabin with each one bathroom and could handle up to 8 charter guests.The skipper is very experienced into the area, which he knows for more than 19 year’s.We used the dingi boat for all land trips, snorkeling and cave visits. Sailing with Windfinders was a pleasure for us and it was the best way for me and my family to explore the islands of the cyclades by sailing.All sailing boat details we found on windfinders.netSee you next year again - Skipper:)read more
Annette Connor
Annette Connor
07:05 26 Aug 20
Great boat, great spots, unforgettable moments in one of the nicest areas in Greece. If you love sailing you are right here!
Next Reviews

Our family of 6 spent a week on board the Cinderella from 1-8 August as part of a longer multi island trip in the Cyclades. The week exploring the small Cyclades, hidden coves and quiet beaches, as well as decent sailing hours, with skipper Istvan turned out to be the highlight of our summer vacation. As we were advised by someone, the skipper and his/her knowledge of the area and the ability to get along with the guests can make or break the trip. With Istvan we hit bingo as he turned out a fantastic host for us and the kids, always willing to embark on an activity, on sea or on land. He knows his ship and the Aegean sea and that gives a very comfortable and safe feeling. Equally important, Istvan is really a nice guy, very relaxed about almost everything. Many thanks Istvan for a great week on board the Cinderella. 5/5 stars for sure.

Hoes family from Netherlands

We went on our first sailing trip ever five years ago and decided to choose Istvan Ferrare as a skipper. It was said that he is one of the most trustful skippers in the agean sea. After one week of sailing with him we got very good friends, got the sense of sailing and we NEVER felt unsafe!! Istvan has a great sense of humour and he is really sensitiv,he is an entertainer and skipper in one person . He would never risk something without thinking or do something unsafe. Istvan is an expert in finding the best places for you in the Agean. We really enjoyed every sailing week with him.

– Spreizer family from Austria

Just had the most amazing sailing holiday with Istvan and his boat Cinderella. We felt completely safe and secure on the boat, Istvan’s knowledge and experience is incredible and he took us to fabulous beauty spots that are not on the commercial path. We would recommend Windfinders to everyone with confidence…..Istvan is not intrusive and gives you space and privacy so if you are thinking of booking a sailing holiday then book Windfinders. Thanks Istvan

Susan from UK

Just back from a week of sailing on Cinderella with Istvan.
Cinderella is beautiful with everything you need and plenty of space. Istvan is just perfect! He knows the best places and is extremely competent which makes you feel totally safe. Istvan is very knowledgeable and an excellent host.
I will definitely book again and will be recommending without any hesitation whatsoever.

Josephine from UK

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