Minor Cyclades Islands Sailing

Sailing boat cruise on the Minor Cyclades Islands - Sailing the Cyclades

Rent a yacht in Cyclades with a skipper


Islands hopping: Paros – Naxos(or Paros – Piso Livadi) – Kalando – Koufonisia – Amorgos – Iraklia – Antiparos – Paros

Suggested for: Couples and friends sailing, Sailing for families, honeymoonnaturists sailing

Max sailing time per day: 3-4 hours

Miles in total: 110-120

  • this is our favorite route for your chartered sailboat trip with skipper and is working pretty well especially when the meltemi‘s presence is remarkable
  • it is a combination of some busy islands, like Naxos, with some tiny, quite places, where you will meet the real Cyclades
  • the sailing legs are not very long, ideal for the beginners or for families with kids, leaving you plenty of time to enjoy your sailing cruise, swimming and relaxing under the summer sun
  • the early arrivals at the islands give you the opportunity to walk or drive around in order to explore the unique scenery

Sailing the minor Cyclades interactive map

Suggested route day by day

Day #1

Meet your skipper at the Marina cafe at 11:00 and board the sailboat. After the briefing concerning your trip, set sail around Paros for our first destination, Naxos. Depending on the weather conditions its going to take us 3-4 hours sailing trip. Naxos is one of the biggest islands of the Cyclades with great interest and many sightseeing. Don’t miss the sunset at the ancient temple of Apollo, just a few meters away from the marina. Grilled octopus with “ouzo” is a “must” here.

Day #2

Today we are going to sail south following the west coast of Naxos ending up at the most south of the island, at Kalando bay. In the mid way your sailboat will stop at a nice anchorage,Roga, for swimming and lunch. Kalando is a special place. There is a safe port for the yacht but not a village. It’s an isolated area with a long sandy beach and many kilometers of trails by the seaside, ideal for hiking in the pure nature. For dinner a primitive kiosk operated by a local shepherd offers BBQ only with local products. Don’t expect luxuries here. For sure it’s going to be your favorite place at the end.

Day #3

Set sail from Kalando heading for Koufonisi. A short stop before our final destination , at a wonderful spot, called Rina, where you can swim inside a sea cave. Amazing colors everywhere. Koufonisi is further the most beautiful of the small Cyclades islands with many sandy beaches all around. Rent a bicycle and visit all of them. Dinner at “Captain Nicolas” place is out of any kind of negotiation as well as a frozen mojito at the wind mill bar just above the marina.

Day #4

If we have strong wind today we recommend to stay in the area visiting with the sailing yacht the nearby island of Kato Koufonisi and swim in crystal clear waters, snorkeling or go hiking around. The area is very protected from big waves because the huge island of Naxos to the north blocks the wind in order to make our life on board more comfortable. In the afternoon we will return at the same marina at Pano Koufonisi. Alternative in case that the weather permits us we will continue our sailing trip to Amorgos, the island of the “Big blue” movie. Rent a car or a bike here to explore the wild beauty of this heaven. Visit the famous monastery with the breath taken view from its balcony and try “rakomelo”, the local alcoholic drink. Dinner at “Xilokeratidi” is going to be a memorable romantic event by the sea side.

Day #5

Iraklia is another island of the “Small Cyclades” which is worth to be visited especially for those who want to experience tiny, quiet, cute and isolated places, representative of the Greek spirit. So after a short stop for swimming at Antikeros on our way from Amorgos to Iraklia we will end up at the picturesque port of the island. Here you can swim to the nearby beach, diving from the yacht and hiking around enjoying the pure nature. Dinner at Iraklia means fresh fishes and the local tavernas more hospitable than anywhere else are ready to fulfill your expectations.

Day #6

Antiparos is the last island of our cruise. After a 4-5 hours sailing trip and of course after the oblate stop for lunch and swimming we will end up at Antiparos late in the afternoon. Wandering around the small streets of the beautiful village, have dinner in one of the hundreds restaurants and continue with a drink at one of the locals bars. Night life here, especially at high season is a must for everyone.

Day #7

We strongly recommend you before setting sail for our final destination, to visit the cave of Antiparos. Buses are operating just 100 meters away from the yacht. On your return on board we will leave immediately for a nice anchorage at a small island north of Antiparos with crystal clear water. The afternoon has already come as well as the farewell time at Paros port.


Contact and booking

Make your introductory reservation request to Greek Water Yachts for your skippered Greek sailboat rental, sending as an email at greekwateryachtsinfo@gmail.com. Greek Water Yachts team will respond within 24-48 hours.


Check out our questions and answers section about common questions concerning your sailing trip to the Greek islands with captain.

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Apostolos V

Contact person
Desktop site
Greek Water Yachts
Paroikia Paros

Phone: +306932299490