A few years ago, we decided with my partner to visit Paros and then try the adventure of a sailing holiday. Neither of us had any experience with sailing and so we decided to rent a boat with a captain.

The choice of Paros to start our sailing vacations was ideal because is within close distance of the other Cycladic islands. Other options we could have been the Ionian islands (such as Corfu and Ithaca) or some of the Greek islands of the Dodecanese, such as Rhodes and Kos.
But the abundance of tranquil villages, beautiful beaches and countless islands and rocky islands made our choice as easy as possible.

After some days on the island of Paros, the morning that we would start our private cruise had arrived. We have been around for the last time in the straits of Parikia, and the time has come to meet Antonis, our captain and our guide on this weekly trip.

The sailboat was easy to be found, a 40-foot monohull sailboat(unlike the catamaran) named Rafaella in excellent condition.
Our private trip to the Cyclades islands with the rich history and countless islands has just begun.
After shopping at the supermarket, fresh tomatoes, oregano, tuna capers, bread, toast and other basic everyday items, we started talking to Antonis about the choices we have.

blue lagoon paros antiparos

blue lagoon Antiparos

That night, on a Friday night in June, we anchored in a small bay, quiet and isolated near the island of Antiparos. The light shake of the boat and the quiet sea offered us the best nighttime sleep.

As the first rays of the sun reached through the portholes, Antonis was already awake and was preparing a simple morning with coffee and croissant. The air was south-east relatively strong, ideal to start off for the next trip to the island of Delos …

The trip to Delos was a 3-hour trip without any stops. Antonios, after half an hour, opened the sails and turned off the engine. The feeling of traveling only with sails was incredible. You only hear the boat sinking over the spume of the waves. The absolute calm. After a 3-hour trip, we arrived at the island of Delos.

sailing cruising delos


The islands of the Cyclades, which mean a circle, attribute their name to the way they are located around the island of Delos. Delos is now a UNESCO World Heritage Site and one of the most important archaeological sites in Greece dating back to the Bronze Age. Arched statuettes, mosaics depicting dolphins, phallic monuments to commemorate Dionysios, a dry lake where Apollo is said to have been born and a beautiful theater in the middle of the island. A very beautiful experience.

In the afternoon we started the short trip to the famous island of Mykonos. After we tied up to the organized marina, we took a taxi and headed for the city. Mykonos is indeed the tourist Mecca of Greece. Magnificently crafted up to the last detail, jewelry from the famous houses, but also beautiful beaches with a crowd of people. The truth is that the Mykonos environment has been a bit overwhelming in relation to the feeling we have so far gained from the quiet bays and the tranquility of the trip.

The next morning we began our trip to our next station in nearby Naxos, the largest of the Cycladic islands. The bay we anchored was tiny. With a fishing village as our background, it was the perfect place to take a dip in the crystal clear waters. To get there, the only way is to rent a sailboat. None of the cruise ships go to such places, perhaps the biggest advantage of chartering a sailboat.

naxos portara

Portara Naxos

In the afternoon we tied to the port of Naxos with its imposing Venetian castle. Here you will find the paradise of good and cheap cuisine. There are plenty of restaurants on the beach but also on the inland. Antonis suggested that we visit the castle and go to eat in a nearby village in Melanes. We tasted traditional dishes and perhaps the best pork we’ve ever eaten!

The next day after we got breakfast at Naxos beach, we started for our next station, an island that did not even mention the bulky travel guide of the Greek islands that I was carrying with me. The wild and rocky Donousa.

The largest settlement on the island is Stavros. It has a large clear beach, and many, for the size of the settlement, taverns. In addition, there is a small cafe under the trees with nice music and a cheap but hearty breakfast (and not only).

In addition to Stavros we visited the famous Kedros beach on foot. It is worthwhile to walk it day and night. In the morning for an archery and swim in its blue waters, where you can see with a mask in relatively shallow waters and the remains of a German warship from the Second World War, while in the evenings to have fun at the various parties at the coffee bar of the beach.

trip to donousa with a sailboat

no cars, no scooters, only sun and wind, Donousa. Only on foot

We loved Donousa so much so we decided to stay another day. The next day we followed the many paths with the 5 main routes. After our first stop on the beach of Kedros, we started for Livadi. In Livadi, we stopped and bathed in the stunning blue-green waters. This particular beach is a favorite nudist destination…

After we swam, we walked to the nearby and small beach of Phokio, which you will find following a small path that is on the left side of Livadi beach, as you look at the sea.

At noon we returned to the boat for a rest. Antonis suggested visiting Focospilia by the sailboat. “It is also worth taking a lot of dives here and see the unique blue natural lighting that the waters and rocks acquire in a few places”, he told us. The seabed was beautiful, the rocks above you where imposing and the long-lasting experiences unique. If you visit Focospilia always have a mask because it is a pity to go up there and not to see the toys that make the light under the water.

We spent the night in the anchor at Focospilia. The next morning we would start for Amorgos, the island of the “Big Blue” …

The next morning, Antonis decided that we could start the trip to Amorgos, even though the wind was strong. After 3 hours of sailing and motoring in big waves(and in my husband’s arms), we arrived at Katapola in Amorgos.
Amorgos has varied scenery, interesting walking terrain, archaeological sites all over the island, two noteworthy sightseeings  – the Byzantine Chosoviotissa monastery, hanging on 300m sea cliffs and locations that feature in Luc Besson’s 1988 cult film Le Grand Bleu (The Big Blue) and a broad system of waymarked paths utilizing the old donkey streets(monopatia). We started our climbing to the monastery of Chosoviotissa.

amorgos trip

view from the monastery

I can not describe the feeling as we went up to the monastery. An image I will never forget. In the evening we found a traditional taverna where you enjoy your coffee among the locals and visitors of the island, along with various snacks of delicious meatballs and real fried potatoes, fried eggs, sandwiches and fresh salads.

The next day we continued the trip with the sailboat. After the necessary break for diving and eating in a bay south of Naxos, and with the god of Poseidon on our side we arrived late at the evening in Antiparos. Tired of the long trip, we took a walk in the narrow streets of Antiparos. The next morning we visited the cave of Antiparos.

The cave extends to a depth exceeding 100 meters and overs an area of 5,600 m2. The Cave of Antiparos also boasts the oldest stalagmite in Europe, which is 45 million years old. Our trip was ending and on our last stop, we visit a cove in Antiparos for swimming. In the evening we have arrived in Parikia.

Generally, a journey that you will remember for a lifetime. Peace, nature, sea, salty, good food, great views and an experienced and friendly skipper. I would definitely do it again. I do not think I’ve ever had a better holiday.



writer of the travelogue sailing the cyclades