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No.72 Sailing in the Cyclades Islands

The first time I saw the Aegean Sea, in 2012, it was from the deck of a Blue Star ferry heading from Pireaus, the port of Athens, to Paros, one of the Cyclades Islands. I had spent many happy hours of my childhood sailing and swimming in rivers and bays on the east coast of the U.S., but I had never seen water that color — pure blue. From that moment, I knew I would someday go sailing in the Greek Islands.

In June 2015, I made my wish come true. I spent a week on the Rafaella, a 40-foot Oceanis sailboat, with my sister and Rafaella’s owner and skipper, Antonis Biskentzis, sailing from Paroikia, the main port of Paros.

Cyclades Islands

Our first stop was the main port on Naxos, the largest of the Cyclades islands. The Paros-Naxos leg of our journey was the only time we had to contend with rough seas. We had to motor into a strong north wind, with the mainsail set for some stability. Nancy and I both got queasy, but we knew that soon things would calm down and we would get our sea-legs. And indeed, after that afternoon, we felt perfectly comfortable on board.

In Naxos Town, we visited the Venetian Museum and the Folk Art Museum, explored the alleyways and shops, and had dinner in a tavern by the marina. The next morning, Antonis took us to a bakery where we bought bread hot from a wood-fired oven.

From there, we sailed south along the coast of Naxos, and began our real adventures. Antonis offered us several possible itineraries (always subject to the weather, of course). We opted to explore the wild places and tiny ports of the Small Cyclades. We spent our days sailing, swimming, and walking on shore. We ate on board, or at wonderful tavernas that Antonis recommended. The best meal we had — and one of the best Greek meals I have had anywhere — was at the Taverna Venetsanos on Kato Koufonisi, an uninhabited island with the taverna, a little church and a lot of sheep.


Often, when we stopped for our morning or afternoon swim, we were the only people in sight, anchored in a cove of emerald and turquoise water surrounded by rocky slopes. It was a feast for the senses: the slowly changing play of light and color; the buzz of cicadas in the brush, the clank of goat-bells in the hills, the lapping of water and humming of wind around the boat; the smell of salt sea and wild thyme in bloom.


We spent our fifth night on board at the port of Irakleia, which has a little harbor, complete with sandy beach. When we arrived, we had a swim, then set off to walk along the coast road to the other village on the island. We ended up exploring the hilltop ruins of a Venetian castle instead. For our final night, after a beautiful sail from Irakleia, we anchored between Antiparos, the small island next to Paros, and Despotiko, an uninhabited island that is the site of an active archeological dig. In the morning, Antonis offered us the chance to visit the main port of Antiparos, a charming town that I had seen several times before. We chose instead to have one final swim from the boat. Even within sight of the “big city” of Paroikia, Antonis was able to take us to a deserted cove where we could enjoy our last hours of meditative solitude.


For a few days after the trip was over, we still felt the movement of the boat. Even now, when I have long since regained my land legs, I can bring back a sense of deep calm and happiness remembering our week on the Rafaella.


About the author: Karen G. Krueger practiced law in New York City for 25 years. She now teaches the Alexander Technique, a mind-body method for achieving greater poise and efficiency of movement and dealing with chronic pain and stress.

Here are some tips from Karen for your excursion to the Cyclades Islands:

Hiring a Boat: Many companies offer bare-boat and skippered charters in the Greek islands. Our skipper, whom I highly recommend, has his own small company, Greek Water Yachts, based in Paroikia, Paros ( Look for discounts for early booking.

Getting There: Olympic Airlines (now part of Aegean Airlines) has regular flights from Athens to Paros, and Blue Star Ferries, Aegean Speed Lines, Sea Jets and Hellenic Seaways run ferries between Pireaus and Paros.

Our Favorite Taverna: Taverna Venetsanos, Kato Koufonisi:

Keep in Mind: Life on a small sailboat is like camping in a van: the boat has water and electricity, but in limited supply outside of ports. Your showers will be short. When you use the head (the toilet), you have to pump it out afterwards. And forget about checking your e-mails every five minutes: you may not have wifi or even 4G, and in any case, you shouldn’t be looking at a screen when you are surrounded by such beauty!

Take care in choosing your traveling companions. You will be together in close quarters most of the time. And don’t hesitate to get to know your possible skipper before committing. Make sure you discuss your desires for the trip, how you want to spend your time, and what the skipper has to offer. Are you interested in wild places, solitude and quiet, as we were? Or do you want shopping, night life and beaches with umbrellas, drinks and water sports? It pays to make sure your group and your skipper are all in agreement, or are prepared for compromise.

Also, you should get clear on what your role is on the boat. Antonis was able to handle Rafaella by himself, but we also did some crewing at our own request.

Finally, be realistic in your expectations. Sailing is dependent on weather and wind. The itinerary you hope for may turn out to be impossible. Sometimes, to get where you want to go, you may have to motor or motor-sail. When you do sail, it may be calm, exhilarating or anything in between.

With the right preparation and mindset, you can have the trip of a lifetime.

Photography and story by Karen Krueger

Planning a trip to sale in Cyclades Islands? Here is the current weather and what to expect for the next few days.