Before my Grecian adventure, I re-watched Shirley Valentine; Mamma Mia; Zorba the Greek and Captain Corelli's Mandolin. I couldn't believe that Greece would really look like that; the bright white buildings the clear blue sea, it seemed to good to be true. After a late evening arrival in Athens, and a delayed flight to Santorini I finally arrived on the island close to midnight. Diamantus from my guesthouse was waiting for me and we drove through the quiet island night, up and down hills. My little room in a white building with blue doors and shutters was just what I needed after two days of airports.

Awaking early to the sun shining over the arid island, I went for a walk alongside the bright white buildings on the cliff side overlooking the blue water surrounded by vineyards. It was just as I had pictured! (and just hat the movies promised) After a delicious breakfast with the owners of the guesthouse, I headed over to the marina to meet up with my group of fellow travellers. After introductions were made we jumped aboard Eva, our 50 foot yacht and home for the next ten days.

Our group of nine is in the capable hands of our skipper, he is leading us on Gap Adventure’s 10-day Greek Island Sailing. Sailing since he was 14, our skipper is fully capable of sailing Eva all by himself, although he was always willing to have a helping hand and teach anyone who was interested in learning. There is an itinerary set out in the brochure, but since it is a sailing trip itineraries do change. This sailboat is by no means luxury, but it has everything we need on board, including a small kitchen. The kitchen is great for making breakfasts and lunches, a great way to save money instead of eating out for all your meals. The berths are cozy and as a solo traveller I was matched up with another solo female traveller. The quarters were tight, but I slept on deck most nights under the amazing Mediterranean sky.

First stop Ios. White buildings with blue doors, shutters and roofs scatter the landscape all looking down over clear blue water. Around the port there are shops, a supermarket, a bakery and café selling amazing spanikopita, tzatziki and every kind of Greek dish you can imagine. The town is up the hill and every night the small winding streets are filled with people heading into tiny bars to dance all night.

Travelling by sailboat means you don’t have to find a place to stay when you arrive on each island, you are already unpacked and ready to go exploring (as opposed to the groups of people arriving by ferry). Another great thing about travelling by sailboat means you get to stop at some less visited islands, like our next stop Iraklia. We stopped there for one overnight on our way to Paros. We arrived late and found a tiny tavern full of locals and had a delicious meal of fresh, local sausage.

We sailed on to beautiful Paros, with it’s gorgeous winding alleys, seaside cafes and amazing beach. Next stop Naxos, one of the larger islands and a great place to rent a car or atv and go exploring. We drove along sheer cliffs to have a delicious local organic lunch in a valley in the middle of the island. On to Syros, the capital of the Cyclades. It is a real city and a great place to wander the streets and watch locals go about their daily lives.

Sailing through the turquoise waters we pulled into a small cove to go for a swim right off the boat. We continued on to Sifanos, a resort sort of town with a long beach and a lazy vibe. Another night sleeping on deck under the stars we moved on to Folegrandos. The town of Hora is a bus ride straight uphill from the marina. Hora is a small town full of twisting alleyways, which are easy to get lost in.

Early the next morning we sailed back Santorini and headed to the main town, Fira. Fira is bustling and a great place to buy souvenirs and watch as huge cruise ships arrive and hundreds of people unload - a vast difference from our small yacht docking in a private marina! A two and a half hour walk or short bus ride takes you to the idyllic town of Oia. Make sure you get there for the spectacular sunset.

Sailing the Cyclades is an amazing experience: island after island of idyllic beaches; brilliant bouganvilllia; tasty Ouzo; delicious food; great people and gorgeous scenery. The movies don’t lie. One elderly Greek woman on Santorini told me her island has more churches than houses, more water than wine and more donkeys than people. And that is just fine with me! Go see it for yourself!

Includes: accommodation, tour leader, transportation, local payment.

CDN$, per person. Land only. Other dates available, prices may vary, please contact us for details.

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