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Sail Greece - Cyclades Islands Itinerary
See the best of the Cyclades Islands on this Greece sailing adventure. Take to the glorious Mediterranean Sea and explore these famous Greek Islands, finding out firsthand what all the fuss is about.
Trip Price tool tip
USD $1,760CAD $1,780AUD $1,850EUR €1,285GBP £1,105NZD $2,195ZAR R16,840CHF FR1,585
Kitty tool tipEUR €80
Total price tool tip
USD $1,874*CAD $1,891*AUD $1,905*EUR €1,365*GBP £1,174*NZD $2,355*ZAR R17,637*CHF FR1,675**
Day 1 Santorini/Ios
Launch the Cyclades sailing adventure from the sands of Santorini, feeling the rush of the ocean breeze as the boat sails for Ios. Upon arrival, be charmed by this exciting island that is both a haven for party-goers from all over Europe and a true historic gem. Then, when the day is done, relax on deck and appreciate the serenity of life atop the water.
Day 2 Amorgos
Cast away to the mountainous shores of Amorgos, an ancient city with a colourful past and classic Greek architecture. In free time, perhaps admire cultural relics housed in Gavros Tower before settling into a waterside restaurant at Katapola.
Day 3 Small Cyclades
Journey across the glistening Aegean Sea and drop anchor on this lightly populated island. With a much slower pace than its more touristy cousins nearby, Small Cyclades is the ideal place to truly unwind, kick back on the boat and take in this beatific region.
Days 4-5 Naxos
After another morning of exhilarating sailing, land on charismatic Naxos. Admire medieval buildings on a visit to the Venetian Kastro, check out an old Romanesque church and perhaps make acquaintance with locals on a country excursion. While here, sample a host of sultry beaches and a radiant nightlife.
Day 6 Syros
Discover authentic island life on a visit to Syros. Explore narrow stairwells and whitewashed squares that open out onto breathtaking coastal vistas. See the stone-walled village of Ano Syros and sample classic Greek fare in Ermoupolis.
Day 7 Mykonos
Travel to one of the most enigmatic of all the Greek Islands, Mykonos, and uncover a glorious calamity of sun, fun and history. After a day spent exploring, head down to Little Venice and watch a magical sunset from a restaurant balcony.
Day 8 Sifnos
On the ancient island of Sifnos, enjoy floating atop the blue waters off Kamares, mingle with locals and travellers alike in Apollonia and perhaps get a little culture at the Museum of Popular Art.
Day 9 Folegandros
Set sail for the bold cliffs and striking landscapes of Folegandros. While wandering about this scenic island, take in the scent of fresh bougainvilleas that line the walled pathways and maybe head up to the hillside church in time for sunset.
Day 10 Santorini
The sailing journey comes full circle back on the volcanic beaches of Santorini. If time permits, stay a little longer here to soak up more of the cultural, social and gastronomic delights on offer.
Sail Greece - Cyclades Islands Reviews
Our Sail Greece - Cyclades Islands trips score an average of 4.74 out of 5 based on 19 reviews in the last year.
Sail Greece - Cyclades Islands, June 2014
Kostas has a sunny nature and was fun to be with- he was caring, sociable and played the best music on board!! When berthing at port he was very professional and safety was always of paramount importance. He was a joy!
Review submitted 27/06/2014
Sail Greece - Cyclades Islands, June 2014
The best trip I've ever had. It was so much fun. Absolutely loved it. Kostas absolutely made this trip. He was so thoughtful, helpful and so much fun. He did an amazing job with a very different group of people, some who really had no idea about the realities of a sailing trip and got seasick and were not at all used to the confined spaces of a yacht. He handled difficulties with them brilliantly, doing everything he could to make them comfortable, and the sailing smooth. He is just the most amazing person - genuinely kind and loving and such a character. We all had the best time and were so sad to leave him. He is an expert sailor and a fantastic tour guide and we had many great fun times on land and sea with him. I loved the sailing and Kostas was very patient about teaching me and the others who wanted to take part all about how to sail, anchor etc. I absolutely love Greek people - they are so down to earth and fun - a bit like Aussies maybe and Kostas is the best of them all. I feel like we have made life long friends from this trip and cannot recommend it, or Kostas, highly enough. Kostas was so entertaining that we all laughed until we cried a number of times and our boat always seemed like the happiest, funnest boat in every port, as we were always dancing and singing and having fun with our great skipper. You couldn't pay for advertising like that and we always felt sorry for the people with other companies like Sail Greece who never seemed to be having half as much fun as us. I wouldn't sail in Greece with any other skipper and neither, I think, would my fellow sailors. He is number one in my books and a friend for life.
Review submitted 22/06/2014
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