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.

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      EUR €70
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greece santorini oia white bell tower village seaside blue sky

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.
ACCOM: Overnight boat - 1

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.
ACCOM: Overnight boat - 1

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.
ACCOM: Overnight boat - 1

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.
ACCOM: Overnight boat - 2

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.
ACCOM: Overnight boat - 1

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.
ACCOM: Overnight boat - 1

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.
ACCOM: Overnight boat - 1

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.
ACCOM: Overnight boat - 1

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.