Sail the Mediterranean waters around Greece's Cyclades Islands

Give in to dreams of sailing the Greek Islands on this seafaring adventure around the renowned Cyclades Islands. Bliss out on Mediterranean waters, swim in turquoise seas, explore ancient towns and delight in fresh Greek food and culture. From laidback non-touristy islands like Small Cyclades to the vibrant holiday mecca of Mykonos, all holiday bases are covered on this eight-day sailing odyssey.

Santorini, Greece
Santorini, Greece
Physical rating
Cultural rating
Min 12
Group size
Min 1 Max 8
Carbon offset
0kg pp per trip


  • Admire cascading bougainvilleas


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.
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.
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.
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.
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.
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.
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.
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.
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.
View trip notes to read full itinerary


9 breakfasts, 9 lunches
Overnight boat (9 nights)


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Important notes

This trip starts on Day 1 in Santorini at 11am and finishes on day 10 in Santorini at aprrox 11am depending on weather conditions.

Trip notes

Want an in-depth insight into this trip? Your trip notes provide a detailed itinerary, visa info, how to get to your hotel, what’s included - pretty much everything you need to know about this adventure and more.

View trip notes


Our Sail Greece - Cyclades Islands trips score an average of 4.81 out of 5 based on 47 reviews in the last year.

Greece Sailing Adventure - Cyclades Islands , September 2015

Greece Sailing Adventure - Cyclades Islands , September 2015