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sail greece

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Sail Greek Islands Adventure

Fulfill your fantasies of living like a Greek God or Goddess on this ten day sail greek island adventure.  Chart a course for the renowned Cyclades Islands and swim in the turquoise coloured seas, discover ancient towns, dive into fresh Greek food and bliss out on Mediterranean waters.

You’ll visit a wide variety of Greek Islands – from the vibrant getaway mecca of Mykonos to the laid back and off the beaten path islands like Small Cyclades. You’ll also visit the islands of Santorini, Amorgos, Naxos, Syros, Sifnos, Folegandros, and Santorini.


  • Floating along the brilliant blue waters off Kamares’s port
  • Exploring the ancient ruins of Amorgos
  • Tour the countryside of Naxos
  • Admire the cultural relics found in Gavros Tower
  • Sample fresh seafood and traditional Greek cuisine
  • Sink in to a gorgeous view of a Greek sunset from a hilltop church on the deck of the yacht.

Each day is packed with options to make this the sailing adventure of your dreams.  At each island stop you’ll have the option to to explore a wide variety of cultural destinations like the Venetian Kastro, Roman churches, the stone-walled village of Ano Syros, or simply sit yourself down at a small local cafe and strike up a conversation with the locals.

If exploration doesn’t suit you on any particular day, you can always head straight for the beaches as soon as you drop anchor.  There is no better way to spend time than relaxing on beautiful beaches with a good book in one hand and a refreshing drink in the other. What others only dream of, you’ll actually be doing.

Life on board the yacht is just as exciting as off.  Group size is always small, up to eight people, and as such everyone pitches in to help with cooking and cleaning up.  In this way, your sailing vessel comes to feel more like home away from home and adds to the sense of exploration – helping to remove you from feeling so much like a tourist.  It’s an idyllic life at sea.

The Greek Islands are simultaneously charming, relaxing, invigorating, and fun.  You find your own personal balance in order to sink in to the perfect adventure getaway to these picturesque islands.  Enquire today.



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.

More Details

This trip starts on Day 1 in Santorini at 11am.

Summer temperatures can reach up to 40 degrees Celsius, which can be uncomfortable for those not used to the heat. Please consider the time of the year you wish to travel and your suitability to that season.

The minimum age on this trip is 15. Please note that triple cabins are not available. If travelling with a child, the child will need to share with one of the adults, and the other adult will share with another adult passenger, or pay a single supplement.

Please provide full passport details at time of booking including exact name as per passport, date of birth, nationality, issue and expiry dates as these are essential for booking services on this trip.

Overnight boat (9 nts)
This trip is accommodated entirely on board a yacht of between 48ft to 52ft. A typical yacht for 8 travellers is equipped with 4 twin/double share cabins, 2/3 shared bathrooms and 2 showers.

Our boats are real yachts and this is a real sailing trip. Yachts are designed to keep sleeping areas to the absolute minimum of space, while maximising common areas as much as possible. Smaller yachts will be used for smaller groups sizes.

Rooms are allocated on arrival by our skipper according to group composition, which means it is not possible to reserve or guarantee any specific berth or cabin. Single passengers will be paired up with another passenger of the same gender, this may mean sharing a double cabin with a double mattress.

Everyone including the skipper shares the bathrooms on board.

While not everyone may feel entirely comfortable living in such close quarters, those who are looking to revel in the adventure and exhilaration of an authentic sailing trip usually find any discomfort from cramped living conditions is more than made up for by the whole experience.

Please note that the majority of our sailing trips start and/or finish at a marina or port. If you have pre-booked any additional accommodation through us, you will need to make your own way to the joining point on day 1 and from the finish point on the final day. We do not provide transfers between hotels and the port/marina. Please check the joining and finish point information in the trip notes for details.

Dates & Rates

Departure dates:
  • Tue 23 May 2017 – Thu 1 Jun 2017
  • Fri 2 Jun 2017 – Sun 11 Jun 2017
  • Mon 12 Jun 2017 – Wed 21 Jun 2017
  • Thu 22 Jun 2017 – Sat 1 Jul 2017
  • Sun 2 Jul 2017 – Tue 11 Jul 2017
  • Wed 12 Jul 2017 – Fri 21 Jul 2017
  • Sat 22 Jul 2017 – Mon 31 Jul 2017
  • Tue 1 Aug 2017 – Thu 10 Aug 2017
  • Fri 11 Aug 2017 – Sun 20 Aug 2017
  • Mon 21 Aug 2017 – Wed 30 Aug 2017
  • Thu 31 Aug 2017 – Sat 9 Sep 2017
  •  Sun 10 Sep 2017 – Tue 19 Sep 2017
  • Wed 20 Sep 2017 – Fri 29 Sep 2017
  • Sat 30 Sep 2017 – Mon 9 Oct 2017
  • Sat 12 May 2018 – Mon 21 May 2018
  • Tue 22 May 2018 – Thu 31 May 2018
  • Fri 1 Jun 2018 – Sun 10 Jun 2018
  • Mon 11 Jun 2018 – Wed 20 Jun 2018
  • Thu 21 Jun 2018 – Sat 30 Jun 2018
  • Sun 1 Jul 2018 – Tue 10 Jul 2018
Prices: starting from approx 721 GBP (vary by date).


  • Meals
    No meals are included on this tour
  • Transport
  • Accommodation
    Overnight boat (9 nights)


We love this operator for the freedom and flexibility they give travellers to get off the tourist trails and really experience local cultures. Their grassroots style of travel ensures the impact on the communities they visit is minimised. They use local leaders, local accommodation & transport and support local community projects, ensuring sustainability is at the centre of everything they do.

New sailing itineraries in Burma and the Caribbean have been created along with delicious food adventures in Peru, Cambodia and Italy and inspiring new trekking trips in Morocco and Nepal. This operator is committed to operating in a responsible manner, incorporating the principles of sustainable development in the way they provide travellers with real life experiences. However, these values are more than just words on a page; they are ingrained in the culture and daily operations of every office and tour.

In addition, they expect their staff and travellers to demonstrate the principles of responsible travel – respecting people, cultures and local environments; in the distribution of wealth; in good will and cross-cultural sharing; and in contributing to sustainable development. 

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