The sight of a Santorini sunset can turn even the most hardened of souls into a romantic. Walk along the volcanic rim of the island past white villages that cling to plunging cliffs
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.
Why We Love This Adventure
- Sail across the Aegean Sea on a yacht and island hop through the picture-postcard Cyclades. Swim off the side of the boat and let the waves rock you to sleep each night
- Feast on fresh seafood at a sleepy waterfront taverna in the Small Cyclades islands, far away from tourists and the rest of the world
- Step back in time among the Venetian architecture of Naxos and learn about present-day rural life with a daytrip to a country village
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.
Please make an enquiry and we'll send you the full itinerary for each day including meals, activities, travel and accommodation.
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.
PriceFrom GBP £1212.00
For the full list of included activities please make an enquiry and we’ll send full details over to you.
What's Not included
Please request full details
Trip Duration10 days
Start LocationSantorini, Greece
End LocationSantorini, Greece
Average Group SizeBetween 1 and 11
Overnight boat (9 nights)
No meals are included ion this tour
Monohull sailing yacht
This Trip is Suitable For
This trip has a physical rating by the operator of 2 out of 5. Get in touch to find out more about what this means and what to expect. This is a sailing adventure but it’s more about exploration than hands-on sailing (from you) or sail training.
For the full trip notes please make an enquiry and we’ll send them right away to help you decide if this is the perfect trip for you.
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.
Frequently Asked QuestionsWill I get sea sick?
As the majority of this trip takes place on a sailing boat, you’ll need to feel comfortable with moving about the vessel, including the use of stairs. With that said, sea legs come naturally to some but not so much for others. Your friendly crew will be able to help with the effects of sea sickness if needed.What are the sleeping arrangements?
This is an adventure on board a real yacht, which means living spaces, cabins, bathrooms and showers need to be shared with other passengers. Sleeping quarters can be quite compact, but you will be spending the majority of your time above board in the open air.Do I need sailing experience to take part?
No. This trip is more about using a sailboat as a base camp to explore the islands rather than a hands on sailing adventure or sail training voyage – speak to us if you’re looking for a different style of sailing trip.
Dates & Availability
- 12 May 2018 – 21 May 2018
- 22 May 2018 – 31 May 2018
- 01 Jun 2018 – 10 Jun 2018
- 11 Jun 2018 – 20 Jun 2018
- 21 Jun 2018 – 10 Jul 2018
- 11 Jul 2018 – 20 Jul 2018
- 21 Jul 2018 – 30 Jul 2018
- 31 Jul 2018 – 09 Aug 2018
- 10 Aug 2018 – 19 Aug 2018
- 20 Aug 2018 – 29 Aug 2018
- 30 Aug 2018 – 08 Sep 2018
- 09 Sep 2018 – 18 Sep 2018
- 19 Sep 2018 – 28 Feb 2018
- 29 Sep 2018 – 08 Oct 2018
This trip can be tailor made for your perfect travel dates. Please make a booking enquiry for more information.
We love this operator for the freedom and flexibility they give travellers to get off the tourist trails and really experience local cultures. Their style of small group travel is perfect for solo travellers, couples or small groups of friends and their grassroots style of travel seeks to have a positive impact on the communities they visit.
They use local leaders, local accommodation & transport and support local community projects, ensuring sustainability is at the centre of everything they do.
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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