Cyclades Islands sailing holiday, Greece

A ten day sailing trip around the stunning Cyclades archipelago on board a top yacht. An odyssey through the lands of the gods.
Santorini Ios Amorgos Naxos Small Cyclades Syros Mykonos Sifnos Folegandros
£1525To£1640excluding flights
10 Days
More info
In addition to the listed price, this trip also requires payment in counrty of a compulsory Trip Kitty of approx.
EUR 80
Make enquiry

Description of Cyclades Islands sailing holiday, Greece

With many Cyclades Islands holidays a week long, this ten day odyssey gives us more time to do a full circuit starting and ending on the stunning island of Santorini. This is time to really bliss out on the Mediterranean but also enjoy some time helping out on deck, learning some sailing skills and really letting the wind flow through your hair.

We also have plenty of time on the islands that we visit where you will always find something to appeal, be it blissing out on a remote beach, hiking up to an ancient monastery or eating delicious local food. On Santorini, for example, which is actually a small volcanic archipelago, you can hike to its volcanic caldera or seek out Venetian settlements and ancient castles tucked into some of its many beauty spots. Or fall in love with Amorgos, where the famous Luc Besson film, The Big Blue, was shot, which you can experience at the likes of Paradisi Beach.

Sail in and out of the real big blue through the Small Cyclades and choose which one to anchor at with your skipper, although they are all so stunning, it is like being a child in a sweet shop. Naxos is hiking nirvana, up to ancient villages like Kastro, or even higher up to the Cyclades’ highest peak, Vas, at 1004m.

After a bit of livelier time on Mykonos, although there are plenty of quiet spots on this famous party island too, your last few days of this most serene of circuits takes in the Western Cyclades islands of Sifnos and Folegandros. Less visited than many of the other Cyclades, you can really seek idyllic island spots here, such as on Sifnos’ 100km of walking trails through its protected Natura 2000 landscapes.

Sailing specifics :

This is a real sailing adventure on a monohull yacht between 54-56 ft. We may opt for a smaller one if group size is best suited to that. Sleeping eleven travellers, there are 2 double cabins, 2 twin cabins and one triple cabin. All bathrooms are shared, with five in total. Rooms are allocated on arrival by the skipper and can’t be booked in advance, and solo travellers will be allocated a cabin with a fellow traveller of the same gender. In some cases, this may mean sharing a double mattress, so be prepared for close quarters, as is typical on a real sailing boat.

Similarly, there is an ‘all hands on deck’ approach to our sailing trips, although beginners are more than welcome, just swot up on your knots and terminology a little before heading off. There is minimal electricity, so this is not a hairdryer type holiday (the wind is free) and there is no Wi-Fi on board.


Price information

£1525To£1640excluding flights
In addition to the listed price, this trip also requires payment in counrty of a compulsory Trip Kitty of approx.
EUR 80
Make enquiry

Check dates, prices & availability

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1 Reviews of Cyclades Islands sailing holiday, Greece

5 out of 5 stars

Reviewed on 13 Aug 2017 by

1. What was the most memorable or exciting part of your holiday?

Sailing and learn a bit on how to do it

2. What tips would you give other travellers booking this holiday?

Try to build a nice team spirit with your co-travellers

3. Did you feel that your holiday benefited local people, reduced environmental impacts or supported conservation?

We tried to do so

4. Finally, how would you rate your holiday overall?

I would give it an 8 or 9 over 10 (I am very demanding) ;)

Responsible Travel

As the pioneers of responsible tourism, we've screened this (and every) holiday so that you can travel knowing it will help support the places and people that you visit, and the planet. Read how below.


As a global tour operator, we are committed to operating every one of our trips in a way that respects and benefits local people, their culture and economy, while minimising our impact on the natural environment.

You will travel in a small group, with a maximum of eight passengers on board a 50ft yacht, but if there are fewer passengers then we will use a smaller yacht. Bathrooms are shared and although there is hot water, we encourage passengers to use it carefully. Toilets are usually operated by hand-pumps and we have recycling arrangements on-board.

Weather permitting, we use the power of the wind to sail the boat as much as possible which means that we have less impact on the environment than if travelling by other modes of transport. When on land, you will mostly hike or walk although you may choose to take excursions by car or by public bus on Naxos and Syros.

As a tour company, our responsibilities don’t stop when our tours end. In 2002, we established a charitable foundation so that our passengers and staff could support grassroots community projects around the world. To date, it has raised over £2million for over 75 projects involved with health care, education, human rights, child welfare, sustainable development, and environmental and wildlife protection. We match every donation made by passengers and pay the administration costs, so every penny that is donated goes to a good cause.


We travel in small groups and wherever possible we use local transport, stay in locally-owned accommodation or homestays, eat at authentic local restaurants, support traditional artisans and small-scale businesses, and provide opportunities for travellers to interact with local people.

On this sailing adventure you will visit some well-known islands and some that are more off-the-beaten-track where the income from tourists is very welcome. For example, the island of Sifnos which is known for its high-quality ceramics which you may wish to browse or purchase. We can also sample local seafood in one of the waterfront tavernas, explore the terraced olive groves and visit the Museum of Popular Art.

Neighbouring Folegandros is also a spectacular but less well-known island, where we can visit small, family-run tavernas and hike to the Church of the Panagia for a stunning sunset vista. As part of our responsible travel guidance to passengers, we encourage you to dress respectfully if you wish to enter this or any other church on our trip, by covering your shoulders.

Your boat will be skippered by an experienced sailor, who will also be your tour leader. Of course, the main criteria for our skippers is their sailing ability but where possible we try to provide local employment and we’re delighted to have local sailor, Georgios as a member of our crew.

During the trip, we shop for local produce for our breakfasts and lunches, which the whole group will prepare and eat together on board the boat. In the evenings, we avoid the more touristic restaurants and seek out authentic, often family-run places so that we can support the local economy.

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