Cyclades sailing & walking holiday in Greece

“Our only week long holiday of island hopping, hiking and all round Hellenic hedonism in the Cyclades archipelago of Greece.”

Highlights

Six days sailing the Cyclades | Naxos | Temple of Apollo | Iraklia Island | Cave of St. John | Amorgos Island | Koufonisia Islands | Paros Island

Description of Cyclades sailing & walking holiday in Greece

This holiday is a perfect meze for those who are looking for a Cyclades sailing holiday but with a chance to go walking on some of the small, non-touristy Greek Islands too. For some it’s a sailing holiday with a few treks thrown in, but also ticks beautiful boxes for those seeking remote walking holidays in Greece, with sailing an added bonus.

In a week you can discover the unique nature and landscapes of islands such as the Cyclades’ highest peak, Zas, on Naxos or the ancient paths of Amorgos or Iraklia, with their unique flora and fauna.

Cyclades sailing and walking holidays also means plenty of swimming in between islands, seeking out uninhabited idylls with virgin beaches, enjoying a beach barbecue or anchoring up in time for an evening stroll to discover picturesque villages and Venetian and ancient settlements, or take in another breathtaking, sunset view over the Aegean from the island’s peak. Then waking up, sailing to another island and starting all over again.

Day-by-day experiences

Day 1:Our sailing odyssey starts on the Cyclades island of Naxos. After a quick briefing, we will go for an evening stroll around the old town and the Venetian castle, followed by a short walk to the Temple of Apollo to watch the sunset over the Aegean. We'll end the day with dinner at one of our favourite tavernas on the island.
Day 2:We'll start with a morning hike from the idyllic island village of Filoti, which leads up to the highest peak on the Cyclades Islands, Mount Zas. From here you can take in the turquoise waters you are about to set sail on, looking out to the West and Small Cyclades Islands. The perfect picnic spot too. After our hike back down to shore, we board our sailing yacht and head to one more corner of Naxos, the remote bay of Kalando in the South of Naxos, for a beach barbecue and evening swim.
Day 3:Keen swimmers might want one more morning dip in Kalando Bay before finally saying farewell to Naxos, and sailing to the tiny island of Iraklia. With several walking tracks, one that we recommend is from the town of Panayia to the ancient cave of St. John, the largest cave in the Cyclades, famous for its fine collection of stalactites. This walk also includes a wonderful elevated spot to enjoy the sunset, before descending back down to the main village of Panayia to a top taverna that is also the village bakery.
Day 4:Today’s island is Amorgos, a mountainous treat, although water lovers will find the stop off en route, at the deserted island of Antikeri, hard to beat, with some of the Cyclades’ most tranquil swimming and snorkeling. The Amorgos fishing port of Aegiali is also a dreamy place to sleep, after a short hike to the village of Tholaria, where meze, music and much fun awaits.
Day 5:Today is our day to discover the rest of Amorgos’ cultural and natural treats, starting in the village of Langada, following tiny pathways up to the church of St. Theologos, glistening white on an elevated rocky outcrop. After a picnic lunch, we continue up to the north east of the island, a beautiful region and protected Natura 2000 reserve, thanks to its unique island ecosystem. From here, a dramatic sea view walk takes us towards Stavros, with stunning clifftop views, with a final descent to Aegiali’s beautiful beaches for the usual end of day swim and supper.
Day 6:Our next island to be hopped is Kato Koufonisi. Anchoring in a quiet bay of Nero, you can walk around this tiny island before being hosted for supper at the taverna of the only family resident here. Producing all their fruits and vegetables and owning their own animals, this is slow food and slow travel at its finest.
Day 7:Our final sailing trip is to the island of Paros, where we moor at the pretty fishing port of Piso Livadi. One of our favourite walks is saved for our last day of the trip, it is the Venetian path from the old capital of Paros, the village of Lefkes to the village of Prodromos, both traditionally Cycladic boasting tiny white houses and chapels and narrow alleys adorned with beautiful flowers. Our farewell dinner is at another of our top tavernas, accompanied by some traditional Greek music.

Travel Team

If you'd like to chat about this holiday or need help finding one we're very happy to help. The Travel Team.

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Check dates

2021: 31 Jul, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 Oct
Our top tip:
Shoe packing dilemmas? Think closed hiking boots, flip flops and lots of barefoot. And pack lightly.
Trip type:
Small group , max. 6 people.
Activity level:
Easy/moderate.
Accomm:
Double/twin cabins. Communal bathrooms.
Included:
Accommodation, guided walks, breakfasts, fresh water, port fees, snorkeling equipment.
Meals:
Buy picnics at local shops and dine out in evenings. Budget £12 for dinner and wine.
Solos:
Solo travellers welcome. Surcharge for own cabin.
Diet:
We cater for both vegetarians and vegans.
Vouchers
Accepted

Responsible tourism

As the pioneers of responsible tourism, we screen every trip so you can travel knowing your holiday will help support conservation and local people.

Environment
The sailing & walking week has an eco focus. It informs our guests about the endemic species that they will encounter while sailing & walking around Greece. We'll show our guests a couple of presentations on the local widlife that will help them appreciate what the see. It’s essential that you appreciate and understand the beings that you come face to face with. If you understand them, you know where to find them, how to approach them in order not to scare them and disrupt their life and how to observe their behaviours.

In general with all our trips, we’re trying through our activities to encourage travellers to approach places they visits with greater understanding and respect. A few of our activities and actions related to wildlife:

- We organise wildlife tours which combine sailing and discovering endemic species. Under the guidance of our experienced biologist, people are introduced to tens of endemic species, both from the animal and plant kingdoms which exist only in this small corner of the globe. Guests leave with a different approach towards wildlife and aware of the dangers they face and how to minimise them.
- We organise visits at the two national marine parks in Greece, in Zakynthos and Alonisos, where the two most important NGOs for the protection of the loggerhead turtle Caretta caretta and the Mediterranean monk seal Monachus monachus are based. Our guests are briefed on their work and how they can get involved and support them.
- We watch and monitor dolphins & other cetaceans by far away without disturbing them, adhering to the ACCOBAMS guidelines for commercial cetacean-watching activities in the Mediterranean Sea.

When our sailing boat, is not chartered, we sail around cleaning beaches, recycling or giving a helping hand to researchers and organisations in their efforts to collect data in order to study and protect the environment and wildlife.

By including in our itineraries and taking our guests to remote or underdeveloped islands [such as Kinaros (population: 2 people), Levitha, Iraklia and Anafi (population: under 100 people)] we aim to distribute economic benefits to those places that are hard to get to due to lack of frequent ferries or that are unreachable without a sailing boat or similar means.

- By recommending the purchase of products from the local agricultural co-operatives which function in many islands
- By advising our guests to taste the local cuisine in local taverns and get a taste of the local culture and avoid global restaurant chains
- By recommending rooms & apartments that we have carefully selected that are run by local people, not generic hotel chains.
Community

The Impacts of this Trip

We include in all our itineraries and take our guests to remote or underdeveloped islands [such as Kinaros (population: 2 people), Levitha, Iraklia and Anafi (population: under 100 people)] as we aim to distribute economic benefits to those places that are harder to get to due to the lack of frequent ferries or because they are unreachable without a sailing boat or similar means.

We encourage our guests to visit and try the local cuisine and purchase local goods wherever we go in order to get a taste of the local culture and also support the local community. More specifically:

- We recommend our guests the purchase of products from the local agricultural co-operatives which operate in many islands,
- We advise our guests to taste the local cuisine in local taverns and get a taste of the local culture and avoid global restaurant chains,
- We recommend our guests to stay in rooms & apartments that we have carefully selected that are run by local people, not generic hotel chains.

Our base has become the island of Syros where most of the maintenance work is carried out. We employ locals for all the jobs concerning the boat. We buy materials for the maintenance of the boat from local shops.

Climate

15 Reviews of Cyclades sailing & walking holiday in Greece

4.5 out of 5 stars
SHOW
6
7
2
0
0

Reviewed on 20 Sep 2019 by

Excellent! I would strongly recommend this to anyone who enjoys moderate walking in great landscapes, with opportunities to swim most days, the company of like-minded folk and with supportive and fun local guides. Read full review

Reviewed on 15 Sep 2019 by

Fantastic guides Annie & Dimitria who showed so much care, thoughtfulness & took us on fantastic walks. Read full review

Reviewed on 28 Jun 2019 by

While hiking, we were thrilled with the landscape and felt very privileged to be in it, rather than just driving by. Each hike on the six islands we visited was different from the one before. Read full review

Reviewed on 27 Jun 2018 by

Excellent. Annie and Sotiris were excellent hosts and ensured that the trip ran smoothly. On the one day that the wind was too strong for sailing, we had a busy sightseeing day instead. Read full review

Reviewed on 08 Oct 2018 by

The first 2 days of the trip were glorious! Beautiful less visited islands & fishing villages. Our walking guide Yannis & Captain Soteris made sure we visited areas & restaurants off the beaten path, making for an authentic experience. Read full review

Reviewed on 24 Oct 2017 by

Fantastic! Very memorable. Something I'd want to repeat. Read full review

Reviewed on 17 Sep 2017 by

There were many 'wow' factors - the weather, the unspoiled islands, the clear unpolluted waters we sailed and swam in, stunning walks/hikes learning the history of the Cyclades, the friendly locals and the great food. Read full review

Reviewed on 27 Oct 2015 by

Excellent, forgot how blue and clear the water is, and it was great to get to the smaller islands were people lived their everyday lives, highly recommend this holiday. Read full review

Reviewed on 06 Oct 2015 by

We would rate our vacation as Excellent. Our guide was wonderful, taking us on little-travelled paths and educating us along the way with interesting information not found in guidebooks Read full review

Reviewed on 21 Jul 2015 by

Excellent, thanks so much. We really enjoyed the trip, the company, the places we visited and the people we met. Read full review

Reviewed on 28 Apr 2013 by

10 out of 10 based on the companionship, weather, knowledge and sheer good fun that was had by both of us during this holiday. Read full review

Reviewed on 31 Oct 2012 by

First-rate. A great and memorable experience. It also introduced us well to the people of these smaller islands and their way of life. Happy to recommend strongly. Read full review

Reviewed on 21 Aug 2012 by

One night we went swimming off the boat and saw stars in the water. It wasn't a reflection of the sky but light that tiny sea creatures gave out when we touched them. When we came out of the water it seemed that we were sparkling too!...A rare and very special holiday! Read full review

Reviewed on 26 Oct 2012 by

I had a great holiday, I'd rate it very highly. I met some interesting people, saw some beautiful sights and had a great time learning to sail, walking up mountains and relaxing on deck. Read full review

Reviewed on 15 Oct 2012 by

Great fun, we had a good group and Annie makes the whole thing work. We met really nice local people who opened up simply to serve us food even though the season was over. Read full review

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