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

6 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 itinerary

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.

Hello. If you'd like to chat about this holiday or need help finding one we're very happy to help. Rosy & team.

01273 823 700

Check dates

2017: 29 Apr, 6 May, 13 May, 20 May, 27 May, 3 Jun, 10 Jun, 17 Jun, 24 Jun, 1 Jul, 8 Jul, 15 Jul, 22 Jul, 29 Jul, 5 Aug, 12 Aug, 19 Aug, 26 Aug, 2 Sep, 9 Sep, 16 Sep, 23 Sep, 30 Sep, 7 Oct, 14 Oct, 21 Oct, 28 Oct, 4 Nov, 11 Nov, 18 Nov, 25 Nov
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.
Vouchers
Accepted

Responsible tourism

Responsible tourism: Cyclades sailing & walking holiday in Greece

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

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.

Reviews of Cyclades sailing & walking holiday in Greece

You can trust Responsible Travel reviews because, unlike many other schemes, reviews can ONLY be written by people who we have verified have been on the holidays.

I am reborn! Simply the best holiday I have ever been on
Some great stories to tell the grandchildren. Would recommend to a friend
Very enjoyable
It was OK
A bit disappointing really

Reviewed on 27 Oct 2015 by

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


The whole experience, the islands were not crowded and beautiful. The sailing was great fun, I had never been sailing before, and both Annie and Sorteris knew their stuff. You were asked to help if you wanted to as well.

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


Travel light, and leave the hair dryer at home, you only need basic gear, and sunblock

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


Yes, ate at local taverna's and restaurants, and always tried to reduce the impact where we docked

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


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.

Reviewed on 06 Oct 2015 by

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


The late afternoon walks with Annie through the small villages, and especially to the monastery on the cliff, were a part of Greece many people won't see and created lasting memories for us. Annie was a wonderful guide, taking us on little-
traveled paths and educating us along the way with interesting information not found in guidebooks. Sotiris was an excellent skipper, taking us on exciting sailing journeys to these out of the way islands. It was all we had hoped for and
more in a sailing/walking holiday.

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


Pay attention to the request to pack lightly and in easy to stow bags. Take a light raincoat for spray under sail. Bring a sturdy pair of hiking shoes and if you have them, collapsible trekking poles for the uneven ground and ups/downs.
Bring your appetite, and don't be afraid to try the goat in the oven. "Cash only" on the small islands so bring enough for your meals and any purchases. (although ATM's are on every island).

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


Yes, we supported the local businesses by patronizing the small tavernas and shops along the way outside of the big resort destinations. Our sailing journeys kept fuel usage to a bare minimum, using mother nature's energy to deliver us
to the islands. We practiced proper recycling methods and reduced our waste by using reusable shopping bags.

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


It was an exciting adventure and one that we were invested in by our own efforts, thereby increasing our enjoyment of it.
Being actively engaged in the entire week sharpened our focus more so than a passive vacation. Annie and Sotiris were generous with their knowledge of all things local. We would rate our vacation as Excellent.

Reviewed on 21 Jul 2015 by

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


This question is difficult to answer as there are so many brilliant memories. However, the two events that stand out are the visit to Kimoulous and the dinner in the fish restaurant on the beach and the visit to Iraclia, the beaturiful bay, walking up in the mountains over the cliffs and the visit to the little Taverna in the village.

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


Be clear that it is a combined sailing-walking trip and hence to be prepared for living and sailing on a boat as a team. Travel sickness pills may be helpful for those that feel sea sick as even in summer the winds can be strong.

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


Yes, I was reminded again to preserve water, reuse and reduce waste. Eating in the local tavernas was one of the best and most memorable experiences, eating the local produce and helping the people in the villages especially during this financial crises.

Also thanks for the many great conversations with Annie and Sotiris who helped us so much more to understand the greek society and living in a more conscious and environmentally and socially sustainable way.

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


Excellent, thanks so much. We really enjoyed the trip, the company, the places we visited and the people we met. We will spread the word....

Reviewed on 28 Apr 2013 by

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


This is difficult to pin down. Was it seeing the dolphins (twice) or the spontaneous Greek dancing in a cafe on Amorgos?
Or perhaps the weather or the company of our hosts and the other guests.

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


Go with the flow - Soiris and Annie know ALL the best places!

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


Definitely, all the places we ate in and bought food, water or gifts from were owned by the people who lived on each island and whilst on the boat we participated (minimally I admit) in gathering information on the pods of dolphins we saw.

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


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

Reviewed on 31 Oct 2012 by

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


The special quality of the experience made this a memorable holiday. Although the Cyclades are popular islands for holiday makers we felt that we were privileged to have a really personal experience on some of the smaller islands. The random nature of the voyage and experiences of small harbours and off the beaten track hill villages took us back to an earlier age- before mass tourism.

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


Pack light! We overpacked with warm weather clothes!
Learn about the long history of the entire Mediterranean Sea.
Buy local and enjoy the delicious local foods.

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


The operator were careful to spread our custom around especially to the lesser known and more remote places in need of the extra income. This added to the quality and variety of what we ate!
The journey itself was of very low environmental impact and the team clearly had done a wide range of environmentally sound and sustaining work especially in relation to under-water issues.

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


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.

Reviewed on 21 Aug 2012 by

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


It is hard to pick one thing... I have a long list... so here are the Top 2! 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! Another day we stopped for a drink at a taverna in the hills of Amorgos. We sat outside in the narrow street. At first there were just a few of us, then some musicians came along and started to play. More chairs were brought out, more and more people came. Soon the line of chairs was all along the street. It was such a lovely gathering, like being with friends who suddenly decided to have a party.

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


To travel very light as there is limited storage space and to take covered walking shoes with good soles as some of the paths are rugged.

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


Yes, the operator is helping to support communities as they took us to some remote places – one island had only about 100 inhabitants and some were only accessible by boat or by infrequent ferries. They took us to local tavernas and cafés and suggested somewhere to stay for our second week, so we were felt that we were supporting small businesses. I think the environmental impact was limited as we were sailing most of the time and were careful about recycling and using water economically. The operator was also monitoring wildlife and looking for any changes in the marine environment.

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


It is like being on holiday with friends who share their favourite places with you and introduce you to their friends. It was lovely not to feel like a tourist and see places as they really are. A rare and very special holiday!

Reviewed on 26 Oct 2012 by

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


Memorable moments for me included swimming in the sea, eating the delicious home- cooked food on Amorgos, and the beautiful beaches on Koufonissi.

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


Pack light!

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


We went at low season, as the tavernas were starting to close and people on the
islands were returning to Athens. Because our skipper and walking guide had
friends on every island people were really happy to open up especially for us.

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


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.

Reviewed on 15 Oct 2012 by

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


The day we spent walking on Amorgos to the Monastery was fantastic. The scenery throughout the walk was superb.
Each evening we ate at a local taverna which was recommended by Annie and Sortiras, which meant at each island there was a
change in the food,

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


The walks are moderate and I would advise closed shoes as the paths can be rough with thorny plants. They advise to pack light and you do need to. Space on the boat is limited and other than walking clothes and a change for the evening you don,t need much more. There is a " bare foot" policy on the boat so a pair of flip flops is useful for slipping on when getting off the boat. You do need to be reasonably fit, as I would describe the walks as moderate and you have to get on and off the boat up gangplanks and over the side.
Remember that it is a yacht so if there is no wind you cannot sail so need to be flexible, we walked a full day and sailed a full day
rather than half and half.

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


Yes, we ate at local restaurants/ tavernas which served locally sourced food and were encouraged to buy goods as required in each place.

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


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.

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