Cyclades sailing & walking vacation in Greece
A week-long vacation of island-hopping, hiking and all round Hellenic hedonism in the Cyclades archipelago of Greece.
Six days sailing the Cyclades Naxos Temple of Apollo Iraklia Island Cave of St. John Amorgos Island Koufonisia Islands Paros Island
Price
£788To£1045 excluding flights
More info
Price is per person based on groups of 6 guests.
Private tours avail.
Price includes skipper, walking guide, accommodation on our sailing yacht, daily walks, breakfast, snorkeling equipment.
Contact us for more info & special offers.
Private tours avail.
Price includes skipper, walking guide, accommodation on our sailing yacht, daily walks, breakfast, snorkeling equipment.
Contact us for more info & special offers.
Offers
£100 off Sept & Oct departures
Description of Cyclades sailing & walking vacation in Greece
Price information
Check dates
2026: 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
Travel guides
Our sea splashed Greece walking vacations guide has everything you need to know about island and mainland trails.
Greece’s sapphire waters are perennially dotted with the white sails of little boats.
Vacation information
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 travelers welcome. Surcharge for own cabin.
Diet:
We cater for both vegetarians and vegans.
Reviews
26 Reviews of Cyclades sailing & walking vacation in Greece
4.5 out of 5 stars
Reviewed on 18 Oct 2025 by Laurie Dunn
Fantastic - by far the highlight of our trip to Greece. Read full reviewReviewed on 18 May 2025 by Phillip Henshall
This is an active adventure vacation with solid sailing and walking. It is fun but not luxurious. Great time. Good skipper and crew/guide. Read full reviewReviewed on 25 May 2024 by Laura Coleman
This is the opposite of mass tourism; local people on their own boat, who take you to places where they feel you will eat local food in an authentic setting. Read full reviewReviewed on 30 Sep 2024 by Colin Masson
Balance of good sailing with beautiful walks/hikes in genuine Greek villages. Very experienced guides and Captain - utilizing their knowledge and expertise to provide us a wonderful experience. Read full reviewReviewed on 16 Oct 2023 by Linda Noeske
The captain, the guide, the small Cyclades islands and the dinners at the family taverns and the beaches and the hiking on unmarked trails. We are 3 women in our seventies so the captain and guide adapted and paced the sailing, swimming and hikes to our abilities. Read full reviewReviewed on 24 Sep 2023 by Will Mouger
If you want to help with the sailing take a different vacation. Although he is an excellent boat-handler, the skipper is not a good host on his boat and is often terse and very challenging.The tour (walk) guide was very nice, chatty and cheerful, in contrast to the skipper. Read full reviewReviewed on 02 Nov 2022 by Angela Cohen
The sailing was super exciting under the expertise of our skilled skipper Sotetis. And the afternoon walks with Annie so memorable and informative. Their local knowledge was invaluable and so interesting, we met some wonderful local people and ate at delicious restaurants. Read full reviewReviewed on 17 Oct 2022 by Julie Hancock
Absolutely fantastic, an amazing way of seeing and experiencing real Greece. Read full reviewReviewed on 25 Sep 2022 by Agnes Schrider
Outstanding and a terrific adventure. Because of Sotiris and Daphne , we really feel we had an authentic experience and got a sense of Greek culture and the spirit of the people. Read full reviewReviewed on 18 Sep 2022 by Laurie Rood
I really enjoyed the adventure with our fun loving experienced team... They had friends in every port and are beloved by the locals. Great value and a wonderful trip. Read full reviewReviewed on 06 Jun 2022 by Anne-Marie Mayer
Very good... my third time and it was great to be back. Read full reviewReviewed on 09 Jul 2022 by Annabel Simms
The rebetiko musicians at Aegiali on the isle of Amorgos. Read full reviewReviewed on 12 Nov 2021 by David Nimkin
It was a wonderful trip. It contrasted well with a hiking adventure we took in the Peloponnese prior to the sailing and offered a perspective on island life during a period when the tourist rush was winding down. Read full reviewReviewed on 15 Sep 2021 by Jane Hart
One of the best vacations we have ever had - Annie and Sotiris the skipper of the boat were great hosts, the sailing, walking and diving were all incredible, and the hospitality of the island people we met was wonderful. Read full reviewReviewed on 20 Sep 2019 by Caroline Pack
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 reviewReviewed on 15 Sep 2019 by Catherine Pedersen
Fantastic guides Annie & Dimitria who showed so much care, thoughtfulness & took us on fantastic walks. Read full reviewReviewed on 28 Jun 2019 by Jennifer Duschenes
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 reviewReviewed on 27 Jun 2018 by Lyndsay Gough
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 reviewReviewed on 08 Oct 2018 by Jennifer Simon
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 reviewReviewed on 24 Oct 2017 by Jane Cousins
Fantastic! Very memorable. Something I'd want to repeat. Read full reviewReviewed on 17 Sep 2017 by Angela Wingfield
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 reviewReviewed on 27 Oct 2015 by Louise jones
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 vacation. Read full reviewReviewed on 06 Oct 2015 by Joann Dupuis
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 reviewReviewed on 21 Jul 2015 by Gesche McGibbon
Excellent, thanks so much. We really enjoyed the trip, the company, the places we visited and the people we met. Read full reviewResponsible Travel
As the pioneers of responsible tourism, we've screened this (and every) vacation so that you can travel knowing we've worked to maximise the benefits of your vacation to local people and places, and minimise any negative impacts.
Planet
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 travelers 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.
People
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.
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