Cyclades walking holiday, Greece

Walk for hours without spotting a single sole and discover the rare plants, coastal birds and neoclassical architecture of Syros, one of the Greek islands hidden gems.
Syros Island UNESCO site of Ermoupolis Katri acropolis Birdwatching Snorkelling Medieval town of Ano Syros Varvaroussa Beach Chroussa village Eating in local tavernas Scenic inland and coastal walks
£647To£720 excluding flights
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7 Days
Small group
More info
Fees are per person for two people sharing a double room.
Single room supplements available.
Fee includes guided walks, 4-star guesthouse, breakfast, VAT, transfers, presentations on Aegean flora & fauna.
Combine with walks at Tinos & Andros.
116 Eur off on 8 April, 22 April or 13 May
Make enquiry

Description of Cyclades walking holiday, Greece

This week-long walking trail holiday will offer you the opportunity to explore the Mediterranean’s best kept secret: the Cycladic island of Syros.

Every day will bring walks along deserted ancient paths and trails, with plenty of opportunities to enjoy stunning mountain views across the Cyclades Islands and their dramatic coastal scenery. As well as remote, solitary beaches and coves with crystal clear waters. Syros has both cultural and natural highlights, with ancient archaeological sites at Kastri, the Venetian castle reservation of Ano Syros as well as the elegant neo-classical main town of Ermoupolis. The island is rich in varied terrain from Apano Meria, a mountainous, rugged area of the north, a NATURA 2000 protected area due to its prolific flora and fauna, to the forested and quiet, abandoned village of Chroussa in the south. With Aegean views to die for at every stop, remote beaches at the end of every trail, and waterside tavernas to delight at the end of each day.

You will continue to explore the “unknown” Cycladic island of Tinos with its numerous deserted ancient paths and trails, enjoy the architecture of pigeon houses, windmills and countless churches, stone walls, fountains, giant rocks with strange shapes…

You will walk through villages untouched by time with picturesque houses, arches, carved doorways, marble fountains, cobbled streets… you will reach and swim at stunning, secluded beaches with fine sand and crystal clear waters… you will taste Cycladic delicacies such as local cheeses and proscuito “Louza”, froutalia omelette…

Both in Syros & Tinos you’ll be surprised as you may not encounter any other walkers within a week. The feeling of wilderness prevails although we’re never far from civilisation.

We always aspire to be flexible with our itineraries according to our guests’ needs and interests. What we can’t be flexible with, however, is the weather, which is just too hot for walking in July and August, so we don’t offer trips during these times. We think that the best time for a Cyclades walking holiday is:

*March when the tree blossoms are blooming
*April to mid-June when the wild flowers are bursting, and temperatures are not too hot. We also recommend Easter on Syros, as it is a wonderful time to experience Greece’s culture, with traditional feasts and celebrations going on all over the island
* September until the end of November: the seas are still warm, the temperatures balmy and the grape and olive harvest take place, with more local festivities to enjoy.

Price information

£647To£720 excluding flights
Convert currency:
Fees are per person for two people sharing a double room.
Single room supplements available.
Fee includes guided walks, 4-star guesthouse, breakfast, VAT, transfers, presentations on Aegean flora & fauna.
Combine with walks at Tinos & Andros.
Make enquiry

Check dates

2023: 1 Apr, 15 Apr, 29 Apr, 13 May, 27 May, 2 Sep, 16 Sep, 30 Sep, 14 Oct, 28 Oct

Travel guides

Greece walking
There’s just something about walking in Greece that expands the sensual appetite. Maybe it’s the ocean breeze; goat bells in the mountains; perhaps th...
The Cyclades translate as ‘a circle of islands’ and the Greek gods must have had a perfect view from up there on high to see this lovely layout of isl...

Holiday information

Our top tip:
Although tours take place outside 'peak season' they still experience daytime heat and, conversely, evening chills. Pack layers for peeling off or putting on.
Trip type:
Small group and tailor made tours. Max 6 people.
Activity level:
Moderate. Daily walks taking 5 hours or more with ascents up to 500 metres.
Family-run 18th century guest house in Ermoupolis.
Local tour guides: Annie and Dimitris, and accommodation.
All breakfasts, daily picnics using local produce and evening meals at local restaurants.
Solo travellers welcome.
We cater for both vegetarians and vegans.


11 Reviews of Cyclades walking holiday, Greece

4 out of 5 stars

Reviewed on 19 May 2019 by

Great walking, great food, great guide (Annie) and great hotel in Sifnos Read full review

Reviewed on 10 May 2019 by

The most memorable parts were the wonderful people, mountains, flowers, and beautiful bodies of water in Greece. Read full review

Reviewed on 13 May 2018 by

Hard to pick one the most memorable moment, maybe climbing up to monastery on highest point on Sifnos. Fantastic views from the B&B whatever the time of day. Both islands were really interesting. Read full review

Reviewed on 01 Jun 2017 by

The most memorable was climbing the peak to San Simeon on Sifnos. Read full review

Reviewed on 11 May 2016 by

This holiday fulfilled my expectations in providing amazing walks off the beaten track and the opportunity to see rural places not visited by most tourists. Read full review

Reviewed on 24 May 2015 by

Our guide was able to speak to everyone and we were welcomed and given fruit, honey, drinks, desserts, and wine. Our a accommodation owner gave us a tour of his orange farm and marmalade. The island, villages, and ocean were beautiful. Read full review

Reviewed on 25 Apr 2015 by

The most memorable parts of the holiday were walking in Syros & seeing the beautiful scenery & wealth of wild herbs & flowers. Also Annie was a great guide and very attentive to us, and helped the group in many ways. Read full review

Reviewed on 14 Apr 2015 by

The scenery, food, culture and company were all fantastic. A fantastic introduction to Greece. I will be going back to explore some of the other 1000 islands! Read full review

Reviewed on 04 May 2015 by

Excellent. Walking along tracks and hidden footpaths over rugged hills filled with wild flowers and fragrant herbs, down to secluded beaches. Read full review

Reviewed on 08 May 2014 by

Very enjoyable, it’s the first hiking holiday we have done...wonderful fresh air, beautiful scenery, small plants and scents, and nobody around. We felt very peaceful, and relaxed. Read full review

Reviewed on 23 Oct 2013 by

Very relaxing and enjoyable. People were very friendly and nice. Great food. Read full review

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.


This walking trail holiday in the island of Syros, has a primary eco-focus. We are dedicated to encouraging low-impact activity holidays, such as walking, and minimising our negative impact on the environment and people. This is mainly done by respecting the natural environment of the places we visit and by concentrating on an alternative way of travelling, mostly out of the heavy burdened touristic summer season.

We try to support the No Footprint idea by exploring in small group numbers and as much as possible getting around on foot or by public transport. Our walking holidays after all, leave nothing but footprints behind! We walk on designated paths and make sure no litter is left behind, while we also gather up any that we see on our way. We often arrange clean ups of paths and beaches during the week, or tree planting initiatives in these dry and arid Greek islands. We report on paths that are falling out of use and help to clear or shape them back.

Most of our paths are part of larger protected areas or National parks and Natural reserves, such as the vast Natura 2000 network. This way, we encourage our guests to behave in an environmentally responsible manner. We inform our guests about the unique flora and endemic and common species they will encounter while walking or swimming around Syros island. We find it to be important to encourage and develop a passion for wildlife and wild places among our customers. We give guidelines on where to look for them, how to observe them or even capture a unique picture showing to the rest of the world their magic. Of course, it is important to emphasize that all wildlife sightings are a bonus; none are guaranteed! We practice Responsible Wildlife Viewing principles by not disturbing or threatening the behaviour of any wild animal by no means. We ask our guests to never remove a specimen – whether plant, seed or animal – from its natural environment. Guests leave aware of the environmental dangers faced and what they can do themselves to minimise them.

We encourage our guests and the owners of the accommodations we use to be aware of the threats to the environment (i.e. water waste, plastic bags and bottles) and suggest ways in which they can minimise their negative footprint. We explain to our guests the need for water conservation in the Greek islands and advise them on how to minimise their water waste. We encourage our guests to bring refillable water bottles and/or recycle them in designated areas. All communication is done electronically where possible, saving on paper


We have the greatest respect for the local people and their customs and are anxious to share our knowledge of Cycladic island lifestyle with our guests. Your guides are all local, sharing with you their ideas and love for their land. In order to limit the social impact of tourism all are guests are introduced to the local customs, religion, politics and history during our walks. We take our clients to local festivals, artists' workshops, and other local celebrations trying to get them to experience the local way of life. We encourage our guests to mix and interact with the local people which are particularly friendly and hospitable.

Through our walking trail holidays in Greece we support small businesses by supporting locally owned shops, guesthouses, mini-markets, bakeries and taverns. As our holidays take place in spring, early summer and autumn, we bring customers and income to establishments which would otherwise only have visitors in the high touristic summer months. In many villages, we visit local craftswomen who make their own handmade traditional products and by selling them, support their families.

All the products used in our picnics are bought locally, by small family-owned shops, supporting a low carbon diet and respecting the seasonal produces, thus supporting the local agricultural community. Evening meals are taken in typical Greek restaurants serving local, Greek and Mediterranean dishes, usually with products from their own personal gardens.

We opt for local, family owned guesthouses, staffed by locals. These accommodations have been restored by local workers and retained their unique local character whilst providing all necessary comforts. The guesthouses recently installed solar panels which provide hot water for all rooms all year round.

In general, with all walking holidays in Greece, we’re trying through our activities to encourage travellers to approach places they visit with greater understanding and respect.

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