Walking holiday in the West Cyclades, Greece

A ten day, small group walking holiday taking in glorious western islands such as Milos, Sifnos and Serifos. Cyclades at their most secluded.
Serifos Sifnos Ancient site of Agios Andreas Milos
£895To£1029 excluding flights
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10 Days
Small group
More info
Fees are per person for two people sharing a double room.
7, 10, 14 day options including Santorini & single supplements are available.
Fee includes guided walks, accommodation, ferries, transfers, VAT, info on local history, culture, flora & fauna.
Make enquiry

Description of Walking holiday in the West Cyclades, Greece

This ten day Cyclades holiday, walking around the western islands of Milos, Sifnos and Serfios is a journey around some of Greeceís most magnificent island walking trails. These ancient tracks and paths, used for farming or trading, take you through small rural villages with traditionally Greek white stone houses, Byzantine chapels, and architectural remnants from Venetian times. As well as the obligatory beach perfection at the end of road.

Each island has its own unique quality. For example, the island of Milos is volcanic and so, as well as its forty odd beaches, there are caves, rock formations and other fascinating geological wonders to explore. And, in addition, plenty of wild flowers, olive groves, cypress forests and fauna ranging from seals to a symphony of sea birds. Each of these islands has been awarded protected status by ďNatura 2000Ē because of rare habitats for endemics like the Milos wall lizard or Milos viper. And Sifnos island, as well as boasting 100km of trails, is also renowned for its fine cuisine, as exemplified by the islandís gastronomic hero, Nikos Tselemendes, a renowned early 20th century chef from Sifnos. A cookery book named after him, Tselementes, is packed with traditional Greek recipes and his legacy lives on in Sifnosí restaurants.

On this holiday you will be accompanied by local guides who are not only experts in local cultural heritage but also all the natural highlights too, which they will cover in presentations and chats during the trip.

While our schedule is very flexible according to the groupís interests and abilities, please do read our sample itinerary to get an idea of the sorts of terrains and trails we will cover during this Cyclades walking holiday.


Day 1:Our walking holiday begins on the island of Serifos, where you check in to a family-owned guesthouse. From here we hike to one of the islandís most stunning beaches, Psili Ammos, a good way for you to truly immerse yourself into idyllic island life. We toast the start to this holiday in the Chora, where we will dine at one of the top local tavernas.
Day 2:Todayís hike starts in the village of Kallitsos set into a fertile, lush vale of oak trees and Cycladic wild flowers, from where a cobbled trail takes us up towards the remains of ancient villages, Xero and Profitis Ilias. En route you will spot traditional pigeon houses, where local people bred the birds for meat and fertiliser. Not too tough a climb, the reward is in the views out across the Aegean and the Cyclades, in order to admire panoramic views of the island and the deep blue sea. From here, we progress along an old rural path to another deserted village of Triandafillos, where you can visit Skopiani church, and continue to stroll onwards through orchards and oak forest.
Day 3:Our hike starts in the now deserted village of Pyrgos leading to the ancient rural settlement of Galani. Set beautifully into the surrounding hills, we can enjoy superb views over one of the islandís bays at Skyamia, which beckons us for a swim and picnic, plus a well deserved rest under tamarisk trees, typically found on the saline soils of these islands. Hiking back to the harbour, we pass a 10th century Byzantine chapel, before taking a ferry to our next island stopover, Sifnos. After checking into our locally owned accommodation, we have dinner at the islandís main hub of Apollonia.
Day 4:Our walk into the interior of Sifnos leads us past charming architectural heritage such as the Profitis Ilias monastery and the beautiful chapels of St Marina or Panayia Toso Nero. These utterly tranquil walks take you not only back in time but also to sublime beaches such as the one at Vlasi. So always pack your swim gear in your backpack, with plenty of time for paddling and picnicking. Walking on Sifnos is like entering a natural perfumery, with wild herbs such as lavender or oregano filling the air at many spots along the way. As do many of the islandís wild flowers, particularly in spring. There will be plenty of herbs on offer at the local taverna in Kamares port tonight too, where the traditional Greek food is famously good.
Day 5:Hiking a stunning walking trail from Apollonia to Kastro, we wind our way through Greek rural paradise filled with olives, grapes and honey. Similar to Serifos, you will also pass some of the old wooden pigeon houses scattered around the place dotted in between beautiful villages, such as Kato Petali and Kastro, the latter dating back to prehistoric times. Todayís beach treat is nearby, leading on to a coastal walk where sea birds such as shags and various gulls thrive. After visiting Panayia Poulati church, we head back to Artemonas village, far from rural it boasts Venetian and neoclassical architecture in its various mansions that still stand proud today. We finish our walk passing through the village of Ano Petali and, last stop of the day, at Apollonia, the islandís capital.
Day 6:Today is free of set plans, giving you a chance to have a rest, find a beach to enjoy, or go and explore other sites on the island. Our expert guide is always on hand to give tips and recommendations.
Day 7:Todayís walk takes us to one of those magical spots on the island which is only accessible using boot or boat power. Fikiada Bay. We opt for the former, of course, heading out from Vathy Bay, strolling through the islandís protected Natura 2000 area, and arriving at Fikiada in time for a picnic lunch and a swim, in turquoise paradise. This is also a top spot for snorkelling. Because not only is the island celebrated for its biodiverse wonders at the Natura 2000 site, its underwater ecology is worthy of close examination too. A final stroll takes us to one more splendid bay, at Platy Yalos where we dine at a top fish taverna.
Day 8:Today we will hike to the islandís most stunning archaeological site, the unearthed Mycenaean town of Agios Andreas, perched on a hill with superb views over the island and out to the Aegean. From here we walk on to our picnic spot for the day, beside Agios Nikolas TíAerina monastery. And then, as is now tradition, to the beach, this time at Vathy, another great sunset spot. Followed by dinner at a local taverna, with no shortage of local live music.
Day 9:This morning we take the ferry to the island of Milos. Hiking here is exquisite, taking on its voluptuous volcanic terrain, sauntering through picture postcard perfect natural harbours, and embarking on the challenge of Fylakopi canyon where we start this hike - an impressive send off with Minoan archaeological remains. Following the coast as far as Papafranga, where a canyonís river, every shade of blue on the palette, leads dramatically out through a sea arch into the sea at Pachaina. Itís one of those dreamy places you just want to dive into. More coastal panoramas await on our next walk to see the caves, arches and rocks at Ag. Konstantinos harbour, with the islandís volcanic influences being also seen at Sarakiniko beach, where rocks have been eroded into dramatic shapes that give it another worldly feel. We finish this wonderful day walking on Milos at the small port of Mandrakia for aperitifs, moving onto Plaka village for dinner at a restaurant with one of the islandís greatest views over the bay.
Day 10:Starting in Adamas, we hike through tranquil farmland to get a sense of the Cycladic ecosystems, where wild herbs such as sage thrive, and arid plants like mastic or genista add blasts of colour to the island environs. We walk to a village called Trypiti which means Ďfull of holesí because the volcanic nature of the landscape means that the ground opens up easily, and as such, ancient tombs were built into the earth. The village was built on top of these, and you can visit the ancient catacombs as well as the nearby site of old Milos town, now an archaeological highlight of the island. Particularly because it was where the statue ĎAphrodite of Milosí was unearthed in the early 19th century. Our final day comes to a close walking through the remains of this great site en route to the coast, where we celebrate our island odyssey with a final group dinner.

Price information

£895To£1029 excluding flights
Convert currency:
Fees are per person for two people sharing a double room.
7, 10, 14 day options including Santorini & single supplements are available.
Fee includes guided walks, accommodation, ferries, transfers, VAT, info on local history, culture, flora & fauna.
Make enquiry

Check dates

2023: 30 Sep, 7 Oct, 14 Oct, 21 Oct, 28 Oct

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9 Reviews of Walking holiday in the West Cyclades, Greece

4.5 out of 5 stars

Reviewed on 23 Sep 2022 by

Wonderful Annie our guide was excellent and the hiking exceeded my expectations. Great food was a bonus. Read full review

Reviewed on 21 Sep 2022 by

Excellent. The guide was wonderful, the hikes varied and interesting, the food delicious and the accommodation very comfortable. Read full review

Reviewed on 10 Oct 2021 by

It was an excellent choice for us, even as we had to compromise on the amount and distance of walks/hikes we could accomplish. all of the staff at the operator were superb, and most of the local hotels treated us like family. Read full review

Reviewed on 05 Nov 2018 by

The most memorable part was sharing the delicious meals with new friends after a days walking... It was wonderful thanks to Anna's local knowledge of geology, places to stay & eat. Read full review

Reviewed on 02 Nov 2018 by

The holiday was excellent It was wonderful to spend our days exploring the varied landscape, villages and beaches of the small lesser known islands of Milos and Sifnos. Read full review

Reviewed on 02 May 2017 by

The highlight was reaching some amazing views by walking and then having a delicious dinner at a small Taverna serving local specialities. This was a lovely holiday and our guide Annie was very well organised and friendly whilst being flexible and relaxed which made the trip very enjoyable. Read full review

Reviewed on 24 Apr 2017 by

Beautiful views. Very relaxed. Times were respected. Read full review

Reviewed on 24 Jun 2014 by

Excellent...we stayed at a family run guesthouse, ate at local taverns, tried local products, used public transport and walked to get to places. We cleaned up a beach after having a picnic. Our guide in general provided useful information about the local flora and fauna, the culture, economy and environmental issues Read full review

Reviewed on 20 Apr 2014 by

Very interesting and enjoyable. We're very pleased with the experience. The hiking was great exercise. However, I think the most memorable part will be the good company we had in Annie Antonatou, our guide and host. 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 Serifos & Milos, 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 the waters of the Aegean. We find it to be important to encourage and develop a passion for wildlife and wild places amongst 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 Ė whether plant, seed or animal Ė 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, weíre trying through our activities to encourage travellers to approach places they visit with greater understanding and respect.

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