Walking holiday in Syros



Highlights of this walking adventure holiday in syros island, cyclades

Walk on deserted ancient paths and trails, enjoy stunning mountain views and dramatic coastal scenery… come across ravishing flora and fauna… reach remote solitary beaches with crystal clear waters…

Key Information

Tour Duration: 7 days
Group Size: Small groups or private
Season: March – November
Airfare Included: No
Tour Customizable: Yes
Low season Per Person Price: 7-day package: 682 Euro (check our offers)
High season Per Person Price: 7-day package: 737 Euro (check our offers)

Picture this!

This week-long walking trail holiday will offer you the opportunity to explore the Mediterranean’s best kept secret: the Cycladic island of Syros. Based in the picturesque, historical coastal town of Ermoupolis, an Unesco World Heritage site, you will walk on deserted ancient paths and trails, enjoy stunning mountain views and dramatic coastal scenery… come across ravishing wild herbs and flowers… encounter endemic wildlife… reach remote solitary beaches and coves with crystal clear waters.

Explore the historical town of Ermoupolis, an Unesco World Heritage site.

You will learn how the island’s history has been shaped by exploring the dramatic ruins of Kastri, the neo-classical town of Ermoupolis, the medieval village of Ano Syros to name a few. You will also be given unique insights into the unique fauna and flora of the Cyclades as well as experience the local culture and way of life.

You’ll have the opportunity not only to get introduced by a local to a side of the Aegean that few people know about but also to participate in our efforts to sustain this natural and cultural environment.


Most hikes will take place at the northern part of island, called Apano Meria. It is a mountainous area with deserted ancient paths that lead through astonishing landscapes with abandoned terraces, ruined windmills, caves, bridges, steep rocky cliffs, springs and small gorges to the virgin beaches of the island… It is a NATURA 2000 protected area due to its flora and fauna which is rich in common and indigenous species.

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.

7-day recommended itinerary

Day 1: Orientation around Ermoupolis & Welcome supper
Arrival at the island of Syros and transfer to our traditional, family-run guesthouse at the coastal town of Ermoupolis. Orientation and introduction on the history and culture of the island of Syros. Ermoupolis is full of Venetian and neoclassical buildings which make it one of the most beautiful towns in the country to walk around. Welcome supper at one our favourite local taverns where you can taste the island’s acclaimed gastronomy.
Day 2: Coastal trail to the Akropolis of Kastri
Today we’ll make our way from the outskirts of the town of Ermoupolis onto a beautiful coastal trail towards the akropolis of Kastri, very famous because of its findings from the early-Cycladic civilisation (3200-2000 B.C.) During our walk you’ll enjoy magnificent panoramic views of the wild north-east coast of Syros and the surrounding islands and go through the traditional settlements of Platy Vouni and Richopo. The smell of herbs will accompany us and depending on the season you’ll be able to gather thyme, oregano, lavender, sage to name a few. Around April and May wild flowers including rare species and orchids are abound.

We’ll stop for a swim, snorkle and lunch at one of the most isolated beaches of the island, Glysoura. We will then walk towards the ancient settlement of Katri where we’ll have a break to admire its magical atmosphere. We’ll end our day’s walk at the village of Chalandriani and its local tavern with a drink and a meze.

Walking time: 3,5 hours hours. Actual walking with lunch and stops: 6 hours. Grade: moderate.

Day 3: Walk to Cape Dhiapori & the most remote beaches
Today we’ll take you to a very lonely part of the island of Syros, it’s northern tip, Cape Dhiapori, and the most remote beaches of the island, Gria Spilia and Grammata. We’ll start from the valley of Kambos and follow the beautiful trail to Dhiapori. You’re likely to spot on the way birds such as Cory’s shearwater, Eleonora’s falcon, Bonelli’s eagle, Audouin’s gull, the European shag, to name a few exciting sightings you could make during spring and autumn migration.

After a short break at the cape to admire the stunning rock formations and deep blue of the Aegean, we will continue towards Grammata beach where you’ll enjoy a swim and snorkle at its crystal clear waters. After a short walk we’ll stop at the shaded beach of Gria Spilia for lunch and a rest before returning. In the evening we’ll explore the little village of St. Michelle and have supper enjoying the most impressive sunset

Walking time: 3 hours. Actual walking time: 5 hours. Grade: moderate.

Day 4: Historical & cultural walk
Today we’ll start our walking adventure from the elegant marble square of Ermoupolis. We’ll walk through the narrow alleys of this “mysterious” town towards the quarter of Vaporia, an architectural splendor with beautiful neoclassical mansions, cobbled streets and arches. We’ll continue to the top of the hill Dili reaching the famous Orthodox church of Anastasi, standing opposite to the Catholica church of St. George, a symbol of the harmonic co-existence of the two religions, where you can enjoy mind-blowing views of the harbour and Ano Syros. That’s where we’ll stop for a rest and a pic-nic.

Late in the afternoon you will enjoy one of the most pleasant strolls towards the medieval town of Ano Syros, built by the Venetians in the 13th century, and the surrounding rural area. Innumerable steps between narrow marble streets and old stoney, white-washed houses with coloured doors lead to the top of the town. The Catholic basilica of San Giorgio dominates. You will enjoy a panoramic view of the Ermoupolis and the neighbouring islands of Tinos, Delos, Mykonos, Paros, Andros and Naxos. We will watch the colourful sunset and then enjoy local delicacies and traditional island music at one of the island’s oldest taverns.

Walking time: 3 hours. Actual walking time: 5 hours. Grade: moderate.

Day 5: Rest day
Opportunity to rest or explore the island’s numerous beaches, the neo-classical town of Ermoupolis or the medieval town of Ano Syros. The options are endless and we’ll be happy to offer you advice.
Day 6: Ancient trail with panoramic views
Today we’ll make our way towards the traditional settlement of Papouri and from there we’ll take the ancient trail towards the beach of Varvaroussa, that is ranked amongst the islands’ nicest beaches. You can have lunch and swim at the bays’ secluded, turquoise waters. Our guide will be happy to take you snorkeling around the rocks of a little island inside the bay of Varvaroussa and introduce you to the unique underwater biodiversity of the East Med.

From Varvaroússa we will then enjoy a walk along the coast to the beach of Delfíni and then further to the bay and settlement of Kíni. The trails are very beautiful, the panoramic views are marvellous… We will end the day with supper at one of our favourite local taverns.

Walking time: 2,5 hours. Actual walking time: 5 hours. Grade: Moderate.

Day 7: A walk through a world long gone...
Today we’ll explore the south part of the island and the village of Chroussa, a village that is characterised by a forestry element in contrast to the rest of the island. It is here where the aristocracy, mainly ship owners, used to build their luxurious mansions. We’ll walk through the old paved alleys of the deserted village and we’ll explore the old derelict mansions, a walk through a world long gone…

We’ll have a pic-nic at the top of the hill under the shade of pine trees while admiring the magnificent views of the endless deep blue of the Aegean sea and the islands of Naxos and Paros. We will then descend towards the coast. You’ll have the opportunity at the end of our exploration walk to enjoy a swim and snorkle at one of the beaches around the bay of Vari.

Walking time: 2,5 hours. Actual walking time: 5 hours. Grade: moderate.


We have reserved for you a lovely authentic family-run guesthouse. It was built in the 18th century and was originally hosting the French embassy. It has been beautifully restored and converted to provide 3 really spacious suites with great views and 3 double rooms in the centre of Ermoupolis. The owners are very hospitable and helpful and are known to provide the most delicious breakfasts.


We organise these walking trail holidays all year round apart from mid July to the end of August when it’s too hot.

Learn all about the island’s history, culture, archaeology, wildlife, herbs and their uses.

green_bullet  March: blossom is out.
green_bullet  April to mid June: for wild flowers, sunshine and moderate temperatures. The Easter period is recommended as it’s one of the most important celebrations in Greece and you’ll have the chance to experience traditional feasts and gatherings.
green_bullet  September to– end of November: for warm seas, gentle weather and autumn flowers. Grapes and olive harvests are in September-November.

Syros is the capital of the Cyclades, in a very central location and with good connections to all Cycladic islands, if you wish to continue your holiday.

The combination of natural beauty and culture but also the hospitality of her residents will make this holiday unforgettable for you.

green_bullet Check our fees!

green_bullet How we walk towards nofootprint…

green_bullet Check photos from this eco-friendly walking adventure in Syros island…

green_bullet Check Matt Barett’s Guide to the Greek islands…