Cyclades Sailing and Walking holiday



HIGHLIGHTS OF our Cyclades sailing and walking holiday

Discover the magic of sailing from island to island!

Experience the unique nature and landscapes of these small, non-touristy Greek islands by walking their ancient paths…

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: 774 Euro (check our offers)
High season Per Person Price: 7-day package: 860 Euro (check our offers)

Picture this!

Join our Cyclades sailing and walking holiday, sail with us during the day and in the evening walk at the tips of mountains that offer breathtaking views to the Aegean sea, traditional villages, byzantine and ancient settlements… and reach virgin beaches where you can rest and have a refreshing swim.

Here is a sample of what you’ll experience while sailing & walking with us for a week around the Greek islands…

Day 1: Briefing and welcome supper at the old town of Naxos
Meeting at the island of Naxos in the evening. Briefing, arrangement of provisions and supper at one of our favourite taverns in the old town. Check the island’s beaches, enjoy a short walk to the temple of Apollo and watch the sunset or walk around the picturesque alleys of the old town leading up to the castle.
Day 2: Walk to Zas, the Cyclades' highest peak & sail to Naxos
We’ll start the day with a visit to one of the island’s most picturesque villages, Filoti. Within an easy 2 hour walk you will conquer the Cyclades’ highest peak, Zas. The view from the top to the Aegean Sea and the islands of the West and Small Cyclades is really mind blowing. We’ll rest and have a picnic admiring the view. We’ll then descend towards Agia Marina and go back to the boat. Late in the afternoon we’ll sail towards the remote bay of Kalando in the South of Naxos. We’ll enjoy a barbecue on the beach.
Day 3: Sail to Iraklia & hike to cave with stalactites
After a morning swim we’ll sail to the little fishing port of Iraklia. You have the day to relax and swim and check the island. Early in the evening we’ll walk from the hora, Panayia, to the cave of St. John. It’s an hour hike to the largest cave of the Cyclades, famous for its formations of stalactites. On our way back to the village we’ll enjoy the sunset from the top of the hill. You’ll have the chance to enjoy home made food during supper at the local bakery/tavern at Panayia.
Day 4: Sail towards Amorgos & circular walk around traditional villages
Sail towards the mountainous island of Amorgos. We’ll stop on the way for lunch and a swim at the crystal clear blue water of the deserted island of Antikeri. We’ll continue our sail towards the fishing port of Aegiali where we’ll spend the night. In the evening, we’ll walk the circular ancient path, covered with various endemic and local herbs and flowers, around the villages of Tholaria, Stroumbos and Langada where we’ll enjoy traditional island music and delicious dishes at one of its taverns.
Day 5: Hike to Stavros to admire the most impressive view
Today the day will be dedicated to hiking and discovering the island’s northeast area which is characterised as a Natura 2000 area due to its unique flora and nature. We’ll start our hike from the beautiful village of Langada. We’ll follow the narrow path towards the impressive church of St. Theologos, where we’ll rest and have a snack under the shade of one of the church’s outhouses. We’ll then take the trail towards the small church of Stavros, on the highest hill of Amorgos, where we’ll admire the impressive view of rock formations and deep blue sea underneath. Relax and enjoy one of Aegiali’s beautiful beaches for the rest of the day.
Day 6: Sail & walk on remote island of Kato Koufonisi
We’ll set sails towards the islands of Koufonisia, known for their crystal clear turquoise waters and beautiful beaches. They also belong to the Natura 2000 network. We’ll spend the night on the anchor at one of the beautiful bays of Kato Koufonisi. In the evening we’ll enjoy a walk around the island and have supper at the tavern of the only family that lives in the island. They have their own animals and produce all their vegetables and fruits themselves. We don’t have words to describe the quality of food you’ll taste!
Day 7: Sail to Paros & walk the Byzantine path
Last day sailing towards the island of Paros and the fishing port of Piso Livadi. Early in the evening we’ll go to the one of the oldest villages of Paros, Lefkes, and walk for an hour towards the picturesque village of Prodromos. We’ll have supper at the local ‘cafeneio’ and enjoy Greek hospitality and home-made food. If we’re lucky locals we’ll entertain us with live music!


The walks during our Cyclades sailing and walking holiday are graded as easy to moderate. Being predominately limestone some parts of our paths can be quite rough and stoney so a good pair of walking shoes is required.

Flexible itineraries are available based on the needs of our guests. We can organise a more challenging or a more relaxed-pace itinerary offering you more time to relax and enjoy the sea and sun of the Cyclades.


We organise our Cyclades sailing and walking holiday all year round apart from mid July to the end of August when it’s too hot.

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.

We have reserved for you a lovely authentic family-run guesthouse at a very central location.  The owners are very hospitable and helpful and are known to provide the most delicious breakfasts. We’ll send you full details.

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

green_bullet Check our fees!

green_bullet How we walk towards nofootprint…

green_bullet Check photos from this eco-friendly sailing & walking adventure…

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