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Sailing and hiking


Sample itinerary


Sailing and hiking adventure holidays in Greece

Cyclades islands hiking and sailing tours

Combine a sailing & hiking adventure around the islands of the Cyclades…

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

Explore the stunning islands of the Cyclades aboard our fully crewed sailing yachts. There is nothing better after a day of great sailing than to relax in the spacious cockpit and enjoy a sun-downer with your fellow sailors, before exploring each new location the islands or the sea have to offer.

Yacht: TAHITA Sun Kiss 45

On our sailing yacht "Tahita" (Jeanneau Sun Kiss 45) we can accommodate up to 6 guests in 3 double cabins. Your crew: Skipper and Divemaster will occupy a separate crew cabin.

The Sun Kiss 45 is one of the most exceptional and elegant classical models created by Jeanneau, known and recognised for its strength and sailing capabilities, for sailing as well as cruising the world over.

Tahita can accommodate 8 people in its 3 double cabins and skipper cabin. There are 2 toilets/showers and a stern shower on the diving platform. In order to guarantee the maximum space and comfort for our guests, we take up to 6 people each time, while keeping the cost at a minimum.


Read more about the yacht and her crew...

Below is a sample of what you will experience while sailing & hiking with us for a week… please note itineraries vary week by week, with embarkation / disembarkation also from Syros, Paros, Naxos, Milos - all of which are well connected by ferry from Athens.

Sailing in Greece

Sample itinerary of a typical cruise

Charters run from Saturday (check in: 17:00) to Saturday (check out: 09:00)
Hiking and trekking cruises are offered from April - June and from September - October (but not July and August as it is too hot for walking)
Eco-wildlife cruises and scuba diving cruises are also offered April - October..

Temple of Apollo

Day 1: Welcome to Naxos & exploration of the Old Town

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. During the day you can explore the island's beaches, enjoy a short walk to the temple of Apollo to watch the sunset or walk around the picturesque alleys of the Old Town leading up to the Venetian Castle.

Cyclades islands

Day 2: Walk to the highest peak of the Cyclades to admire the view

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 panoramic view. We'll then descend towards Agia Marina church and go back to the boat. Late in the afternoon we'll sail towards the remote bay of Kalando, south of Naxos. Time for a barbecue on the beach.


Day 3: Sail to the Small Cyclades & walk to cave with stalactites

After a morning swim we'll sail to the little fishing port of Iraklia. Relax, 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 you'll enjoy the sunset from the top of the hill. You'll have the chance to taste home-made dishes during supper at the local bakery/tavern at the hora.


Day 4: Sail to Amorgos & circular hike around traditional villages

Sail towards the mountainous island of Amorgos. We'll stop on the way for lunch and swim at the crystal clear blue waters 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, you'll enjoy a short hike to the village of Tholaria where you'll enjoy traditional island music and delicious dishes at one of its taverns.


Day 5: Hike along the spine of Amorgos

Today the day we'l be dedicated to hiking and discovering the island's northeast area which is characterised as a strong>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 Stavros enjoying 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 & coastal walk at 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 you'll enjoy a walk around the island and have supper at the tavern of the only family that lives on 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 visit 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 ‘kafeneio’ and enjoy Greek hospitality and home-made food. If we're lucky locals we’ll entertain us with live music!

We’re as flexible as the weather!

The above itinerary is an example of what you will experience on our Sailing & Walking holiday around the islands of the Cyclades. We don't follow the same route every week and the itinerary may slightly change due to the weather and other factors beyond our control. Remember that we cannot go against the weather! We will do our best.

Guests' Photos

Sail and hike through the Greek islands

Hiking tours

Dolphins Small Cyclades


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Antonopoulou 158D, Volos, 38221, Greece
Tel: +30 24280 94128 | Tel: +30 24210 36676

Odyssey Sailing is registered and bonded with the Greek National Tourist Organisation (GNTO - EOT)
and is a member of the Hellenic Yacht Brokers Association (HYBA).

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