Cyclades island hopping to Santorini

Cyclades island hopping to Santorini


HIGHLIGHTS OF THIS Cyclades island hopping to Santorini WALKING HOLIDAY 

Combine a walking holiday island hopping around Naxos, the Small Cyclades & Santorini…


Tour Duration: 10 or 14 day(s)
Group Size: Small groups
Season: March – November
Airfare Included: No
Tour Customizable: Yes
Low season Per Person Price: 10-day package: 974 Euro, 14-day package: 1,364 Euro
High season Per Person Price: 10-day package: 1,052 Euro, 14-day package: 1,474 Euro


During our Cyclades island hopping to Santorini, you can combine a walking holiday starting from Naxos, continuing to the Small Cyclades and ending in Santorini.

Naxos is the largest, richest and most multifaceted island of the Cyclades with lofty mountains, fertile valleys, springs, rivers, picturesque villages, ancient sites and the longest sandy beaches in the Aegean. Naxos is very well connected with the Small Cyclades; Amorgos, Iraklia, Schinoussa, Pano & Kato Koufonissi and Donoussa. Until recently, these islands were very isolated so they still remain unspoilt… a small heaven of peace, Greek hospitality and traditional culture. Read our 10-day walking itinerary in the Small Cyclades…

Santorini (or Thira) is one of the most sought after holiday destinations for a good reason! It will take your breath away with its white Cycladic houses lining the cliff tops, the amazing views to the Caldera and Nea Kameni (the volcano), the spectacular sunsets, the excavated ancient cities, the black and red beaches… Few places in the world combine such amazing sceneries, beautiful beaches, ancient cities, gastronomical food, fabulous wine… and an active volcano!

You can combine the 10-day Naxos & the Small Cyclades walking itinerary with the following:


Day 1: Trail from Fira to Oia with incredible views of the caldera
Today we’ll take the trail that starts from the picturesque port of Fira and follows the rim of the caldera to Oia, passing the picturesque villages of Firostefani and Imerovigli. This hike is actually a spectacular, cliff-top walk with incredible views of the caldera, the volcano and the deep blue of the Aegean sea. This is the view that Santorini is so famous about and you will find out that you cannot get enough of it.

We will aim to reach Oia on time to watch the world famous sunset and then we will have supper at one of our favourite taverns where you will have the chance to try Santorini’s delicious dishes prepared with the local fine ingredients and also taste the local wine.

Day 2: Hike to the summit of Profitis Ilias, ancient Thera and Perissa beach
We’ll start the hike from the traditional reservation of Emborio. The trail looks like a gorge as it goes up in between two hills and underneath two arches. As you admire the beautiful vineyards on the slopes towards Akrotiri you will soon reach the 567m summit of Profitis Ilias. We’ll stop at the monastery for a snack and a rest.

We’ll then walk through a magnificent mountainous landscape from Profitis Ilias towards ancient Thera, a must see! The excavations show remnants of houses, a small theatre, Roman baths, cisterns, a holy road e.t.c., dated from the 9th century AD until the Roman time. We will finally take the path leading to the beach of Perissa, admiring the spectacular views and we’ll end the day with a beautiful supper by the beach.

Day 3: Day trip to the Volcano, hot springs & Thirasia
We’ll take the boat to the volcano and walk the short, dusty path to the active crater. You will be stepping on the newest volcanic island in the East Mediterranean and you will see large pieces of magma. Next, we will head towards the hot springs where you can enjoy swimming in the sulphurous springs of the volcano.

We will then continue to the small island of Thirasia which, although so close to Thira, remains totally unspoilt by tourism. You can choose to stay by the beach or walk the 150 large and sloping steps to the village of Manolas to admire the magnificent views towards the caldera and Thira.

Day 4: Rest and explore
Today you can relax and explore the island’s numerous beaches such as the red or black beach. You can also visit the ancient city of Akrotiri which was buried after a volcanic explosion and has now been excavated. There are many options and we’ll be happy to advice you. We’ll end the day with a farewell supper with live Greek music and fine wine. 


Our recommended walks during the ‘Cyclades island hopping to Santorini’ walking holiday are graded as easy to moderate. We will walk mainly on paths of easy or moderate gradient with ascents of up to 500m in a day. We will walk up to 4-5 hours in the day including stops to rest and for lunch. Being predominately limestone some parts of our paths can be quite rough and stoney.

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. 10 and 14 day itineraries are offered as well as a self-guided option.

Solo travellers are welcome. It’s always more fun to walk with a group of like-minded travellers.


We organise our ‘Cyclades island hopping to Santorini’ 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 island hopping to Santorini’ walking holiday unforgettable for you.

green_bullet Check our fees!

green_bullet How we walk towards nofootprint…

green_bullet Check photos from this walking holiday to Santorini…