Blue domes on the island of Santorini in the Cyclades
Blue domes on the island of Santorini in the Cyclades

The Cyclades: Naxos & Santorini

68 km
8 days | 7 nights
Apr May Jun Jul Aug Sep Oct
price from
€ 638
CO2 footprint
246 Kg/person
  1. Greece
  2.  | 
  3. Self-Guided
  4.  | 
  5. Tourcode GRSW016

This journey includes two among the most beautiful islands of the Cyclades: Naxos, the island of contrasts, and Santorini, which do not need presentation. One week though green olive-orchards and the sharp contrast of deep blue Aegean Sea, which you will be able to enjoy from the summit of Mount Zas.

You will discover the beauties of Naxos,the place where as the Greek mith tells Theseus abandoned Arianna: in this island, the biggest of the Cyclades, a lively night life coexists with heartfelt traditions.

Santorini feels like no other place on heart: the whitewashed cube-shaped houses and bright blue doors and windos is famous worldwide. You will discover its secrets walking slowly through the narrow paved streets and steep cliffs, result of an explosion of the Thira Volcano thousands of years ago.

To crown it all, you will enjoy the signature flavours of Greek kitchen: dishes based on fresh fish, seasoned with olive oil, a real local specialty.

IMPORTANT: Flight requirements for this itinerary: Arrival before 13:00 at Santorini Airport 


  • Lose yourself among the narrow paved streets of Greek villages;
  • Enjoy a spectacular sunset on the sea;
  • Discover Akrotiri, the Greek Pompei;
  • Immerse yourself in the fascination of Greek myths, from Zeus to the ancient city of Atlantis.


Day 1

Arrival in Santorini; boat to Naxos

Arrival in Santorini; boat to Naxos

Your trip starts at Santorini airport where you will be met by a taxi which will take you to the port for your ferry to Naxos. The ferry journey between the islands takes two hours. On Naxos you will be met at the port and taken to your hotel. If the day time allows you to do so, you can make the 1,5 hour walk to Chrisostomos starting from the port. This way you get to know the town and will admire great views over Chora whilst stretching your legs.  

If your flight arrives too late for the ferry to Naxos and you outbound flight is after 6 pm, you will stay first in Santorini and then in Naxos. 

Day 2

Loop from Chalki, 10 km or 14 km or 19 km

Loop from Chalki, 10 km or 14 km or 19 km

A bus will take you to Chalki, located in the center of the Tragea plain. Today you explore this fertile inner land of Naxos, with secular olive trees and rich vegetation. You will walk on cobblet paths to the majestic statue of an unfinished Korous from the 6th century BC. Along your way you will find the fortified hamlet of Kastro. The walk ends in Melanes, where a bus will take you back to the hotel.

Distance: 10, 14 or 19 Km

Ascent/descent: +150, 300 or 400/-150 or -300 m

Day 3

Walk from Kynidaros to Eggares, 7 km

Walk from Kynidaros to Eggares, 7 km

After a short transfer to Kynidaros, enjoy a gentle walk to the small village of Eggares. Explore its picturesque churches and two restored olive presses one of which dates back to 1885.  Enjoy lunch in one of the tavernas on the stone- built main square before returning to your hotel. Visit of the olive press in Eggares    

Distance: 7 Km

Ascent/descent: +100/-400 m

Day 4

Walk from Filoti to Apiranthos via Mt Zas, 12 km

Walk from Filoti to Apiranthos via Mt Zas, 12 km

Today you will take another public bus or taxi to the village of Filoti to start today's walk. From the village, built at the foothills of Mt. Zas (also known as Mount Zeus), you climb to the summit of this legendary mountain. Upon reaching the summit, you will be rewarded with panoramic views of Naxos and the surrounding islands. After descending back down, you walk through agricultural fields and along a monastery to the village Apiranthos one of the biggest villages on Naxos.

After a relaxing break in a local café, you can take a taxi or public bus back to Naxos Chora.

Distance: 12 Km

Ascent/descent: +650/-650 m

Day 5

From Naxos to Santorini, 7.3 km

From Naxos to Santorini, 7.3 km

Today you will travel from Naxos to Santorini. In the morning you may visit the Castle in Naxos town (Chora) and the museum and enjoy a relaxing morning.   The hotel bus will take you to the port of Naxos. The ferry usually departs around one o’clock and arrives two and a half hours later on Santorini. As the ferry arrives through the submersed volcano crater you will be impressed by the views to the steep coloured cliffs of this ancient volcanic island and the whitewashed villages on top. It is said that the eruption that happened here 3,600 years ago, ended the Minoan Civilization. It may also have been the source for the legend of Atlantis.  You may walk a short round walk from Akrotiri along the caldera or you visit Akrotiri Ancient Site that is within walking distance from your hotel. 

Distance: 7,3 Km

Ascent/descent: +240/-240 m

Day 6

Walk from Perissa to Akrotiri, 13 km

Walk from Perissa to Akrotiri, 13 km

Today a transfer will take you to Perissa, from where you start climbing via an old path to an exposed saddle. This part of the island is one of the very few places that pre-dates the devastating volcanic eruption. First you walk up to Ancient Thira - the capital of the island in Ancient and Roman times, then descend via an old path to the quiet interior of the island, walking through vineyards and through picturesque villages. Continuing through the volcanic landscape, you walk back to Akrotiri village.  

Distance: 13 Km

Ascent/descent: +580/-550 m

Day 7

Walk from Fira to Oia, 10.3 km

Walk from Fira to Oia, 10.3 km

This morning you will catch a public bus to Fira, the capital of Santorini. Here you can explore the narrow alleyways of this whitewashed town, built on the top of the volcanic cliffs. You may also wish to visit the museum of prehistoric Thira and the Archaeological Museum. In the afternoon, you make the famous walk from Fira to Oia. You will mainly walk along a well-maintained mule-path with fabulous views of the lagoon and the spectacular steep cliffs. When you reach the small town of Oia you will be picked up and transferred back to your hotel. 

Distance: 10,3 Km

Ascent/descent: +300/-400 m

Day 8

Holiday ends in Santorini

Holiday ends in Santorini

A transfer will bring you from the hotel to the Santorini airport. 


Is this for me?

If you have always dreamed of visiting Santorini, this trip will take you there and to Naxos, the largest island of the Cyclades. The hikes offer continuous moments of wonder - a great view over the gulf, walking between the olive groves, remains of ancient cities. If you'd like to enjoy the sea, you can add a couple of rest days before or after the trip. 


What is included

  • 7 Nights in double room in **/*** hotels with breakfast
  • Ferry tickets Santorini-Naxos and Naxos-Santorini
  • All transfers as described in the day by day program
  • maps and detailed description of the itinerary
  • Medical and luggage travel insurance
  • 24h phone assistance

What is not included 

  • Transfers to the starting location and from the arriving location of the tour
  • lunches and dinners, if not otherwise stated
  • visits and entrance fees - tips
  • personal expense
  • possible sojourn taxes
  • everything that is not mentioned in the "What is included" section.

Optional Services

These services can be added to the ones included in the base price of the tour:

  • Single room supplement
  • cancellation insurance
  • Transfers to reach the starting location or to leave the arriving location of the tour, which will be quoted on request.


We work with 3* hotels, B&Bs and farmhouses that reflect our way of experiencing travel: they are comfortable and characterful structures, which we choose one by one, managed by passionate and welcoming people.

Unless otherwise specified in the travel listing, all provide private en-suite rooms with breakfast included.


Naxos Resort Beach Hotel Naxos
Hotel Anixis - Naxos
Kalimera Hotel Santorini
Kalimera Hotel - Santorini

What to bring

Clothing and other items
You will need your regular walking/cycling gear, including some sort of reflective garment. For the evenings, smart outdoor style trousers (or shorts) are invaluable, as are quick-dry t-shirts. These can be washed easily and will dry overnight and still look good for sightseeing or having a drink in town.

Take as little as possible to avoid potentially lugging a heavy suitcase up three flights of stairs at the end of the day. Please be aware that laundromats (“Laverie”) are not common in rural areas, so plan to do handwashing of small items.

Lightweight walking shoes/ trainers
For wearing around towns & villages. They can also be a back-up pair.

Socks & underwear
Take only good quality socks with quick-dry and insulating qualities. Road test them before you go on the trip. Take a suitable quantity of underwear as washing facilities are limited.

Warm jacket, hat, gloves
Bring a fleece, Polartec or warm layers for the evenings especially in spring or autumn; be sure it is totally suitable for your needs.
A fleece jacket which blocks the wind (Wind-stopper) is the most preferable. In the summer months a lightweight jacket is suitable for evenings.
If you are cycling/walking in mountainous or coastal areas, even in the height of summer, the weather can change very quickly and unexpectedly and you should be prepared for fog, mist, rain, snow or hail at any time. Always take an extra layer with you, as well as a warm hat and gloves.

Waterproof jacket & trousers
If you are caught in heavy rain, with good waterproof clothing you should remain dry. Remember that most garments will lose their properties over time. Few will remain waterproof for more than five years and many deteriorate in three years or less. We recommend a rain jacket with a good hood and collar and waterproof or thermal walking/cycling trousers or tights.

Dress code
In general, you should wear suitable clothing when entering a church (in many places, it is considered unacceptable to go inside wearing shorts or a tank-top). We suggest that women carry a shawl to cover up bear shoulders or low-cut tops. It also comes in handy when your shoulders get sunburned!

It is considered inappropriate for men to go without a shirt / T-shirt (other than at the beach).

Trekking poles (adjustable)
Highly recommended. A pair works best, depending on what you are comfortable with. If you suffer from back or knee pain this should be considered essential. Remember to practise walking with your pole(s) on different types of terrain in the months preceding your trip.

Walking boots
The importance of good footwear cannot be stressed enough. Your boots should be sturdy and of good enough quality to handle all types of terrain. Lightweight boots, (cordura/leather boots) which have Gore-Tex or sympatex water-proofing are most suitable for this trip. They should provide good ankle protection and be well broken in. Waxing leather boots regularly prolongs their life.

Walking tops & trousers
We recommend walking trousers and shorts and quick-dry wicking t-shirts. These can be washed easily and will dry overnight and still look good for sightseeing or having a drink in town. Wicking T-shirts are fast drying, keep moisture away from your skin and are available at outdoor stores. You should also bring one pair of loose-fitting trousers to wear in cities and for evenings out, etc. Shorts or zip-off trousers are useful in warmer weather.

Practical info

How to arrive

You will travel in and out from Santorini airport. If your flight arrives before 14:30 hrs., you will be transferred to Piraeus port and travel on the 17:30 hrs. ferry to Naxos (duration of the ferry is app. 5,5 hrs). 
If you arrive after 14:30 hrs, you will travel to Santorini center by public transport or taxi, and will be transferred to Piraeus the next day in the early morning.

Your transfer from Piraeus port to your hotel in Santorini at the end of your trip is included. You will travel by public transport or taxi from Santorini to the airport on your departure day.

Mobile App

Use the SloWays APP for iOS and Android smart phones in combination with the written documentation provided.

The App has the detailed tracks and maps that you can use offline and without roaming. Thanks to the phone’s internal GPS, you can check your exact position on the map, so you always know exactly where you are. It also helps you self-navigate you way while travelling. More information on how to use the App inside the roadbook documents.

The navigation features include:

  • Offline navigation. Mobile data not required after initial download
  • Accurate GPS tracks
  • Autorotation of the maps
  • Daily route summary and elevation chart
  • Panorama of the track and at street level
  • Alarm and vibration that alerts you in case you go off track.
  • Emergency SMS button with position coordinates
  • Possibility to record and take georeferenced photos of problems on route alerting fellow travelers
  • Hotel information
  • Points of interest along the way
  • Historical background

Wanderlust Nominee Best Specialist Tour Operator 2023
Nominee Best Specialist Tour Operator 2023
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Borgo Allegri 16R
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P. IVA 05227330486

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