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Jewels of the Cyclades: Naxos and Santorini, walking holidays in Greece, Greece walking holidays

The Natural Adventure Company

Self Guided Walking Holidays and Cycling Holidays

Jewels of the Cyclades: Naxos and Santorini


Jewels of the Cyclades: Naxos and Santorini, walking holidays in Greece, Greece walking holidays
Average rating:   5,  1 reviews
Activity type
Self Guided Walking
8 days & 7 nights
March - October


Day 1: Naxos
Day 2: Chalki
Day 3: Eggares
Day 4: Filoti
Day 5: Santorini
Day 6: Akrotiri
Day 7: Fira
Day 8: Departure

Overview for Jewels of the Cyclades: Naxos and Santorini

Discover the iconic Naxos and Santorini, two of the most beautiful islands of the Cyclades, on a week-long walking adventure at your own pace.

The largest of the Cyclades, Naxos was a cultural centre of Classical Greece and Byzantium, and later Venetian and Frankish influences also left their mark. During the first part of your trip you will discover the enchanting villages of Chalki and Melanes, walking along cobbled paths through ancient olive groves. You will also explore the legendary mount Zas and its highest peak (1,000 m) overseeing the Cyclades.

After a two-hour ferry transfer, the second part of the itinerary will reveal to you another Greek landmark destination: the island of Santorini. With its ancient history, authentic villages, excellent wineries and breathtaking views, Santorini is topping every traveller’s destination hit list for a reason!


  • Enjoy panoramic views of the Cyclades from summit of Mt. Zas (1,000 m)
  • Marvel at the Kouros statues on Naxos, 2,800 years old
  • Follow unique cobbled paths on ancient trails across the islands
  • Visit the iconic cliff-top villages of Santorini perched high above the breath-taking caldera
  • Visit the ancient sites of Thira and Akrotiri on Santorini

Itinerary for Jewels of the Cyclades: Naxos and Santorini

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Day 1: Arrival at Santorini and travel to Naxos

When you arrive at Santorini airport you will be met by a taxi which will take you to the port for your ferry journey to Naxos, taking approximately two hours. In Naxos you will be met at the port and transferred to your hotel. Depending on the timing you can go for a 1.5 hour walk to Chrisostomos, getting to know the town and admire the views of Chora and stretching your legs after the boat ride.

Accommodation: Naxos Resort

*Note that if your flight arrives too late for the ferry to Naxos you will stay in Santorini on the arrival day. It is recommended to arrive before 1 pm so you can take the maximum of your day. The itinerary can also be reversed on request if this better fits your flight schedule.

Day 2: Round walk from Chalki via Melanes

You take either a local bus or a local taxi to Chalki to the heart of the Tragea plain from where you will explore the fertile countryside of central Naxos, covered with olive groves and rich vegetation. You walk on cobbled paths via the Venetian Fortress, Ano Kastro, to an ancient marble quarry where you find a 10m high statue dating back to the 6th century BC. You may end your walk in the nearby village Melanes from where you can take either a taxi or local bus back to the hotel. If you continue, you will reach the village of Potamia (meaning river in Greek), and walk back via Ano Kastro to Chalki.

Walking for the day: approx 4.5 hrs, 14km, ­↑300m ↓300m
Accommodation: Naxos Resort

Day 3: Walk from Kynidaros to Eggares

A short transfer takes you to Kynidaros for the start of a gentle walk to the small village of Eggares, where you can explore its picturesque churches and two restored olive presses one of which dates back to 1885. Before returning to your hotel you can enjoy a lunch in one of the taverns on the main square.

Walking for the day: approx 2.5 hrs, 7km, ­↑100m ↓400m
Accommodation: Naxos Resort

Day 4: Walk from Filoti to Apiranthos via Mt. Zas

Today you take another public bus or taxi to the village of Filoti for the start of the walk. From the village, built at the foothills of Mt. Zas (also known as Mount Zeus), you climb to the summit of the legendary mountain. As you reach the summit, you will be rewarded with panoramic views of Naxos and the surrounding islands. After reaching the top, you will descend through fertile fields, passing by a monastery and reaching Apiranthos, one of the biggest villages on Naxos. After relaxing at some of the local cafés, you can take a taxi or public bus back to your hotel.

Walking for the day: approx 4 hrs, 12km, ­↑650m ↓650m
Accommodation: Naxos Resort

Day 5: From Naxos to Santorini

Today you travel from Naxos to Santorini. In the morning you may visit the Castle in Naxos town (Chora) and the
museum. The hotel shuttle will take you to the port of Naxos. The ferry cruise usually departs around one o’clock and takes approximately  two and a half hours. As the ferry arrives through the submersed volcano crater you will be impressed by the views of the steep cliffs of the ancient island and the whitewashed villages on the top. It is believed that the eruption that happened here 3,600 years ago ended the Minoan Civilization. As you arrive, you may go for a short round walk from Akrotiri along the caldera or visit the Akrotiri ancient site that is within a walking distance from your hotel.

Walking for the day: approx 2.5 hrs, 7.5 km, ­↑240m ↓240m
Accommodation: Kalimera Hotel

Day 6: Walk from Perissa to Akrotiri

In the morning a transfer will take you to Perissa, from where you start climbing on an old path to one of the very few parts of the island unaffected by the devastating volcanic eruption. You walk up to Thira, the ancient capital of the island, and then descend on an old path to the quiet interior of the island, walking through vineyards and picturesque villages. Continuing through the volcanic landscape, you walk back to Akrotiri village.

Walking for the day: approx 5.5 hrs, 13 km, ­↑580m ↓550m
Accommodation: Kalimera Hotel

Day 7: Walk from Fira to Oia

Today you catch a public bus to Fira, the capital of Santorini, where you can explore the narrow alleyways of the whitewashed town built on the top of the volcanic cliffs. You may also visit the museum of prehistoric Thira and the Archaeological Museum. In the afternoon, you take on the famous path from Fira to Oia. For most of the time you walk on a  well-maintained mule-path with fabulous views of the lagoon and the spectacular steep cliffs. As you reach the small town of Oia, you will be picked up and transferred back to your hotel.

Walking for the day: approx 3 hrs, 10.5 km, ­↑300m ↓400m
Accommodation: Kalimera Hotel

Day 8 Departure

Depending on your departure time, you may go for a short walk to the nearby archaeological site of Akrotiri – the Greek Pompeii that opened for visitors in 2012 after it had been closed for many years. You can extend the walk from to the red beach and then to the black beach if the waves allow you to pass. From there, you walk inland on a dirt road taking you to one of the most authentic parts of Santorini, Loumarades. You than follow paths through vineyards and scenic terraces back to Akrotiri. You will pass through the Venetian Fortress in the village before coming back to your hotel. Your trip ends today after a short transfer to Santorini airport.

Hotels for Jewels of the Cyclades: Naxos and Santorini

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3-star hotels including breakfast every morning. We have carefully hand-picked all places and regularly monitor their quality. We have tried to choose accommodations that offer friendly service, clean and comfortable rooms and local flavour.

Sample Hotels*: Naxos Resort, Kalimera Hotel

*Hotels are subject to availability. In case a particular hotel is fully booked for your desired dates, we will replace it with a hotel of equal value and quality level. We will provide exact accommodation details to you upon booking confirmation.


Breakfasts are included on all days. When no restaurant location is available on route, lunches and snacks should either be bought from local shops, or packed lunch can be pre-ordered from your hotel the night before.

Travel for Jewels of the Cyclades: Naxos and Santorini

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By Plane

Our recommended arrival airport for this holiday is the one in Santorini, from where you have a transfer pickup included in your package.

Baggage Transfers

Baggage transfers during all walks are included and your bags will be transferred by your current hotel (or by private transfer) to your next hotel.

Country Info

Timezone: GMT +2

Language: Greek. In big cities, many people speak English, but in remote areas, this might not be the case. However, most of the hotel personnel where we stay speak English and are ready to help you. Road signs/markers are normally in both Greek and Latin alphabet – and you can always call our 24/7 helpline if there are any problems.

Electric supply and plugs: 220V, 50Hz, two-pin round plugs.

Currency: Euro (€). We strongly advise taking adequate cash for your daily requirements. Banks and ATMs are not available outside of big towns but credit/debit card payments are accepted in most places.

Cost of living: in Greece it is cheaper than in the UK. Some sample prices follow:

  • A 3-course meal in a standard restaurant: 12€
  • A litre of mineral water from a street shop: 1€
  • A cup of coffee: 2.5€

Up-to-date travel advice on Greece is available here.

Detailed up-to-date travel information and hints will be provided in your holiday information pack.

Trip Info for Jewels of the Cyclades: Naxos and Santorini

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Difficulty Grade: Moderate

Some of the paths take up to 5-6 hours of walking and have some steep sections. This holiday is appropriate for experienced walkers and requires a  good level of fitness in order to enjoy the walking sections to the maximum (read more about difficulty grades).

Route Navigation

We strongly advise you to follow only marked trails and never try to shorten the path through the unknown and unmarked terrain. We will provide you with detailed road notes and maps, and you can call our 24/7 local assistance phone number anytime. More detailed info on route navigation will be included in your holiday information pack.

When to Go

The best time to travel to the Greek islands is between April and June and in September/October. Our recommended periods are the spring time (when nature is at its best) or early autumn (when the sea water temperature is still very pleasant). In the summer months it gets very hot and overcrowded.

The flexibility of self-guided walking holidays means that there are no fixed dates and you can start your trip on any date in the season – so please indicate desired beginning date when booking


The climate of Naxos and Santorini is typically Mediterranean, with mild and rainy winters, and warm and sunny summers. The bulk of the rain falls from October to March; in the summer it almost never rains.

In the warm season, starting from May, the Cyclades are particularly affected by the Meltemi, a wind that blows from the north, persistently and in periods lasting a few days. This wind is able to make the air feel cooler than it is and make the sea rough.

What to Bring

We recommend that you travel as light as possible – airlines might charge you an extra fee, and during ground transfers, the place might be limited. Ideally, you should bring one piece of luggage weighing not more than 20 kg (to be checked in) and a daily pack (15 – 20 l rucksack) for your everyday essentials (snacks, drinking water, camera, etc.). Below is a non-exclusive list of what you should bring to this trip. More detailed info will be included in your holiday information pack. If you need further advice, please contact a reputable outdoor retailer or us.

  • Good hiking boots
  • Hiking socks
  • Several t-shirts (cotton or preferably breathable/fast drying)
  • Packable waterproof and windproof jacket with hood
  • Synthetic mid layer or warm fleece
  • Trainers and/or sandals – to relax and wear inside accommodation
  • Sunglasses, sunscreen and lip salve
  • Hat/Baseball cap
  • Personal First Aid kit (wet wipes, flu remedies, stomach remedies)

Included for Jewels of the Cyclades: Naxos and Santorini

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  • Detailed route description and maps in English
  • 7 nights accommodation on a bed & breakfast basis in 3-star quality hotels (4 nights on Naxos and 3 nights on
  • Transfer Santorini Airport – Santorini port
  • The round-trip transfers on Naxos and Santorini listed in the itinerary
  • Taxi transfer Akrotiri-Perissa and Oia-Akrotiri (Santorini)
  • All necessary ferry tickets in tourist class
  • Original walking map of Naxos and Santorini (Orama, Anavasi or Road Editions)
  • 24/7 phone support by our local office / representative

Note that there is an additional tourist tax of 1,50 EUR per room for each night, payable upon arrival in your hotel

Single Room & Solo Traveller Supplements

  • Where individual members of a group require a single room, a single room supplement is applicable.
  • This holiday is available for solo travellers. As costs are not shared, a supplement is payable on the standard trip cost.

Please click the CHECK AVAILABILITY button above to see the price of the holiday and the different options, extras and supplements for your desired dates.


  • Flights to and from Santorini
  • Public transport Akrotiri – Fira town
  • Transport from/to the walks on Naxos (public transport or taxi)
  • Travel insurance
  • Admissions and entrance fees of any kind
  • Tips and gratuities
  • Personal expenses such as lunches, drinks, phone calls, extra transfers etc.
  • Any items that have not been specifically mentioned in the program

Extensions and Optional Extras

  • Transfer to Fira on day 7 of the programme
  • Additional night/s at any of the accommodations in Santorini or Naxos
  • Hotel upgrades (upon request)

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Jewels of the Cyclades: Naxos and Santorini
Average rating:  
 1 reviews
by NIck C on Jewels of the Cyclades: Naxos and Santorini

We enjoyed exploring the islands and their ancient trails, especially Naxos. The holiday company were absolutely superb. Good communication prior to holiday, everything was booked perfectly and went without a hitch. Highly recommended.

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