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Jewels of the Cyclades: Naxos and Santorini 11

Jewels of the Cyclades: Walking on Naxos and Santorini


Discover the iconic Naxos and Santorini, two of the Cyclades’ most beautiful islands, 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 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 the 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

Click to view map


Day 1: Arrival in 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.

*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 | 14 km

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 to 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: Anixis Hotel

Day 3: Walk from Kynidaros to Eggares | 7 km

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 lunch in one of the main square taverns.

  • Walking for the day: approx 2.5 hrs, 7km, ­↑100m ↓400m
  • Accommodation: Anixis Hotel

Day 4: Walk from Filoti to Apiranthos via Mt. Zas | 12 km

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 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: Anixis Hotel

Day 5: From Naxos to Santorini | 7.5 km

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 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 within 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 | 13 km

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 island’s quiet interior, 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 | 10.5 km

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 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 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 then 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.

What to Expect


Accommodation is in nice 2/3-star hotels in double or twin private en-suite rooms. 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.

Click to view default hotels

*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 the route, lunches and snacks should either be bought from local shops, or packed lunch can be pre-ordered from your hotel the night before. You can have dinner at your hotel or nearby restaurants and taverns.

Difficulty & terrain

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). We strongly advise you to follow only marked trails and never 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 September/October. Our recommended periods are spring (when nature is at its best) or early autumn (when the seawater temperature is still enjoyable). Naxos and Santorini’s climate is typically the 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 rarely 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 can make the air feel cooler than it is and make the sea rough. The flexibility of self guided holidays means that there are no fixed dates, and you can start your trip on any date during the season.

Getting there

FCO up-to-date travel advice

Our recommended airport for this tour is Santorini (JTR).



  • 7 nights accommodation on a bed & breakfast basis in 2/3-star quality hotels (4 nights on Naxos and 3 nights on Santorini)
  • 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
  • Detailed digital holiday information pack including GPS-checked and regularly updated route descriptions, road notes and maps. Please note that the info pack is emailed to you prior to departure and no printed documents are mailed or provided on-site.
  • 24/7 phone support by our local office/representative


  • Airfare and connecting land transfers
  • Public transport Akrotiri – Fira
  • Transport from/to the walks on Naxos (public transport or taxi)
  • Lunches, dinners, drinks and snacks
  • Travel insurance (required – get a quote online)
  • Personal expenses
  • Local tourist taxes and entry fees (payable on-site)
  • Any items not explicitly listed as included

Options, extras & supplements

  • Single room supplement applies to members of a group who require a single room
  • This holiday is available for solo travellers; a supplement will be charged as accommodation and luggage transfer costs are not shared (we never mix and match – solo travellers will be accommodated in single rooms)
  • Extra nights in Santorini or Naxos
  • Transfer to Fira on day 7 of the programme