Set off from Santorini Airport on a taxi transfer to the port, where you get a ferry for the two-hour journey to Naxos. It’s just a short ride from the port to your hotel, where you settle in then set out to see the town. If you arrive early in the day, stretch your legs on a 1,5-hour warm-up walk to Chrisostomos, an ideal introductory route with marvellous views. If you arrive late in the day and cannot get the ferry to Naxos, you’ll spend the first night on Santorini.

Challenge: 4.4 km, 1.5 hours, 130 m ascent, 130 m descent

Begin with either a local bus or taxi transfer to Chalki, smack dab in the heart of the Tragea Plain. Venturing out into central Naxos’ fertile countryside, you’re suddenly surrounded by rich vegetation and ancient olive groves with one-thousand-year-old trees! Clamber along cobbled paths to the Venetian fortress of Ano Kastro and an age-old marble quarry with a 10-metre-high statue from the 6th century BC. Shorten your day by ending the walk in nearby Melanes then get a taxi or local bus back to the hotel. Or press onward via the village of Potamia, ‘river’ in Greek, traversing lush valleys on your way back to Chalki via Ano Kastro.

Challenge: 10/14/19 km, 3.5/4.5/7 hours, 150/300/400 m ascent, 150/350/400 m descent

Short transfer to Kynidaros and gentle route to tiny Eggares, home to photogenic churches and two restored olive presses, one of which dates back to 1885. Learn the secrets of sacred olive oil production and savour a local lunch at a tavern on the main square, beautifully built in stone, before trekking back to your hotel.

Challenge: 7 km, 2.5 hours, 100 m ascent, 400 m descent

Take off for Filoti by public bus or taxi and smile at the start of your walk: a village built beneath Mt Zas (also known as Mount Zeus). Your challenge for the day? Climb to the summit of this legendary mountain! A tough endeavour rewarded by panoramic views of Naxos and its neighbouring islands. Stretch your legs the other way as you walk back down then hike past farmed fields and a monastery to reach Apiranthos, one of the largest towns on Naxos. Take a relaxing break at a local café then get a taxi or public bus back to Naxos Chora.

Challenge: 12 km, 4 hours, 650 m ascent, 650 m descent

Take it slow this morning and check out the castle and museum in Naxos Chora. Then get the hotel shuttle to the port and jump on the 13:00 ferry for the 2,5-hour crossing to the island of Santorini. Sailing into the submerged volcanic crater, you are greeted by impressively steep colourful cliffs crowned by pretty white-washed villages.
The violent eruption which occurred here 3600 years ago is said to have ended the Minoan Civilization. And may have produced the legendary lost city of Atlantis. Akrotiri’s ancient archaeological site is withing walking distance from your hotel, as is the optional short circular walk along the crater.

Challenge: 7.3 / 2.5 km, 2.5 / 1 hours, 240 / 150 m ascent, 240 / 150 m descent

A short transfer takes you to the beach town of Perissa, then you walk an old footpath up through open exposed terrain into a sector that pre-dates the devastating volcanic eruption. Trek up to Ancient Thira, the island’s capital in ancient and Roman times and nowadays a intricate maze of ruins offering immense sea views. Next you walk down into peaceful inland areas among tiny vineyards and quaint villages. Exploring further this intriguing volcanic patchwork of a landscape, you soak up the sun as you slowly make your way back to the village of Akrotiri.

Challenge: 13km, 5.5 hours, 580 m ascent, 550 m descent

Catch a public bus to Fira, Santorini’s capital, and get lost in its pleasing jumble of narrow white-washed lanes clinging to the top of volcanic cliffs. Travel back in time at the museum dedicated to Ancient Thira and inspect the displays at the local Archaeological Museum. Then revel in a tasty energetic lunch and get ready for this afternoon’s jaunt: walking the famous route from Fira to Oia. Marching along a well-maintained mule path, you thrill to fabulous views of the lagoon and spectacularly steep cliffs. When you reach the small town of Oia, you’ll be picked up for the transfer back to your hotel.

Challenge: 10.3 km, 3 hours, 300 m ascent, 400 m descent

If you have an afternoon or evening flight, you might walk to the nearby archaeological site of Akrotiri, the Greek ‘Pompeii’ which re-opened in 2012 after many years closed. Option of extending the route from Ancient Akrotiri to ‘Red Beach’ and -if the tide is out- ‘Black Beach’. Next you take a dirt track inland to one of the most authentic parts of the island, Loumarades. The last section traverses vineyards and farmed terraces, leading back to Akrotiri via the Venetian Fortress.

Your trip comes to an end with a short transfer to Santorini Airport.