Hiking the Cyclades - Naxos & Santorini

You arrive at Santorini airport and take a taxi to the harbor, where the ferry awaits for the approximately two-hour crossing to Naxos. From the harbor it's just a short journey to the hotel, where you check in before heading out to explore the town. If you arrive early in the day, you can stretch your legs with an approximately 1.5-hour warm-up hike to Chrisostomos – a perfect introduction to the trip with beautiful views over the landscape. If you arrive late in the day and miss the ferry to Naxos, you spend the first night on Santorini.

The day begins with local bus or taxi to Chalki, in the heart of the Tragea plain. From here you hike straight into central Naxos' fertile agricultural landscape, surrounded by lush greenery and ancient olive groves with trees over a thousand years old. You follow stone-paved paths up to the Venetian fort Ano Kastro and continue to a historic marble quarry where a ten-meter-high statue from the 6th century BC still stands guard. You can choose to shorten the day by ending the hike in nearby Melanes and taking a taxi or local bus back to the hotel. Alternatively, you continue via the village of Potamia – whose name means "river" in Greek – through green valleys back to Chalki via Ano Kastro.

A short transfer takes you to Kynidaros, from where you follow an easy and pleasant trail to the small village of Eggares. Here you'll find photogenic churches and two restored olive presses, one of which dates from 1885. You'll learn more about the sacred art of olive oil production and enjoy a local lunch at a taverna by the charming square, beautifully built in stone. Afterwards you hike back to the hotel.

You take local bus or taxi to Filoti, and already at the start you're met with an impressive sight: the village lies right below Mount Zas, also known as Zeus mountain. Today's great challenge is the ascent of this mythical mountain. The hike up is demanding but the reward is magnificent, with panoramic views over Naxos and the surrounding islands. After the summit you hike down again and continue through cultivated fields and past a monastery before reaching Apiranthos, one of Naxos' largest villages. Here it's perfect to take a break at a local café before taking a taxi or bus back to Naxos Chora.

Take it easy in the morning and take the opportunity to visit the castle and museum in Naxos Chora. Afterwards the hotel arranges transfer to the harbor where you board the ferry at 1:00 PM for the approximately 2.5-hour journey to Santorini. When the ferry glides into the sunken volcanic crater you're met by dramatically steep, color-shifting cliffs crowned by whitewashed villages - one of the Mediterranean's most iconic views. It was here that the violent volcanic eruption about 3,600 years ago is believed to have contributed to the fall of the Minoan civilization – and possibly given rise to the myth of Atlantis. The ancient excavation site Akrotiri is within walking distance of the hotel, as is an optional short circular walk along the crater rim.

A short transfer takes you to the resort town of Perissa. From here you follow an old path up through open and exposed landscape to an area that existed even before the devastating volcanic eruption. You hike up to Ancient Thira, the island's capital during ancient and Roman times – today a fascinating maze of ruins with magnificent views over the sea. Then the hike goes down towards quiet inland environments among small vineyards and peaceful villages. The landscape is a patchwork of volcanic shapes and colors, and in the afternoon sun you slowly make your way back to the village of Akrotiri.

You take local bus to Fira, Santorini's capital, and stroll through a charming maze of narrow whitewashed alleys that cling to the cliff edge above the caldera. Visit the museum dedicated to Ancient Thira and the archaeological museum before enjoying a good and energizing lunch. In the afternoon awaits one of Greece's most classic hikes – the trail from Fira to Oia. The path follows a well-maintained old mule track with constant views over the lagoon and the dramatically steep cliffs. In Oia you're picked up for transfer back to the hotel.

If you have a flight in the afternoon or evening there's an opportunity to walk to the nearby archaeological site Akrotiri, often called Greece's Pompeii. You can also extend the hike from Ancient Akrotiri to Red Beach and – if the tide allows – continue to Black Beach. Then you follow a gravel road inland to Loumarades, one of the island's most authentic areas. The final stretch goes through vineyards and terraced farmland back to Akrotiri via the Venetian fort.

The trip ends with a short transfer to Santorini airport.