Walking on the Greek Islands

Discover the most scenic trails on the Cyclades trio of Santorini, Naxos and Paros with a local tour leader

Walking on the Greek Islands

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Trip Fee

$ 2.400

Single Room Difference

$ 570

Date

28 September - 05 October 2025

Trip Information

When you think of the Greek islands, it’s the Cyclades that spring to mind, with their white-washed houses and blue-domed churches set against the cobalt Aegean Sea. They’re beauty is striking, but even more so with our expert local tour leader guiding you along their most scenic trails. So, join us on this small-group hiking adventure on Santorini, Naxos and Paros and enjoy a relaxed week of hiking through picturesque villages, lush valleys and sandy beaches. Better yet, it starts and ends in Athens, giving you the opportunity to add extra days onto the itinerary and explore the birthplace of democracy.

Activity Areas

Coastal Walks
Walking & Trekking

Region & Country & City

Europe: Greece, Greek Islands

Included in the Price

— All breakfasts — All accommodation — All transport and listed activities — Tour leader throughout — Group arrival and departure transfers available

Not Included In The Price

— Travel insurance — Single accommodation (available on request) — Visas or vaccinations — Tourist tax (paid locally)

Accommodation Information

— Accommodation: 7 Classic nights (hotels) — Three full days and two half days of hiking on three islands — Travel by public transport, boat/ferry, and coach — Group normally 4 to 16, plus leader. Minimum age: 16

Map

Itinerary

Day 1 Start Rafina

Our adventure begins in Rafina, a port town around 25 minutes’ drive from Athens, the history-soaked capital of Greece. The excitement builds with a welcoming briefing at 8pm, in which the tour leader provides important information about the week ahead. Rest well tonight, tomorrow we wake early to catch a ferry. If you’d like to explore the many ancient wonders of Athens, we highly recommend adding extra days to the beginning or end of the main itinerary. Speak to your sales representative to book.

Day 2 Ferry to Santorini; explore Fira town

Take the ferry (approximately eight hours) to Santorini in the morning. There’s a selection of restaurants and cafes on board, serving throughout the journey. Santorini (known locally as Thira) is a remnant of a volcanic cone whose top was blown off and many speculate it was the location of the legendary lost Atlantis. This beautiful island has a lot to offer to hikers, including excellent beaches and magnificent views of the Aegean Sea. Walk around the town of Fira in the late afternoon, taking a flat paved path to enjoy stunning views of the caldera. Accommodation: Hotel Golden Star (or similar)

Day 3 Hike the caldera from Fira to Oia

The 6mi (10km) Cliff Trail is a spectacular walk, 1,310ft (400m) high above the volcanic caldera, a photographer’s delight and not too challenging. Half the path is pathed, while the other is a mix of volcanic soil, pumice and lava. Views of the Aegean are virtually ever present as we wind gently up and down to the pretty village of Oia, home to artists, galleries, boutiques and cafes. There’s time to explore, relax and soak up the culture before a transfer back to Fira. Accommodation: Hotel Golden Star (or similar)

Day 4 Free time in Santorini; afternoon ferry to Naxos

Enjoy free time in Santorini this morning. Optional excursions include a visit by bus to the buried city of Acrotiri, time at the black beaches of Kamari and/or a visit to the prehistoric museum of Thero in town. Leaving Santorini in the afternoon, we board the approximately two-hour ferry to Naxos. Accommodation: Hotel Aeolis (or similar)

Day 5 Hike through the lush Tragea Valley

Transfer (one hour) to hike in the lush Tragea Valley, best known for ancient olive and citrus groves. It is a great opportunity to discover the most authentic part of Naxos, where picturesque villages and churches punctuate our walk. Wander along the ancient stoney path in the middle of the Naxian marble quarries until we reach Kouros, a gigantic statue from the fifth century BCE, which was damaged during transportation and then abandoned ever since, lying under trees in the Melanes Valley. Our transfer back is approximately one hour. Accommodation: Hotel Aeolis (or similar)

Day 6 Ferry to Paros; hike the Byzantine path from Lefkes; return to Naxos

Take a one-hour ferry to Paros in the morning, then a 20-minute bus to the heart of the island and Lefkes village, where we join an Old Byzantine path that runs all the way to the east coast of Paros. The route, which is on paved path and over small hills, is believed to be about 1,000 years old and used to traverse the entire island. Today’s trail passes through beautiful Cycladic and medieval villages. Then we explore the town, the castle and Byzantine Cathedral of Ekatontapyliani before our ferry back to Naxos in the evening. Accommodation: Hotel Aeolis (or similar)

Day 7 Explore Hora town; visit the Temple of Apollo

Take a walk to explore the main town, Hora, a Venetian Castello town. The market area is a delight to wander through, with craft shops, chapels and quaint restaurants. On the islet of Palatia stands the impressive Portara, an ancient marble gateway and the entrance to the remains of the Temple of Apollo. Accommodation: Hotel Aeolis (or similar)

Day 8 Ferry transfer to Piraeus; end Athens

Catch the ferry back to Piraeus or Rafina (approximately six hours) and transfer to Athens airport where the trip ends. Please note: the ferry port can change depending on the season.

Travel Dates

28 September - 05 October 2025 $ 2.400

12 - 19 October 2025 $ 2.325

26 October - 02 November 2025 $ 2.100

22 - 29 March 2026 $ 2.400

29 March - 05 April 2026 $ 2.400

12 - 19 April 2026 $ 2.400

19 - 26 April 2026 $ 2.400

04 - 11 May 2026 $ 2.400

17 - 24 May 2026 $ 2.400

24 - 31 May 2026 $ 2.400

27 September - 04 October 2026 $ 2.400

11 - 18 October 2026 $ 2.400

25 October - 01 November 2026 $ 2.400

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