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Walking on the Greek Islands route map

Our adventure begins in Rafina, a port town around 25 minutes’ drive from Athens, the history-soaked capital of Greece.Around 6pm, say yassou (hello) to your tour leader and fellow travellers, when we gather as a group to get to know each other and learn more about the adventures ahead. Your tour leader then ensures a big welcome by arranging a group dinner. 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. 

Meals: Dinner

Cross the water to Santorini this 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 paved path to enjoy stunning views of the caldera.From April to October, we take the five-hour catamaran to Santorini. From November to March, we use the eight-hour ferry.

Meals: Breakfast

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.Halfway along the trail, we stop for a picnic lunch in a small canteen with amazing views, where we enjoy fresh orange juice and freshly prepared Santorinian walnut and honey cake.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.

Meals: Breakfast

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.

Meals: Breakfast

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.There is time in the afternoon to swim from St George’s sandy beach, just five minutes from our hotel.

Meals: Breakfast

Take a 45-minute 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, passing through beautiful Cycladic and medieval villages. 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.We explore the town of Parikia, the castle and fourth-century Byzantine Cathedral before our ferry back to Naxos in the evening.

Meals: Breakfast

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. A visit to the famous cheese shop of Naxos and a century-old olive wood-burning bakery is a must – our tour leader treats us to warm bread and Naxian cheeses.After lunch in one of the seaside cafes in town, we visit a family-run pottery workshop to watch them make their creations and, if you’d like, purchase one of their pieces.On the islet of Palatia stands the impressive Portara, an ancient marble gateway and the entrance to the remains of the Temple of Apollo.

Meals: Breakfast

Catch the ferry back to Piraeus or Rafina (approximately six hours, please be aware that the ferry port can change depending on the season) and transfer to Athens International Airport where our adventure ends. Alternatively, speak to your sales representative about booking extra nights in the capital, giving you a chance to explore this history-soaked city at your own pace.

Meals: Breakfast

What’s included

Expert tour leader throughout to guide hikes and enhance the experience.
All breakfasts (7) and one group dinner included; breakfasts are simple Greek buffet-style (bread/toast, jam, juice, milk, local yoghurt, eggs, honey, coffee/tea) and in Santorini are served as an in-room basket breakfast.
7 nights in comfortable three-star hotels: 1 night in Rafina (Avra Hotel or similar), 2 nights in Santorini (Hotel Golden Star or similar), and 4 nights in Naxos (Hotel Aeolis or similar); family-run hotels are used on the islands.
All transport for the itinerary, including taxis, ferries/catamarans and coach transfers, plus group arrival and departure transfers at set times. Seasonal detail: Athens–Santorini is typically ~5 hours by catamaran (Apr–Oct) or ~8 hours by ferry (Nov–Mar).
Listed activities and guided walks with an expert local tour leader, including the Fira–Oia caldera hike on Santorini, Tragea Valley hike on Naxos, the Byzantine path on Paros, and explorations of Fira, Hora and the Portara.

What’s not included

International flights to and from Greece (Athens) are not included.
Travel insurance is not included and must be arranged by the traveller.
Visas and any required vaccinations are not included and must be arranged by the traveller.
Lunches and 6 dinners are not included unless otherwise specified.
Local tourist taxes payable at accommodations are not included.
Optional excursions and entrance fees during free time (e.g., Akrotiri, museums, beach visits) are not included.
Single room available on request for an additional cost (single supplement).

Additional information

Explore Fira on a guided stroll to walk the caldera rim in Fira, pausing at terraces where whitewashed houses and blue domes tumble towards the sea. The path is paved and easygoing, ideal for taking in the amphitheatre of cliffs and the cobalt sweep of the Aegean.

Learn how a colossal eruption shaped the volcanic caldera and the living culture that thrives on its rim. Frame photographs, listen for chapel bells, and pause for photos and reflection as evening light softens the lava rock and boats trace silver lines below.

Join a guided hike from Fira to Oia along cliffside paths high above the sea, crossing stretches of pumice and lava with constant Aegean panoramas. The route undulates beside volcanic caldera cliffs, offering sweeping viewpoints and time to breathe the thyme-scented air.

Break for a simple clifftop picnic of fresh orange juice and walnut-and-honey cake at a canteen overlooking the islands. Arrive in Oia to wander lanes of Cycladic houses and artists’ studios, where blue shutters and volcanic stone create a timeless island tableau.

Walk ancient paths through olive and citrus groves in Naxos’ Tragea Valley, passing whitewashed chapels and quiet hamlets perfumed with wild herbs. Stone lanes lead through pastoral landscapes where goat bells and breeze-stirred leaves set a gentle tempo.

Follow the story of the island’s famed Naxian marble quarries to a shaded glade where a reclining Archaic kouros lies unfinished among the pines. The route reveals traditional Cycladic villages shaped by centuries of stonecutting, olive tending and the rhythms of rural island life.

Walk the 1,000-year-old Byzantine path from Lefkes village towards the east, following flagstones between terraces, chapels and wind-shaped hills. This historic route crosses gentle rises, linking postcard Cycladic hamlets amid olive groves and dry-stone walls.

Later, explore the medieval Kastro of Parikia and step inside Panagia Ekatontapyliani, a fourth-century basilica central to Aegean Christianity. Hear how pilgrimage, marble trade and maritime power braided Paros’ story as Byzantine stonework, icons and sea breezes frame the old harbour.

Stroll the Venetian Kastro of Hora, threading through alleys of chapels, craft shops and family-run cafés. With your leader, sample Naxian cheeses and warm bakery bread from a century-old wood-fired oven, tasting the island’s pastoral heritage in every bite.

Visit a family-run pottery workshop to watch clay take shape, then cross the causeway to stand beneath the Portara, the marble gateway of the Temple of Apollo. Sea breezes, sunset light and harbour views complete this portrait of Naxos’ culture and coastline.

Visit the Bronze Age city of Akrotiri with a licensed guide, following elevated walkways above streets, houses and storerooms preserved for millennia. Hear how trade and craftsmanship flourished on Santorini before nature intervened.

See rooms encased in volcanic ash, sophisticated drainage and ceramics that reveal a cosmopolitan Aegean port. This is an optional experience at additional cost, bookable on tour with your leader during your time on Santorini.

Explore the Museum of Prehistoric Thera in Fira, where wall-paintings, Cycladic figurines and pottery from Akrotiri and nearby sites illuminate life before the great eruption. Exhibits reveal artistry, beliefs and trade links across the Aegean.

From elegant vessels to fresco fragments, each piece adds context to the island’s Bronze Age story. This is an optional experience at additional cost, arrangeable on tour with your leader while in Santorini.

Unwind on Kamari’s black-sand beach, a volcanic shoreline backed by Mesa Vouno and lined with cafés and tavernas. Swim in clear water, stroll the promenade, or simply recline on a sunbed as the Aegean sparkles.

Smooth pebbles, pumice cliffs and surf create a striking coastal setting for relaxation between hikes. This is an optional experience at additional cost, bookable locally on tour with your leader.

Meet your tour leader and fellow travellers in the Aegean port of Rafina for a relaxed orientation and convivial start. Settle into a harbourside taverna to share a Greek taverna dinner of meze, grilled catch of the day and island salads, with the scent of oregano and sea air setting the tone for your island week.

Hear practical tips for island walking, ferry etiquette and village customs as the lights of fishing boats shimmer across the bay. Raise a glass with toasts with local wines or tsipouro, and feel the week’s rhythm begin as conversation flows and plans take shape.

Simple buffet-style Greek breakfast consists of bread/toast, butter, jam, fresh juice, milk, local yoghurt, eggs and honey, and coffee/tea. In Santorini, it is a basket breakfast in the room. For lunch and dinner, we normally go to different tavernas and restaurants (at times, picnics of locally sourced food will be suggested for lunch instead), where we can sample some typical Greek meze dishes, olives, fresh fish, vegetables and much more.

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