Greek Islands on Foot: Naxos, Amorgos and Santorini

1. Day 1: Arrive in Athens

   Athens International Airport to your hotel in central Athens, then Plaka on foot

   • Drive about 45 min
   • Welcome dinner
   • Stay in Athens
   Day 1 details

   Fly into Athens International Airport (ATH), about 35 km east of the centre, where a driver meets you in arrivals for the drive to a central hotel within walking distance of Plaka. To join the evening walk and dinner, plan to land by about 3 pm; the meeting time comes with your final itinerary. In the early evening your See Sight Tours guide meets the group for a short briefing on the week: the three ferries and how we handle the luggage, the walking on each island and the easy and harder versions of each walk, and why we keep the Santorini caldera path for an early start on the last morning. Then we walk together through the Ancient Agora side of Plaka and up the lanes under the north slope of the Acropolis as the lights come on, a first look at the rock before the islands. Dinner is a welcome meal at a taverna in the neighbourhood: mezze, grilled fish or meat and a first glass of Greek wine. Athens has one night only on this trip; we can add nights before the start if you want the Acropolis and its museum.

   Included

   • Pick-up at Athens International Airport (ATH)
   • Welcome briefing with your guide
   • Evening walk through Plaka below the Acropolis
   • Welcome dinner in Plaka

   Free time: Free until the evening briefing

   

2. Day 2: Ferry to Naxos, sunset at the Portara

   Athens to Piraeus, ferry to Naxos, then Naxos Chora on foot

   • Drive about 30 min
   • Breakfast
   • Stay in Naxos
   Day 2 details

   After an early breakfast we drive about half an hour to the port of Piraeus for a morning ferry to Naxos. Depending on the boat the crossing takes about four to six hours, usually calling at Paros; we buy the seats and move the luggage, and you can sit out on deck as the Cyclades come up. We pick a sailing that does not need a pickup before first light. Lunch is your own, on board or at the harbour when we land. Naxos is the largest of the Cyclades and the most mountainous, and we stay three nights in Chora, the main town, near the harbour, so you unpack once. After time to settle in, your guide leads a short walk up through the stepped lanes of the Kastro, the hilltop quarter built after the Venetian Marco Sanudo made Naxos the seat of his Duchy of the Archipelago in 1207, and back down along the causeway to the Portara, the marble gateway of a temple to Apollo left unfinished in the 6th century BC. It faces west, and the town comes here to watch the sun go down.

   Included

   • Transfer to Piraeus and ferry tickets to Naxos, with luggage handled
   • Walk through the Kastro, the Venetian old town of Naxos Chora
   • The Portara at sunset

   Easier option: Skip the Kastro steps and meet the group at the Portara causeway, which is flat, for sunset.

   More active option: Before the walk, swim at Agios Georgios, the town beach about 10 minutes on foot from the harbour.

   Free time: Evening free for dinner in Chora

   Activity: About 1 hour on foot, with steps in the Kastro; the Portara causeway is flat.

   

3. Day 3: Naxos: the Tragaea villages path and a cooking evening

   Naxos Chora to Halki, on foot through the Tragaea to Moni and Filoti, then a village kitchen

   • Drive about 1.5 h
   • Breakfast, lunch and dinner
   • Stay in Naxos
   Day 3 details

   Today goes inland, to the high green valley of the Tragaea in the middle of the island, about 25 minutes by van. We start walking in Halki, once the island's inland capital, where the Vallindras distillery has made kitron, a liqueur from citron leaves, for over a century; we look in at the old copper stills. The path then leaves the village on old stone mule tracks between walls and olive groves, past small Byzantine chapels, to the church of Panagia Drosiani near Moni, one of the oldest on the island, with early frescoes inside. Lunch is a sit-down meal in a village taverna. In the afternoon the walk continues to Filoti, below the slopes of Mount Zas, where the van waits. In all it is about 9 km and 3 to 4 hours on foot with gentle climbs, and the van can collect anyone at Moni. After a free late afternoon in Chora, the evening is a Cycladic cooking class with a local family: we make a few island dishes with their cheese, vegetables and herbs, then sit down together to eat them.

   Included

   • Kitron distillery visit in Halki
   • Guided walk through the Tragaea from Halki via Panagia Drosiani and Moni to Filoti, about 9 km
   • Sit-down lunch in a village taverna
   • Cycladic cooking evening and dinner with a local family

   Easier option: Walk only the first stretch, Halki to Panagia Drosiani and Moni, about 4 km and 1.5 hours, then ride the van to lunch and Filoti.

   More active option: Add the climb from Filoti to the hilltop chapel above the village before the van, about 45 minutes extra.

   Free time: Late afternoon free before the cooking evening

   Activity: Stone tracks and village steps; little shade between villages, so bring water and a hat. Panagia Drosiani is a working church: covered shoulders and knees.

   

4. Day 4: Naxos: Mount Zas and Apeiranthos

   Naxos Chora to the Aria spring above Filoti, Mount Zas on foot, then Apeiranthos

   • Drive about 1.5 h
   • Breakfast and lunch
   • Stay in Naxos
   Day 4 details

   Mount Zas, at about 1,000 m, is the highest point in the Cyclades, and on a clear day the view from the top takes in most of the islands around Naxos. We leave Chora after breakfast and drive about 40 minutes to the Aria spring on the road above Filoti, where the path starts. The way up passes the cave where, in myth, Zeus was raised, then climbs on a rocky, waymarked path through low scrub to the summit: about 6 to 7 km there and back with about 500 to 600 m of climb, 3 to 4 hours with stops, and almost no shade, which is why this is a spring and autumn trip and why we start in the morning. We come down for a late lunch in Apeiranthos, a mountain village built and paved in white marble, with arched lanes and small museums. The van takes us back to Chora by mid-afternoon, and the rest of the day is free: a swim at Agios Georgios, the town beach a short walk from the harbour, or a slow evening in the Kastro.

   Included

   • Guided hike up Mount Zas from the Aria spring, about 6 to 7 km return
   • The Zas cave on the way up
   • Late lunch in Apeiranthos, the marble village
   • Walk through Apeiranthos

   Easier option: Walk only to the Zas cave and back, about 1 hour, or skip the mountain and spend the morning with the van in Filoti and Apeiranthos.

   More active option: Descend the far side of the mountain toward the chapel of Agia Marina and meet the van below, a longer traverse of about 9 km.

   Free time: Afternoon and evening free

   Activity: The hardest day of the trip: steady climbing on loose rock, about 500 to 600 m up and down. Boots or trail shoes with grip, poles if you use them, at least 1.5 litres of water.

   

5. Day 5: Ferry to Amorgos and the old path to Chora

   Naxos to Katapola by ferry, then on foot from Katapola past ancient Minoa to Amorgos Chora

   • Drive about 30 min
   • Breakfast and lunch
   • Stay in Amorgos (Chora)
   Day 5 details

   A late-morning ferry takes us east from Naxos to Amorgos, the long, steep island at the edge of the Cyclades. Depending on the boat and the day, the crossing takes about 1.5 to 4 hours; the slower boats call at the Small Cyclades on the way, a fine way to see them. We land at Katapola, the main port in a deep bay, and have lunch by the water while the van takes the bags up to our hotel in or near Chora, the capital, set on a ridge about 300 m above the sea. In the afternoon light we walk up after them on the old stone path from Katapola, past the hilltop remains of ancient Minoa, a town founded about 3,000 years ago, and up to Chora. It is about 4 km and around 2 hours with a steady climb. Chora is a small white town of lanes, chapels and windmills under a rock topped by a Venetian castle, and in the evening it fills with locals more than visitors. Dinner is free.

   Included

   • Ferry tickets from Naxos to Amorgos, with luggage handled
   • Lunch at Katapola harbour
   • Guided walk on the old path from Katapola past ancient Minoa to Chora, about 4 km

   Easier option: Ride up to Chora with the bags and meet the group for an evening stroll through the town.

   Free time: Evening free in Chora

   Activity: A steady climb of about 300 m on old paving and steps, mostly in the open. If the ferry runs late, we walk Minoa to Chora only.

   

6. Day 6: Amorgos: Hozoviotissa and the Langada to Tholaria path

   Amorgos Chora to Hozoviotissa monastery on foot, then Langada to Tholaria and Aegiali

   • Drive about 1.5 h
   • Breakfast and lunch
   • Stay in Amorgos (Chora)
   Day 6 details

   We walk out of Chora after breakfast on the stepped path down toward the sea and the monastery of Hozoviotissa, founded in the 11th century and built into a sheer cliff about 300 m above the water, white against orange rock. It is about 1.5 km each way with a steep stretch of steps. We aim to be at the door when it opens in the morning, before the day's visitors; inside, the monks usually offer a glass of raki and a loukoumi. The monastery has a strict dress code: long trousers or skirts and covered shoulders, and it closes in the middle of the day. Back in Chora, the van drives about 30 minutes to Langada, a white village high in the north of the island. From here the path runs along the mountainside above the bay of Aegiali, past chapels and terraces, to Tholaria, about 5 km and 2 hours. We have a long, late lunch in Tholaria, then the van takes us back to Chora for a free late afternoon on the hardest day. If you still have legs, walk down about 30 minutes to the beach at Aegiali for a swim instead, and the van collects you later.

   Included

   • Guided walk from Chora to Hozoviotissa monastery and back
   • Visit inside Hozoviotissa monastery
   • Guided walk from Langada to Tholaria, about 5 km
   • Late lunch in Tholaria

   Optional experiences

   • A swim at Aegiali beach, about 30 minutes downhill from Tholaria, with a later van back

   Easier option: Ride the van from Langada to Tholaria and meet the group for lunch; the monastery path can also be shortened by riding to the car park below it, which still leaves a climb of about 300 steps.

   More active option: Walk on from Tholaria to Aegiali by the old path rather than the road, and climb above Langada to the monastery of Theologos before the traverse, about 1.5 hours extra.

   Free time: Late afternoon and evening free

   Activity: About 4 hours on foot in all, with the steepest steps at Hozoviotissa. Bring long trousers or a long skirt and something to cover your shoulders for the monastery.

   

7. Day 7: Ferry to Santorini and the rim to Imerovigli

   Katapola to Santorini (Athinios) by ferry, then Fira and the caldera rim to Imerovigli

   • Drive about 30 min
   • Breakfast and dinner
   • Stay in Santorini (Fira)
   Day 7 details

   We take a ferry south from Katapola to Santorini: about 1 hour 10 to 1 hour 15 on the Seajets fast boat, about 3 hours 15 on the slow boat. Sailings are fewer in spring and autumn, so on some dates we route via Naxos instead, a longer day on the water that we tell you about when we confirm your dates. If that late arrival misses the Imerovigli sunset, we watch it from the rim in Fira, and tomorrow's walk passes through Imerovigli anyway. The arrival is one of the sights of the trip: the boat sails into the caldera under cliffs about 300 m high, banded red, black and white by old eruptions. Our van climbs the switchbacks from Athinios to a hotel in or near Fira for the last night. After a free hour, your guide walks the group north along the paved rim path from Fira through Firostefani to Imerovigli, about 3 km and an hour, as the light softens. We watch the sunset from Imerovigli, where it is far quieter than in Oia, and then sit down to a farewell dinner. Tomorrow starts early, so the evening ends at a sensible hour.

   Included

   • Ferry tickets from Amorgos to Santorini, with luggage handled
   • Transfer from Athinios port
   • Guided rim walk from Fira to Imerovigli at sunset
   • Farewell dinner

   Optional experiences

   • The Fira cable car down to the old port and back, about CAD 15 each way

   Easier option: Ride the van to Imerovigli and meet the group there for sunset.

   More active option: Walk on from Imerovigli toward Skaros rock before sunset, about 30 minutes more there and back.

   Free time: Free time after arrival

   Activity: The rim path is paved with some steps. Lunch is your own on the ferry day because sailing times vary.

   

8. Day 8: The caldera walk to Oia, then fly to Athens

   Fira to Imerovigli, Skaros and Oia on foot, then Santorini airport (JTR) to Athens (ATH)

   • Drive about 45 min
   • Breakfast and lunch
   Day 8 details

   We set off from Fira at about 7 am after an early breakfast, while the air is cool and before the day's visitors come up from the port. The path follows the caldera rim for about 10 km to Oia: through Firostefani and Imerovigli, past Skaros rock, where a Venetian castle once stood, then out along open, unpaved hillside of volcanic soil and pumice with the whole caldera below, small chapels beside the path and Thirasia across the water. Allow 3 to 4 hours with stops; there is one steady climb beyond Imerovigli. We reach Oia in the late morning, while its lanes are still walkable, and sit down to lunch. The van brings us back to the hotel for the bags and on to Santorini airport (JTR) for an afternoon flight to Athens, about 45 minutes in the air and included with a checked bag. Most flights home to North America leave Athens in the morning or around midday, so plan a night in Athens; we can book an airport or city hotel for you.

   Included

   • Guided caldera walk from Fira to Oia, about 10 km
   • Sit-down lunch in Oia
   • Transfer to Santorini airport (JTR)
   • Flight from Santorini to Athens (ATH) with a checked bag

   Easier option: Walk only from Fira to Imerovigli, about 3 km and paved, then ride the van to Oia for lunch.

   More active option: From Oia, walk down the steps to Ammoudi Bay and back up before lunch, about 300 steps each way.

   Activity: About 10 km and 3 to 4 hours with little shade beyond Imerovigli. Book your flight home from Athens for the next day. If you must fly on the same evening, book nothing leaving Athens before about 9 pm, because wind can move our flight. Tell us if you are flying home direct from Santorini.

   

Wildlife and weather: May and June are warm, with wildflowers and herbs on the hillsides, and the sea warms through June. September and October have the warmest sea and settled weather, with shorter days by late October. The meltemi, the north wind of the Aegean, can blow hard in the Cyclades and occasionally stops smaller ferries. We do not run this trip in July and August, when the exposed paths on Zas and Amorgos are too hot by mid-morning.

• Athens1 night
• Naxos3 nights
• Amorgos (Chora)2 nights
• Santorini (Fira)1 night