Cornelius Amann
October 06, 2026
5/5
Greek Islands on Foot: Naxos, Amorgos and Santorini
8 days from Athens: three nights on Naxos for Mount Zas and the Tragaea villages, two on Amorgos for Hozoviotissa, then the Santorini caldera walk and a flight back to Athens.
8 days · Round trip from Athens · up to 12 guests
Hozoviotissa monastery on the cliffs of Amorgos Photo: Apenauta at Italian Wikipedia, Public domain, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Hozoviotissa_2012_a.JPG)
The facts
At a glance
- Length
- 8 days, 7 nights
- Start and end
- Round trip from Athens
- Group size
- 7 to 12 guests
- Longest drive
- 1.5 h on day 4No drive day is longer than 4 hours.
- Activity level
Moderate
Walks of 2 to 4 hours on five days, on old stone mule paths, village steps and open hillside, plus short town walks on the other days. The hardest is Mount Zas on day 4: about 6 to 7 km return with 500 to 600 m of climb on loose rock and almost no shade, to about 1,000 m. The Santorini caldera walk on day 8 is about 10 km and 3 to 4 hours. Every long walk has a shorter version with the van covering part of the way, and you can sit out any walk.
- Meals included
- 7 breakfasts, 5 lunches, 2 dinners
- Room of your own
- + CAD 795 (estimated price)
- Season
- May to June and September to October
Highlights
Why this trip
- Sunset at the Portara on Naxos, the marble gateway of an unfinished temple to Apollo
- Old mule paths through the olive groves of the Tragaea from Halki to Filoti
- The summit of Mount Zas, about 1,000 m and the highest point in the Cyclades
- Cooking island dishes with a Naxos family, then eating them at their table
- Hozoviotissa, the white monastery built into a cliff 300 m above the sea on Amorgos
- The mountainside path from Langada to Tholaria above the bay of Aegiali
- Sailing into the Santorini caldera and sunset from Imerovigli, away from the Oia crowds
- The caldera walk from Fira to Oia from 7 am, before the day's visitors
What makes this trip different
Short drives, all published
Every drive is listed day by day, and none is longer than 4 hours.
Free time is part of the plan
Free time and choices are marked on the days they fall.
Solo without the penalty
A room of your own is + CAD 795 (estimated price).
Day by day
Itinerary
The longest drive is 1.5 h, on day 4.
Tap any stop on the map to open that dayClick any stop on the map to open that day
Arrive in Athens
Athens International Airport to your hotel in central Athens, then Plaka on foot
- Welcome dinner
- Stay in Athens
- Drive about 45 min
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.
Evening
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
Ferry to Naxos, sunset at the Portara
Athens to Piraeus, ferry to Naxos, then Naxos Chora on foot
- Breakfast
- Stay in Naxos
- Drive about 30 min
Morning
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.
Afternoon
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.
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
- Breakfast, lunch and dinner
- Stay in Naxos
- Drive about 1.5 h
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.
Afternoon
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.
Evening
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.
Naxos: Mount Zas and Apeiranthos
Naxos Chora to the Aria spring above Filoti, Mount Zas on foot, then Apeiranthos
- Breakfast and lunch
- Stay in Naxos
- Drive about 1.5 h
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.
Morning
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.
Afternoon
We come down for a late lunch in Apeiranthos, a mountain village built and paved in white marble, with arched lanes and small museums.
Evening
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.
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
- Breakfast and lunch
- Stay in Amorgos (Chora)
- Drive about 30 min
Morning
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.
Afternoon
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.
Evening
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.
Amorgos: Hozoviotissa and the Langada to Tholaria path
Amorgos Chora to Hozoviotissa monastery on foot, then Langada to Tholaria and Aegiali
- Breakfast and lunch
- Stay in Amorgos (Chora)
- Drive about 1.5 h
Morning
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.
Afternoon
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.
Ferry to Santorini and the rim to Imerovigli
Katapola to Santorini (Athinios) by ferry, then Fira and the caldera rim to Imerovigli
- Breakfast and dinner
- Stay in Santorini (Fira)
- Drive about 30 min
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.
Evening
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.
The caldera walk to Oia, then fly to Athens
Fira to Imerovigli, Skaros and Oia on foot, then Santorini airport (JTR) to Athens (ATH)
- Breakfast and lunch
- Drive about 45 min
Morning
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.
Afternoon
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.
Evening
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.
- Athens1 night
- Naxos3 nights
- Amorgos (Chora)2 nights
- Santorini (Fira)1 night
- Athensend
- Overnight stop
- Day trip
- By boat or train
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.
Want this plan in your inbox?
Get the day-by-day itinerary by email, or ask us anything about this trip. A trip planner replies the same or next business day.
Before you book
Right for you?
Good for you if you want
- Walkers who want the Cyclades on foot, with a ferry between islands rather than a coach
- Travellers curious about Amorgos and inland Naxos rather than beach clubs
- Solo travellers who want one steady group and a guide on every island
- People who like an easier version on hard days and a free afternoon after a walk
Not for you if you want
- Step-free access: island towns, paths and the monastery are steps and uneven stone
- A beach or party-island holiday
- A summer trip: we run in spring and autumn only
- Travellers who want several nights on Santorini (see our Athens, Naxos and Santorini trip)
Book flights after we confirm your seat.
7 nights
Where you'll stay
Your hotels are named in your trip confirmation.
- Athens1 night
- Naxos3 nights
- Amorgos (Chora)2 nights
- Santorini (Fira)1 night
One price
What's in the price
Included
Accommodation
- 7 nights in central hotels of at least a 3-star-plus standard: 1 in Athens within walking distance of Plaka, 3 in Naxos Chora, 2 in or near Chora on Amorgos, 1 in or near Fira on Santorini
- Rooms shared, or your own for a supplement
- We name each hotel when we confirm your dates
Transport
- Pick-up at Athens International Airport (ATH)
- Ferry tickets Piraeus to Naxos, Naxos to Amorgos and Amorgos to Santorini, with luggage handled
- Flight from Santorini (JTR) to Athens (ATH) on the last day, with a checked bag
- A local van and driver on each island for transfers and to shadow the walks
Your guide
- A See Sight Tours guide with the group for the whole trip, on every ferry and every walk
- Licensed local guides where a site requires one
Activities
- Athens: evening walk through Plaka
- Naxos: the Kastro and the Portara, the Tragaea path from Halki via Panagia Drosiani to Filoti, the kitron distillery in Halki, Mount Zas and the Zas cave, Apeiranthos, a Cycladic cooking evening with a local family
- Amorgos: the old path from Katapola past ancient Minoa to Chora, Hozoviotissa monastery, the Langada to Tholaria path
- Santorini: the rim walk from Fira to Imerovigli at sunset, the caldera walk from Fira to Oia
Meals
- Breakfast daily (7)
- 5 lunches: the Tragaea, Apeiranthos, Katapola, Tholaria and Oia
- 3 dinners: welcome dinner in Athens, the Naxos cooking evening and a farewell dinner on Santorini
Not included
- International flights to Athens and home
- A night in Athens after the trip
- Travel insurance
- The ETIAS travel authorisation fee, if it applies to you
- Meals not listed, including lunch on the ferry days to Naxos and Santorini
- Drinks, except at the welcome dinner, the cooking evening and the farewell dinner
- Sunbeds and umbrellas on beaches
- Tips
- Optional activities you add yourself, such as a caldera boat trip or the Fira cable car
- Personal expenses
Extras
- Room of your own
- CAD 795 (estimated price)
When you can go
Dates and prices
Pick your start date when you request to book. We check that date and confirm it in your quote.
Prefer to travel without a group or guide? Ask us about arranging hotels, transport and city tours for you to travel independently.
Before you book
Booking terms
Nothing is charged now. Full terms and the cancellation schedule come with your quote, before you accept.
Business addresses
See Sight Tours Trips (USA): 3172 N Rainbow Blvd, Las Vegas, NV 89108, United StatesSee Sight Tours Trips (Canada): 5305 50 Avenue, #1091, Red Deer, AB T4N 4B6, Canada+1-888-961-6584Guest reviews
What guests say
Reviews from guests on our day tours.
Jane
October 06, 2026
5/5
Susan
October 06, 2026
5/5
Tom L
October 05, 2026
5/5
MandL83
October 05, 2026
5/5
Darren O
October 05, 2026
5/5
Good to know
Questions
What does the price include?
Seven nights in central hotels, breakfast daily, five lunches, the welcome dinner, the Naxos cooking evening and a farewell dinner, all three ferries with luggage handled, the flight from Santorini to Athens with a checked bag, every transfer, your See Sight Tours guide throughout and every walk and visit in the day plan, including Hozoviotissa.
Is it cheaper to book the islands myself?
A little, for the bare bones. Booked yourself in spring or autumn, the hotels, three ferries and the flight cost roughly CAD 1,100 to 1,900 per person sharing; the 15 included meals add about CAD 500 to 700, and taxis and transfers about CAD 300 to 500. The rest is the guide on every walk and ferry, the van shadowing the walks, and someone rebooking when a ferry is cancelled.
How hard is the walking?
Moderate. Five days have walks of 2 to 4 hours, mostly on old stone paths and steps; the hardest is Mount Zas on day 4, about 6 to 7 km with 500 to 600 m of climb. Every long walk has an easier version where you ride part of the way, and nobody is left behind.
How big is the group?
The small-group trip runs with 7 to 12 guests, the same people from Athens to Santorini. That keeps ferry boarding quick, fits the group around one taverna table and means everyone can hear the guide on narrow island paths.
Who leads the trip, and does the guide come on the ferries?
A See Sight Tours guide travels with the group for the whole trip, on all three ferries and every island day, and handles tickets, luggage and changes. On the islands we use local vans and drivers, and where a site needs a licensed local guide, one joins us.
I'm travelling solo. Is there a single supplement?
Rooms are priced for two sharing. A room of your own is from CAD 795 extra, shown before you book. Solo guests do every walk and every group meal with the group, with no difference in the plan. Ask us about sharing a room with another solo guest of the same sex.
When is the best time for walking in the Greek islands?
May, June, September and October. The paths are warm but walkable, spring brings wildflowers and autumn a warm sea. We do not run this trip in July and August: Mount Zas and the Amorgos paths have almost no shade, and the meltemi wind is at its strongest.
What happens if a ferry is cancelled?
Your guide watches the forecast and the port notices, moves us to another sailing or route, usually via Naxos, and rearranges the walks so the island days still happen. Strong wind can stop smaller boats, which is why Santorini's walk is on the last morning.
Is there a dress code at Hozoviotissa monastery?
Yes. The monastery asks for long trousers or a long skirt and covered shoulders; shorts and bare shoulders are turned away. Carry a light pair of trousers or a wrap skirt and a scarf in your day bag on day 6. It opens in the morning and late afternoon and closes in the middle of the day.
Do I need a visa for Greece?
Canadian and US passport holders do not need a visa for stays of up to 90 days in the Schengen area, which includes Greece. The EU's entry system records your passport at the border. ETIAS, the EU's travel authorisation, has been announced but its start date keeps moving; we tell you at booking whether it applies.
How does booking work?
You send a request to book with your preferred departure and room type. We confirm availability, the hotels and the final price within 24 hours. No payment is taken with the request; we send terms and a deposit request only once your place is confirmed.
Can I do this trip on my own dates?
Yes, as a private trip for your party on a date you choose, with your own guide, at the private price. If you want to walk the islands on your own without a guide, ask us for an independent quote with hotels, ferries and route notes; that is an inquiry, not a style of this trip.
See Sight Tours has been providing travel services across North America since 2006. Operating in 20 cities across Canada and the USA, the company specializes in small group tours that offer personalized, high-quality experiences for travelers.
Book your Tour
Get in Touch
- Toll Free1-888-961-6584
- Local1-289-271-9767
© 2026 See Sight Tours. All rights reserved.