TOLL FREE: 1-800-225-1589
*The red tour trail on the map does not represent the actual travel path.


Hiking the Greek Isles
This magnificent adventure describes a leisurely route across the beautiful landscapes of Greece's Cycladic island group. Our mainland jump-off point is none other than Athens, one of the world's greatest capital cities and a bustling metropolis that fuses antiquity and modernity to spectacular effect.

Then it's on to Santorini and our first hike along the crater rim to a spectacular sunset in Oia. On Amorgos, we tread ancient, cobblestone donkey routes past Byzantine monasteries and olive groves, while on Naxos, we follow the 'Four Villages Route', a walk through beautiful, undulating countryside and some of the prettiest villages in the islands.

And of course a visit to the isles would not be complete without a taste of glam Mykonos, famous the world over as a first class, gay-friendly destination.
16 Sep 2023 - 29 Sep 2023
3580 USD
04 May 2024 - 17 May 2024
3580 USD
31 Aug 2024 - 13 Sep 2024
3580 USD
Day 1 • Arrival in Athens
Welcome to Greece!

Today we arrive in Athens, off-and-on the capital of Greece in its many incarnations over several thousand years. The city received a major facelift for the 2004 Olympics and is looking better than ever, with buildings and monuments cleaned and renovated, and newly created pedestrian areas near the Ancient Agora and Acropolis.

Overnight in Athens.
Meal plan: Dinner
Day 2 • Athens: City Tour
The best way to explore a city is on foot, and this is especially true of Athens, which has a number of sites located in close proximity to each other. From our hotel we will enter Plaka, the old town of Athens. Standing on a small square is the Lysicrates Monument, a cyclical tower from the 4th century BC. From here, it is just a brief walk along Dionysiou Areopagitou Street to the southern slope of the Acropolis.

The highlight of this tour is the ascent to the Acropolis with its architectural masterpieces dating back to the 5th century BC. We reach the top of this hill by entering through the monumental Propylea in order to admire the magnificent Parthenon and the graceful Caryatid statues at the Erechthion Temple.

Turning right at the exit of the Acropolis, we will come to Arios Pagos -- a small hill or a large rock, depending on how you look at it -- which was used as the seat of court during the 5th century BC. This is the place were the Apostle Paul preached to the citizens of Athens 2,000 years ago. The stairs next to the Arios Pagos take us down to the Ancient Agora marketplace. Among the numerous sights in this archaeological park is the well-preserved Temple of Hephaistos
and the reconstructed Stoa Attalou. A short stroll away is the more recent Roman Agora from the first century BC and the landmark Tower of the Winds.

At Areos Street, just before Monastiraki Square, are the remains of Hadrian's Library -- a Roman building from the 2nd century BC. A ten-minute walk along Ermou Street will take us to Keramikos, the final destination on our walking tour. This is the site of the city's ancient cemetery with its beautifully decorated tombstones and splendid collection of pottery inside the small museum.

The balance of the day is yours to explore independently.

Overnight in Athens.
Meal plan: Breakfast
Day 3 • Athens - Fly to Santorini
Today we fly to the island of Santorini, also known as Thira.

Vast geological upheavals have given this island its unique form resulting in the nickname, "Pre-Historic Pompeii." The effect of terracing makes this unlike any other island, Greece's most visually stunning. Santorini is also the island of churches, wine, and donkeys! From as early as 3000 BC the island developed as an outpost of Minoan civilization until around 1500 BC when the volcano erupted. At this point the island's history became linked with the legend of Atlantis.

We generally aim for a morning flight, which will allow us time to drop our bags (check-in later this afternoon - so be prepared!) and take a little orientation stroll around the main town of Fira, enjoying the incredible views.

Fira is the capital of the island and the most important village. Early in the 19th century the capital of the island was moved from Pyrgos to Fira. After the earthquake of 1956 a part of the town was destroyed (only a small part of the 18th century buildings were saved). Fira is perched on the edge of an impressive cliff 260m high and offers a great panorama over the submerged volcano. Here the small streets are filled with all kinds of shops, cafes, and restaurants.

Time-permitting we can break for lunch (on your own account), after which your Tour Leader can recommend some additional sightseeing and/or a hike.

Overnight on Santorini (Fira).
Meal plan: Breakfast and Dinner
Day 4 • Santorini: Akrotiri & the Caldera Rim to Oia
We begin with a visit to Akrotiri, where excavations have revealed a complete prehistoric Minoan city with squares, streets and two-storey houses which contained marvelous frescoes. The buildings date to the late 16th century BC. No skeletons or treasures have been found in Akrotiri, so historians think that the inhabitants were forewarned of the eruption and were able to escape. The excavations have yielded evidence what has revolutionized our knowledge of the Late Bronze Age; indeed the town has been called a "bronze-age Pompeii."

We then travel to Fira where we begin our hike. Today's 3.5 hour hike takes us through the town's narrow walkways northward through the sister villages of Fira -- Firostefani and Imerovigli -- along the caldera rim to Oia ("Ee-ah") via a truly magnificent route. This is the most obvious hike on Santorini and offers many changing views of the deep blue sea, distant snow-white villages, and multi-hued caldera cliffs. Built on a steep slope of the caldera, many of Oia's dwellings nestle in the niches hewn in the volcanic rock. It was once a major fishing port but is principally known these days as probably the most dramatically situated town in the whole of Greece.

This afternoon is yours to explore Oia or Fira on your own. During your time in Fira we recommend a visit to the impressive Archaeological Museum. This museum features many pieces and exhibits specific to the Santorini site of Akrotiri, as well as artifacts dating back to the time of the Cycladic Civilization.

Overnight on Santorini (Fira).
Meal plan: Breakfast and Dinner
Day 5 • Santorini - Ferry to Amorgos
Today we travel by ferry to the isle of Amorgos. The ferry likely stops at several lesser islands along the way and drops us at either Katapola, the main port of Amorgos, or Aegiali, the island's secondary port. If we must disembark at Katapola, we will travel by road to Aegiali where our hotel is located. We will likely arrive in time for dinner.

Amorgos's timeless monastery, scattered churches, and pleasant beaches offer both respite from tourists on the other islands and a taste of traditional Greece. For many, Amorgos has become the highlight of the tour, accurately described as "the soul of Greece." The locals are extremely friendly, the mountains surrounding the port majestic, and the sunsets stunning. It has been the location of several movies and is a super place for walks through idyllic olive groves. After bustling Santorini, this will be an abrupt shift of gears from touristic Greece to a much mellower and more authentic version.

Overnight on Amorgos.
Meal plan: Breakfast and Dinner
Day 6 • Amorgos: Tholaria & Langada
This hike is one of the most beautiful on Amorgos. The whole route involves magnificent ancient trails through the paleis above Aegiali. The panoramic views and the villages make this day an unforgettable experience. Aegiali is an area consisting of three traditional villages: Langada, Tholaria, and Potamos, which climbs the slope of the highest mountain on Amorgos, Krikellos (821m 2709 ft). They are built above a deep valley and the harbour of Aegiali where a beautiful sandy beach spans the gentle curve of the bay.

We begin our walk at Tholaria, located close to the location of the ancient city of Aegiali (Vigla). Our path is a cobbled donkey route that connected the villages prior to the building of the road (though locals still make the journey by donkey). This first stretch is a traverse that affords spectacular views of the entire valley and its three villages. We come to the gorge of Araklos, the historical church of Agia Triada, the old church of Panagia Epanohoriani, and the half-ruined settlement of Stroumbos.

Langada is located at the end of the valley in an idyllic location among steep rocky peaks and deep valleys. One hour from Langada (for those with energy remaining!) we can see the unique Byzantine monument of Theologos, a monastery of early Byzantine years. A bit further, the historical little chapel of Stavros is situated.

Langada is a great place for lunch. From here you can take the local bus back down to the harbour area, or stroll the downhill stretch through olive groves. The truly energetic can continue their hike another hour or up a steep path to a row of centuries old ruined windmills at an altitude of 540m / 1,792 ft. This makes for an exceptional spectacle; you stand on a rather narrow rocky ridge and you have an overview over the entire island, with the sea on both sides. All around you can see different islands: towards the south-east Astipalea, Anafi and Santorini, towards the north Ios, the small Cycladics, Naxos, Donoussa and even, on a clear day, Ikaria, all the way in the north-east. There is usually a lot of wind here, even when there is no wind at all down in the valley. The multitude of walls and fields at your feet make you dream about past agriculture and about all the activities that once took place up here.

DAY SUMMARY: The hike takes a little over four hours (real walking time). Terrain is undulating with loose stones and cobbled surfaces.

Overnight on Amorgos.
Meal plan: Breakfast and Dinner
Day 7 • Amorgos: Chora & Chozoviotissa Monastery (to Aegiali)
Early this morning we travel by road to Chora, the capital of the island. We will pause here to stroll about the village, set high above the sea protected from pirates of bygone days. We leave the village and follow a magnificent staircase going down to the Monastery of Chozoviotissa. The dazzling white building, founded in the year AD 1099, clings precariously to a cliff face. We will enter the monastery and climb into its snug interior. Hopefully the docent will be available to show us around and provide access to the tiny but fascinating museum.

After our visit to the monastery, we commence our hike.* This is definitely one of the most fabulous hikes in the Cyclades, and the longest and most difficult of our trip. We follow the spine of the island and discover some unique landscapes and flora and, of course, some stupendous views. Leaving the monastery, we climb a staircase into an impressive landscape; the silence is overwhelming. High above us towers a huge cliff and on the right you see the deep blue sea below.

We continue through impressive and rocky wilderness; soon we reach a kind of saddle with the two coasts of Amorgos both before and behind us. Soon we come to the Xenodochio, the remnants of a kind of medieval hotel on the roadfrom Chora to Aegiali. Gradually we get a great view on the elongated offshore islet of Nikouria. At Exo Meria, situated on a rocky plateau, we find some deserted houses and the ruins of two windmills. It is hard to imagine how difficult and lonely life must have been on this desolate spot.

The trail now continues like a magnificent balcony: far away you can already distinguish the village of Tholaria and all of a sudden you get a great view on the bay of Aegiali where our hike ends at a lovely beach where you can cool off and relax until dinner.

DAY SUMMARY: Approx 4-5 hours (actual walking, longer with stops) on uneven, undulating terrain. The path is quite well worn at first, though in places the route becomes quite vague. Expect loose stones and gravel. There is no shade along the route and one can expect a chill wind, especially in the spring (thought the stupendous wildflowers make up for this!).

* Some travellers choose to visit Chora and the monastery ONLY and forego today's hike. Please confer with your Tour Leader who, by this point, will have a good sense of your suitability for today's plans. A free afternoon on a beautiful island is often welcomed by tour participants.

Overnight on Amorgos.
Meal plan: Breakfast and Dinner
Day 8 • Amorgos - Ferry to Naxos
Today we travel by ferry to the island of Naxos, the largest of the Cyclades Islands. Green, fertile, largely self-sufficient Naxos has not needed to go all out to attract tourists. This wealthy agricultural island exports an abundant harvest of olives, grapes, and potatoes throughout the Aegean, and only recently has begun to cater to tourists.

On arrival we will have a walking tour of Naxos Chora, the main town and capital of the island. On our stroll you will note the architecture of Naxos, distinct from that of any other Cycladic isle. The Venetians ruled this island from 1207 until the island fell to the Turks in 1566. Some descendants of the Venetians still live here and the influence of Venetian architecture is obvious in the Kastro and the fortified Venetian towers. Also specific to Naxos is the remarkable abundance of small Byzantine chapels, many of which contain exceptional frescoes dating from the 9th to the 13th centuries.

Our walk ends at the Portara, the big marble gate that stands high on the island of "Bacchus" and is the remains of the ancient temple of Apollo. The ruins of the temple are called "Palace" implying the palaces of Ligdami the ancient tyrant of Naxos (6th century BC). The legend says that Theseus abandoned Ariadne there when he passed through Naxos after he slew the mythical minotaur on Crete.

While in town you should purchase picnic items for tomorrow's hike, though we should be able to acquire refreshments in the villages we visit.

Overnight on Naxos.
Meal plan: Breakfast
Day 9 • Naxos: Apiranthos - Fanari - Chalki
This is the ideal hike on Naxos that ties together some of the prettiest villages on the island along an obvious, undulating route marked by red dots.

We start in the picturesque village of Apiranthos where we can first wander around for a short spell. We can visit the folk museum, consisting of three rooms of a not too old house: in the living room, the kitchen and the bedroom you can see all kinds of traditional objects and tools.

For the start of the actual hike, we leave from this beautiful little square and pass the church Kimissis tis Theotokou and church of Agia Paraskevi, with its white dome. We enjoy a wonderful descent on a meandering rocky trail amidst an impressive landscape. On the right you see the steep cliff of the Fanari, in front of you there is the marvellous valley with the villages of Moni, our next village.

At this point the path bends to the left sharply whereupon the really beautiful trail zigzags further upwards. The retaining walls of the monopati are still clearly visible. The path goes up fairly steeply and behind you, you can see that Apíranthos is quite extensive -- it also appears to consist of two parts. Beyond the village, towards the south east, you have a great view on the island of Donoussa, the island of Amorgos and behind the hill the other small islands.

We now walk again on a marvellous stone path and we can imagine ourselves on a green slope in the Alps. This is a truly beautiful climb; during the final minutes you take a meandering staircase, which has been crumbled away by unknown forces. On the right, on the lowest summit of Fanari, we find the small church with a picnic table. We have a great panoramic view: in the Tragea Valley you can see the villages of Damarionas, Chalki, and Moni. Beyond you can discern the bay of Naxos, with also the islands of Paros, Syros, Tinos and Mykonos.

We return to Apiranthos for lunch, and then take the local bus to Chalki where we can visit a distillery and walk to a Byzantine church. We return to our hotel in the late afternoon.

DAY SUMMARY: Altogether we have about three hours of actual hiking time, which means that in reality we should devote about six hours to this hike. We regret that the trail is somewhat overgrown and unmaintained in spots, but the route is still very rewarding.

Overnight on Naxos.
Meal plan: Breakfast and Dinner
Day 10 • Naxos - Ferry to Mykonos
This morning we travel by ferry the short distance to the island of Mykonos and transfer to our hotel located a short drive away from town at Platy Yialos beach, where we can enjoy the peace and quiet away from town but still be close enough to conveniently access Chora using the frequent local buses.

Later this afternoon we venture into town for a walking orientation tour before dinner in town. We wander the pirate-proof streets of town and see the Paraportiani Church near the quay, an architectural masterpiece of five chapels in one. From the harbour waterfront, you can watch the local fishing boats, or venture into the labyrinth of dazzling, white-washed streets to the many churches, tavernas, or shops selling artisan crafts, jewelry and the latest fashions. In the distance stand a string of windmills that once harnessed the breezes of days gone by. As one of the most cosmopolitan Greek islands, Mykonos is legendary for its shopping and nightlife.

After our walk we will have dinner at one of the many restaurants in town before sampling some of the gay nightlife. Bus or taxi back to our hotel on your own.

Overnight on Mykonos.
Meal plan: Breakfast and Dinner
Day 11 • Mykonos: Free Day
There are many beaches on Mykonos and today we can enjoy them to their fullest. You can also head back into town for more independent exploration and/or shopping. Your Tour Leader can help you plan your day. Enjoy!

Overnight on Mykonos.
Meal plan: Breakfast
Day 12 • Mykonos: Boat trip to Delos
This morning (not toooo early) we meet the boat and guide who will take us to the tiny sacred island of Delos (30 minutes away).

Delos gives the whole group of islands surrounding it their name, the Cyclades -- so named because they form a circle (kyklos) around Delos. We will see the Agora of the Competialists, Roman merchants or freed slaves who worshipped the guardian spirits of crossroads; the Sanctuary of Apollo, the three temples of Apollo and the Sanctuary of Dionysus. In the House of the Masks we are able to see a mosaic portraying Dionysus riding on a panthers back. The theatre here could seat 5,500 people. From the top of Delos Mountain we have a spectacular view of the entire island.

We return to Mykonos with the balance of the day at leisure (you may also return to Mykonos at your leisure spending as much time as you like on Delos). This evening we reconvene for our last island dinner. Hopefully during one of our evenings on the island, we'll be able to enjoy some of the island's nightlife, such as a cabaret or drag show. As such things come and go without warning, however, it's hard to promise well in advance. Your Tour Leader will have his/her ear to the ground as our visit approaches.

Overnight on Mykonos.
Meal plan: Breakfast and Dinner
Day 13 • Mykonos - Ferry to Athens
Today we take the fast ferry back to Athens.

Time-permitting back in Athens, we recommend a visit to the Museum of Cycladic Art, devoted to the study and promotion of ancient Greek art. The main exhibit, the Cycladic Collection, contains 350 objects representative of every phase or type of artifact that Cycladic islanders have left us, be that marble sculpture, pottery, or metal ware. You should also have some time for some last-minute shopping in the Plaka distict before our farewell dinner.

* Some past travellers have elected to extend their stay on Mykonos and not return to Athens today. Please let us know well in advance if this option is of interest to you.

Overnight in Athens.
Meal plan: Breakfast and Dinner
Day 14 • Departure from Athens
Departure from Athens.

Meal plan: Breakfast

For detailed itinerary (PDF), click here
  • Breakfast daily and most dinners (hotels & local restaurants)
  • All accommodation, transport, sightseeing and entrance fees for sites noted as 'visited' in the detailed itinerary
  • Gratuities for restaurant staff, porters (if available)
  • Airport transfers for land & air customers arriving / departing on tour dates
  • Tour Leader gratuities, lunches, some dinners, drinks, personal items (phone, laundry, etc), international air taxes (if applicable), any excursions referenced as 'optional'
  • Airport transfers for Land Only customers
  • Optional trip cancellation insurance and single supplements fees
  • Our post-reservation trip notes offer further guidance on optional meal costs and shopping
Though still a traditional and relatively devoutly religious country, Greece is one of the more tolerant societies in the Western world. Gay culture, though not as organized and obvious (ie ghettoized) as in other European countries, is met with tolerance, or at least indifference, by the vast majority of the population.

As long as you are respectful of local sensitivities, ie discrete, the locals will be almost invariably charming and welcoming. Of course, in places like Mykonos and, increasingly, Santorini, practically anything goes.
This itinerary is correct at time of publishing. For a more detailed itinerary, download a PDF here. We reserve the right to make changes as necessary due to reasons beyond our control. For booking terms and conditions, please refer to our Booking Terms.
click here toBOOK NOW
Group size
Maximum 16 plus Tour Leader
Staff & Support
Tour Leader and local guides at various locations.
Well-located, air-conditioned, mid-range hotels (3-star) throughout. Island hotels are smaller properties (3-4 story) that will likely not have elevators. All hotels have en suite bath, though most have shower only. A special note about Santorini, which is primarily a luxury tourism destination and, while we can confidently promise our visit will be fulfilling and rewarding, one's hotel expectations must be in line with our overall purpose, which is sightseeing and cultural experience and not focused on the "hotel experience" per se.

Porter service is rarely available on the islands (see 'inclusions'); you MUST be independent with your luggage, especially getting on / off ferries. Single rooms are limited and likely smaller than twins. Many hotels have swimming pools and / or beach access.
For hotel samples, click here
Transport & travel conditions
Local ferries between mainland/islands can range from hydrofoils to large vehicular vessels--all bookings in economy class. Greek ferry schedules tend to change without notice; some itinerary adjustments may be necessary at the discretion of your Tour Leader.

Land transport (island touring, port transfers) by private bus, public bus, and taxi.

Because some hikes can/may be adjusted at the discretion of your Tour Leader depending on things like weather and group interest, the final distances/durations of our hikes as indicated in our itinerary should be taken as guidance only. In the meantime, however, we can advise that, generally-speaking, our walks are leisurely on well-trodden pathways over undulating terrain (some walks are downhill), 2-5 hours in overall duration with plenty of breaks for refreshment, photos, and taking it all in. Please note that some surfaces feature loose material (ie stones, gravel, sand etc) which can be slippery. Good footwear/tread and walking poles will help to steady you and support your knees.

While our "level 3" difficulty rating refers to the walks/hikes that are spread throughout our program and, while this activity does not occur every day, even when not on a "hike," we will be on foot quite a lot with town walking tours, site visits, and plenty of places with uneven surfaces and stairs. Participants should be fit and active and accustomed to trail walking, possibly in some remote locations, and be prepared to engage in a conditioning regimen prior to the trip.

This is a hotel-based tour with no camping, and you are required to only carry what you need for the day.

For daily summary of our hiking activities, please refer to the tour itinerary.
This tour is offered in spring, summer and fall, the most popular of which are spring and fall when temperatures are relatively mild. Spring is popular for green landscapes and wildflowers; fall is popular for warm seas and locally harvested produce. Those who enjoy busy beaches and the most active nightlife prefer summer, though heat is a factor on our walks. Showers are possible in spring but unlikely in summer and fall.