Donkeys in Santorini Island


Andros.  Mykonos – Delos.  Naxos.  Santorini.

When most people fantasize about Greece, what comes to mind are scenes of stark whitewashed houses against a blinding blue sea. In other words, they envision the Cyclades Islands.  Much of the transcendent effect is due to the Greek light, a light so intense British author Lawrence Durrell likened it to “the naked eyeball of God.”   The walks on this tour hug sea coasts and climb modest mountains, none steep enough to intimidate the moderate walker.  They give you an in depth exposure to these classic islands.


The Cyclades paths take you from village to village along routes that the villagers themselves have used for centuries, primarily with donkeys. You are never far from the sea and almost every summit provides a postcard view of the Aegean and distant islands. Each island is a honeymoon-type haven with romantic sea vistas, windmills, olive groves and ancient ruins.

Andros island is the second largest in the Cyclades but has so few tourists you will feel as if you are hiking on your own private island.   If you think of the Cyclades as dry islands, Andros will change your mind.  For a hiker, it is a relief to encounter so many springs and waterfalls.  Andros also has a diverse variety of trees whose shade is welcome for a hiker.

Glamorous Mykonos is a stark wake-up call that not all Greek islands are quaint and quiet.  Why include it on a low impact hiking tour?  Because Mykonos is the point of departure for tiny Delos island, a one-time sacred sanctuary and World Heritage Site.  It is a wonderful place for walking amidst columns and mosaics and marble statuary.

Naxos is the largest island in the Cyclades and the greenest.  It also has the highest mountains.   There are paths to Za Cave, to 6th century BC kouros statutes left in their quarries, to mountain villages with fresh spring water.   It is also a delight to walk in the Bourgos, the Venetian neighborhood.

Santorini has lots of places to walk and hike, it is hard to narrow down the choices.   The Fira-Oia path on the spine of the island has stupendous views of the caldera and the north side of the island.  A hike that ends at an ancient site is a treat, like Kamari to Ancient Thira.  And you can continue on to Pyrgos, the highest point on the island.

At each island you enjoy fabulous meals at the end of the day.  You will curl up in a very cool and comfortable hotel room because the Cyclades are experts in offering alluring accommodations.   On every island the sea is never more than 20-30 kilometers from the sea and a cornucopia of beaches, so don’t forget your swim suit!


Trip Duration 8 days

Start & End Points 
Start:   Andros island, take morning ferry from Rafina port.  Meet in Athens for vehicle transfer to Rafina port (about 40 minutes).
End:  Santorini.  Daily flights and ferries from Santorini to Athens and other islands.

CHILDREN  This tour is not recommended for children under 16 years old

RATING  This tour is rated moderate.  Hikes average 5 hours a day walking at a moderate pace.

ISLAND HOPPING  You get to each island by ferry and a driver is there to meet you to take you to your hotel.

HIKING GUIDE VERSUS SELF-GUIDE  The advantages of a hiking guide is you do not have to figure out anything how to get from Point A to Point B.   The guide not only leads you in the right direction but he or she also enlightens your experience by providing information relating to the history and culture and flora and fauna on each day’s hike.   Additionally the guide carries provisions, such as, extra water, binoculars, first aid kit and snacks, although you are expected to carry your own water and picnic lunch.  For self-guided tours you are given a map and GPS device, but otherwise you are on your own carrying your own water and supplies.

HIKING LOGISTICS   The most strategic aspect to hiking in the Cyclades is the transfers.  Whether you opt for a guide or self-guided tour we ensure that you are transferred by a driver to the start point of each hike and that the driver is waiting for you at the end point as well.  We provide a mobile phone so that you are in contact with the driver.

BOOKING AGREEMENT  Participants are required to sign our company Booking Agreement as a condition of the tour.

WAIVER  Participants are required to sign our company Waiver as a condition of the tour


Day 1: Andros
Andros is the most northerly of the Cycladic islands and the second largest. For hikers, the has a rich network of walking paths known as “kalderimis” some of which are dirt, others paved, and many pass through the local walls built in Andriotic style alternating between small rocks and large vertical like rock plates.

Day 2: Andros
Seneti hike — the route’s terrain has high rocky cliffs and is pristine with no villages en route. Andros had many shipping magnates who built beautiful homes and appreciated culture. Visit the archaeology museum for an exquisite statue of Hermes form the 1st century BC.

Day 3: Mykonos
Catch the morning ferry from Andros to Mykonos, Greece’s most well-known island, and particularly famous for its sandy beaches. Today is a relaxing day with long beach strolls.

Day 4: Naxos
Hike sacred Delos island which lies about 20 minutes or so by boat from Mykonos. Delos was the political and religious centre of the Aegean and celebrated as the birthplace of Apollo. Wealthy merchants and bankers from all over the eastern Mediterranean lived in Delos. Afternoon ferry to Naxos.

Day 5: Naxos
This walk starts in Filoti where you take a peak inside Za Cave not far outside town. The route takes you on exquisite stone paths, through valleys, and past water mills, shady plain trees, and the 15th century fortified tower of Fotodótis. The day offers a true taste of Naxian countryside before ending in Apiranthos, the most charming mountain village on the island.

Day 6: Santorini
Your route is Fira, via Firostefani and Imerovigli, to Oia (pronounced E-ah). A portion of the hike takes you through these towns themselves, giving you the opportunity to admire modern Cycladic architecture along with timeworn churches. The path which hugs the spine of the ridge offers a spectacular view of the entire sea and caldera. Sunset wine tasting

Day 7: Santorini
Your hike starts in Kamari, a seaside town with black sand.  You take the switchback road up to Ancient Thira, about 45 minutes to the ticket entry window.  Then another 15 minutes to get to the site.  Ancient Thira has ruins from the 9th century BC onward.  On the return you ascend to Mt. Profitis Ilias, Santorini’s highest point at 1,857 feet.

Day 8: departures
Daily flights from Santorini to Athens



Participants Hiking Guide Self-Guided
1-2 4190 euros per person 2570 euros per person
3-4 2990 euros per person 2160 euros per person
5-6 2600 euros per person 2040 euros per person
7-8 2410 euros per person 1980 euros per person
Single Supplement 700 euros 900 euros

Tour cost is based on double occupancy.

For currency exchange rates, click here.


Hiking Guide Inclusions Self-Guided Inclusions
7 nights accommodations in 4 star hotels – see Accommodations tab 7 nights accommodations in 4 star hotels – see Accommodations tab
Daily breakfast at each hotel Daily breakfast at each hotel
Hiking guide – see details below
airport transfers
Athens – Rafina transfer Athens – Rafina transfer
Transfers to start point and from end point of each day’s hike Transfers to start point and from end point of each day’s hike
maps of the region maps of the region
boat to Delos and entry fee
entry fee to Ancient Thira
mobile phone with 10 euros card mobile phone with 10 euros card
Trip packet with useful information: what to see and do in each region, recommended tavernas, packing tips, phone numbers, etc. Trip packet with useful information: what to see and do in each region, recommended tavernas, packing tips, phone numbers, etc.
Gratuities, tips, VAT Gratuities, tips, VAT


Hiking Guide Exclusions Self-Guided Exclusions
Airfare to/from Greece Airfare to/from Greece
Airfare or ferry departure from Santorini Airfare or ferry departure from Santorini
Meals except breakfast Meals except breakfast
Trekking poles Trekking poles
Travel Insurance -see Extras tab Travel Insurance – see Extras tab


You have the same hiking guide throughout the tour.  He or she travels with you from Athens to Rafina and takes all ferries with you.  The guide leads you on all hikes from beginning to end. He or she carries provisions such as maps, first aid kit, extra water, snacks.  If there is a picnic lunch, you are expected to carry it and always carry your own water.  The guide finishes the duties for the day after dropping you off at your hotel. You are given a mobile phone for contact with the guides. The guides handle all logistics with transfer drivers.


Travel Insurance  For U.S. citizens, we are official agents of Travel Guard travel insurance and can book your trip insurance or provide you a policy quote.

Airport Transfer  For Self-Guide participants, opt for a transfer in our company vehicle from Athens Airport to your hotel.  Driver waits for you no matter if your flight is late and takes you directly to your accommodations.   170 euros per group for up to 8 passengers

Athens hotel   We can book your pre- and post-tour accommodations in Athens with a choice of fine hotels we patronize in the Plaka or Psirri neighborhood.

Licensed Guide at Delos   A private professional guide at Delos archaeology site can change your entire perspective about what is in front of you.  What looks like rubble comes alive in the presentation of a skilled guide.  Cost is 225 euros per group, excluding boat to Delos (20 euros) and entry fees (12 euros).

Santorini Cooking Class  Learn the inside wonders of the unique Cyclades cuisine.   Taste white eggplants and round-like-a-ball zucchini.  Wine tasting of five wines and gourmet lunch.  Lasts 4-5 hours.   180 euros per person.


Nissaki BeachAn indicative hotel for the Cyclades Donkey Paths tour is Nissaki Beach localed directly on the sea and within a ten minute walk to the harbor capital.

We select the accommodations based on quality, comfort, cleanliness, hospitality, location and charm. Most of the hotels on this tour are family owned and operated.

Hotels are included in the tour cost based on double occupancy. A single room entails an additional cost. Standard double rooms are provided but upgrade options are available.

All hotels are dependent on availability. In the event of no occupancy, we patronize comparable accommodations in the same location.

Request Links to Accommodations for Cyclades Donkey Paths


Click map to open in Google Maps

Overnight destinations and points of interest


This tour is also available for groups of more than eight persons. You can take the tour with the itinerary as listed or we can customize the tour’s destinations and activities to suit your party.

A group of eight participants travel in a company vehicle with staff driver who also acts as your guide. A group of 10-16 participants travel in either two company vehicles with staff driver/guides or one mini-coach. Groups larger than 16 participants travel in coaches or mini-coaches, led by a company tour leader who handles all logistics.

We offer innovative tours to large groups attending a congress, conference or corporate event.

See more information on the Groups page.

Contact us directly for price quotes and itineraries for your party’s special stay in Greece.


  • Hike the charming “kalderimis” dirt paths of Andros
  • Explore sacred Delos, one of Greece’s most treasured antiquities
  • Seaside dining in Little Venice of Mykonos island
  • Hike to Za cave and other footpaths on Naxos island
  • Walk on a pumice path in Santorini to Ancient Thira
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