greek islands hiking tour cyclades tinos amorgos mykonos santorini

Hill village, Cyclades Islands

Traditional villages are one of the delights of the sun-splashed Cyclades Islands. Our coastal hikes bring us across ancient footpaths on the islands of Tinos, Amorgos, Mykonos, and Santorini.

Photo by Johanna Huber / Fototeca 9x12

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Hiking in the Greek Isles

Hidden Trails and Golden Beaches of the Cyclades

Hiking in the Greek Isles route-map

Trip Details at-a-Glance

Cost From: $4995  
Length: 13 days
Arrive: Athens, Greece
Depart: Santorini, Greece
Lodging: 12 nights hotels and country inns
Meals: All meals included except 2 dinners
Activity: Hiking / Trekking, Archaeology, Cultural Adventures
Trip Level: 9 hiking days on moderate to strenuous trails, some steep sections, 4-6 hours a day, van support


  • Hike the beautiful Cyclades Islands of Tinos, Naxos, and Amorgos
  • Glorious Santorini, with its huge caldera, and sacred Delos, holy island of the ancient Greeks
  • Delicious Mediterranean cuisine, traditional villages, cliff-top monasteries

This was absolutely one of the best trips I have ever taken in my life. I loved every second of it and did not want to come home!Jenny G.—San Diego, CA

Choosing the Right Trip

We work hard to help you choose the right trip for you, paying attention to your individual interests, abilities, and needs. If you have questions about the level of comfort or any of the activities described in this itinerary, please contact us.


We are proud to have an exceptionally high rate of repeat travelers. For more information, we would be happy to put you in touch with a client who has traveled with us.

Departure Notes

Once you have signed up on the trip, we send a complete packing list, relevant health information, and required travel documents.

Greece casts a bewitching spell, with its honey-colored isles fragrant with frangipani and encircled by azure seas. In the stunning beauty of the Cyclades, an archipelago named for the circle it forms around the sacred island of Delos, we explore on foot in Tinos, Naxos, and rugged Amorgos, each a tranquil realm of bougainvillea-draped hill villages suspended above the gleaming Aegean. As we hike each day past blue-domed churches, up to cliff-perched monasteries, and through tiny whitewashed villages, the “good life” of sunny Greece surrounds us, with picnics on verdant hillsides, swims in the sea, and meals al fresco on taverna verandas, a chance to try local specialties such as tyropita (savory cheese pastry), fresh grilled sardines, eggplant drizzled with honey, and Naxos' sweet yellow potatoes, famous all over Greece. Our journey finishes on legendary Santorini, with its white villages clinging to the cliffs.

Itinerary at a Glance

For a more complete description, Download Full Detailed Itinerary

Days 1-2
Athens / Tinos

From Athens, we ferry to craggy Tinos, where we hike a kalderimia, or cobbled mule path, to picturesque villages and along a Roman road up to the great Venetian fortress of Santa Elena.

Days 3-4
Sacred Delos / Mykonos / Tinos

Ferrying to Delos, we stroll through a vast open-air archaeological museum of ruins, then continue to Mykonos, with its winding alleys and fishermen’s dwellings, before returning to Tinos.

Days 5-6
Naxos / Chora / Mount Zas

We cross the Aegean to Naxos, with its vineyards and olive groves, to explore the twisting lanes of Chora, the main town, and hike up Mt. Zas to a sacred cave with a marvelous view.

Days 7-10
Amorgos / Tholaria

Beautiful Amorgos has golden beaches and a well-designed network of cobbled paths connecting its villages. One of our hikes leads to the great monastery of Agios Theologos, while another brings us to Mt. Krikelos, then down to Levrossos Beach.

Days 11-13

Approaching Santorini by ferry, we behold the dramatic sight of the five-mile-wide caldera of this collapsed volcano, its towns built atop the caldera’s rim. In Phira, the sky-high capital, we enjoy wine tasting and a visit to Akrotiri, a fascinating Minoan Bronze Age archaeological site with remarkably well-preserved frescoes. Depart on Day 13.

For a more complete description, Download Full Detailed Itinerary

What the Trip is Like

This trip is Level 3+, Moderate to Strenuous. Hiking times vary from 3 to 6 hours on moderate trails. Although you carry only a daypack on the hikes, be prepared for steep ascents and descents and some sections that cross uneven terrain and rough or rocky trails. Some days are a full day of hiking; others involve a half day or more exploring one of the towns on foot. On some days, we taxi or take a local bus to a starting point for our hike and also use a taxi or local transport to return to our night's lodging. Travel between islands is by ferry (or high-speed catamaran, if it is available); ferry rides are likely to be an average of two to five hours. On a couple of days, ferry rides may take longer due to weather or schedule changes. We do our best to use the fastest ferries, but this is not always possible. There are many opportunities for swimming on this trip.
Accommodations are in small local hotels chosen for their atmosphere and location.  Although the rooms in these pensions are not always of uniform or international size, our leaders always try their best to assign rooms in a fair way so that all participants experience an equal advantage throughout the trip as a whole. We enjoy our lunches picnic-style or at small tavernas. Our dinners also feature local food and a chance to sample traditional specialties of the Cyclades. Some evenings we dine in our pensions and other nights at local restaurants. The delicious cuisine of these islands comes straight from the land or the sea. Please note that in Greece, the dinner hour is considerably later than what it is in the US. We do our best to secure early reservations for our groups, but most often the evening meal will be at 8:00 pm.

For your own enjoyment, we recommend you make a special effort to be in good physical condition for the trip. Daily walking and/or regular hiking (or using a stair-climbing machine at your gym) are excellent preparatory exercises. You should wear sturdy, well-broken-in hiking boots for maximum comfort on the trail.

Explanation of Trip Levels


Departures & Leaders

Sep 14-26, 2014  Kostas Vasileiou
May 16-29, 2015  Katerina Vasileiou
Jun 3-16, 2015  Kostas Vasileiou
Jun 30-Jul 13, 2015  Kostas Vasileiou
Sep 2-15, 2015  Kostas Vasileiou
Sep 16-29, 2015  Kostas Vasileiou

Trip Cost

Prices are for 2014
$4995 (8-16 members)
$5195 (4-7 members)
Single supplement: $375
Forced single supplement: $210
more on pricing

Trip Cost Includes:

  • Expert leadership of a Wilderness Travel Trip Leader and local guides
  • Accommodations in hotels and small comfortable inns
  • All meals included except 2 dinners
  • Entrance fees to sites
  • Ground and boat transportation from meeting until departure as noted in the Full Trip Brochure

Trip Cost Does Not Include:

International airfare, airfare from Santorini to Athens on Day 13, hotel transfers to/from airports other than the designated group flights, any meals not specified after each itinerary day in the Full Trip Brochure, airport departure taxes, optional tipping or gratuities to leaders or staff, additional hotel nights that may be necessitated by airline schedule changes or other factors; pre-trip expense of medical immunizations (if any), travel insurance or passports; and other expenses of a personal nature (alcoholic beverages, laundry, etc.).

Trip Payment Schedule

At time of reservation: $500
120 days prior to departure: 20%
60 days prior to departure: Balance

Cancellation and Transfer Fee Schedule

More than 90 days prior to departure: No charge!
46-90 days prior to departure: 25% of trip cost
45 days or less: 100% of trip cost

Hotel Voreades

Hotel Voreades

Days 1 to 4 (4 nights), Tinos, Greece

This 9-room boutique hotel is in a traditional stone-built house on the beautiful island of Tinos near the old port. The hotel has all the modern ...
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Hotel Naxos Beach 1

Hotel Naxos Beach 1

Days 5 to 6 (2 nights), Naxos, Greece

A 20-minute walk from Naxos town, this hotel has small but comfortable rooms spread around a garden and a fantastic location next to a nice beach. ...
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Vigla Hotel

Vigla Hotel

Days 7 to 10 (4 nights), Tholaria, Greece

On the beautiful, mountainous island of Amorgos, we stay at the family-run Vigla Hotel, set on a hill in the ancient whitewashed village of Tholaria ...
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Caldera's Lilium Villa

Caldera's Lilium Villa

Days 11 to 12 (2 nights), Santorini, Greece

The outstanding feature here? Undoubtedly the breathtaking Aegean views and incredible sunsets of Santorini’s spectacular caldera. Guest rooms ...
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Note: Listed above are our signature accommodations for this trip. Although it is highly unlikely, we may make substitutions when necessary.

Our Trip Leaders

Here are the Trip Leaders scheduled for this journey (please note that leader assignments are subject to change).

Kostas Vasileiou

Departure Dates: September 14-26, 2014, June 3-16, 2015, June 30-July 13, 2015, September 2-15, 2015, September 16-29, 2015

Kostas Vasileiou was born and raised in Ioannina, Greece, and now lives in the historic village of Kipi in the Vikos Gorge. He holds a professional mountain guide's licence from the Alpine Club of Greece and has also led trekking expeditions in Nepal. "Being a Trip Leader puts me in contact with ...
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Katerina Vasileiou

Departure Dates: May 16-29, 2015

Katerina Vasileiou, the daughter of WT Trip Leader Kostas Vasileiou, grew up in a family of mountaineers, and has hiked and trekked her entire life. Her love of nature and culture led her decide on a career in travel, and since 2007 she has been an assistant leader on our Hiking in the Greek ...
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Client Comments

This was absolutely one of the best trips I have ever taken in my life. I loved every second of it and did not want to come home! Jenny G., San Diego, CA I will never forget this experience. It was everything I had hoped for: the chance to be outdoors in nature, adventure, fun, and beyond that, an opportunity to lose myself completely in the beauty of the country and the warmth of its people. Cathy C., Sonoma, CA Your company is great to work with, as always. This was my third and favorite trip so far, and I’m not done yet! Cathy C., Sonoma, CA, I'm so glad we opted to explore the Greek isles the Wilderness Travel way rather than by luxury cruise! Wallace I., Honolulu, HI We saw wonderful parts of the Greek isles that we would never have seen on our own. Ollie H., Castle Rock, CO Lots of fun! Beautiful sites, excellent food, great company! Liz K., San Francisco, CA I describe this to my friends as a trip in which I hiked and ate my way across the Greek Islands. The food was awesome, the hiking was beautiful, and the leaders were outstanding! Gwynne W., Lebanon, NJ The trip was outstanding in so many respects: the organization and efficiency, the guides' leadership and knowledge, the choice of sites to visit and stay, and more. Al D., Twin Lakes, CO
The trip was a wonderful adventure in a beautiful corner of the world. The quality of the preparation and the skill of the guide made it a very relaxing holiday. We put our minds to rest and let our feet do the work. We loved it!
Kim O., Bellevue, WA The trip was fantastic! Kostas and Wilderness Travel allowed us to enjoy our private journey with our kids to give us memories to last a lifetime. Linda B., Madison, WI We hiked along trails blanketed with wildflowers to spectacular cliffs; explored the narrow streets, small museums, and shops of whitewashed villages perched above the sea; visited simple chapels with ancient icons and frescos; lunched on secluded beaches; explored ruins at sites that have been inhabited for 4,000 years or more. To a person, the Greeks could not have been friendlier or more welcoming to us. Niles B., Madison, WI Getting to taste 168 different Greek recipes on the trip was an adventure in itself! The trip really ought to be called 'Eating in the Greek Isles, with some hiking.' Susan J., Cochrane, Alberta A fun trip, every day was a gift. Dawn M., Hillsboro, OR Hiking the Greek Isles and swimming and boating the Aegean Sea is a trip I dreamed about—a trip that came true with this spectacular Wilderness Travel trip. Robert M., Great Falls, VA