Hiking in the Greek Isles route-map

Trip Details at-a-Glance

Cost From: $4795  
Length: 14 days
Arrive: Athens, Greece
Depart: Santorini, Greece
Lodging: 13 nights hotels and country inns
Meals: All meals included except 2 dinners
Activity: Hiking / Trekking, Archaeology, Cultural Adventures
Trip Level: 7 hiking days on moderate to strenuous trails, some steep sections, 4-6 hours a day, van support (for luggage or if you wish to skip a day's hike)


  • 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, including freshly caught seafood and kopanisti, a soft and peppery goat cheese

I'm till basking in the glow of this glorious adventure. It was the perfect combination of natural beauty and cultural exploration. There were amazing hikes, quaint towns, and beautiful beaches. Every bite of food was delicious. The hotels were lovely. All of our Greek hosts were warm and gracious. It was my first time in Greece, and because of this trip, it won't be my last. As in all Wilderness trips I've taken, I felt like I had the insider track and got to see places I'd never been able to discover or have access to on my own.Susanne R.—Brewster, NY

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.

Greece casts a bewitching spell, and in the stunning beauty of the Cyclades, an archipelago named for the circle it forms around the sacred island of Delos, our hiking adventure brings you to the tranquil realms of Tinos, Naxos, and rugged Amorgos, where bougainvillea-draped hill villages are suspended above the gleaming Aegean. Our paths lead to bright blue-domed churches, up to cliff-perched monasteries, and through tiny whitewashed villages. Soak up the good life with picnics on verdant hillsides and swims in the warm azure seas. Our journey finishes on legendary Santorini, its town built atop the caldera’s rim.

Itinerary at a Glance

For a more complete description, Download Full Detailed Itinerary

Days 1-3
Athens / Tinos

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

Days 4-5
Sacred Delos / Mykonos / Tinos

On Delos, discover a vast open-air archaeological museum of ruins, then explore cosmopolitan Mykonos, with its winding alleys, windmills, and picturesque whitewashed villages.

Days 6-7
Naxos / Chora / Mt. Zas

Crossing the Aegean to Naxos, an island graced with vineyards and olive groves, explore the seaside pathways of Chora, the main town, and hike up Mt. Zas to a sacred cave with stunning views.

Days 8-11

Our hikes on gorgeous Amorgos lead along a lovely footpath to Chosoviotissa, a gleaming 11th century monastery clinging to a towering cliff, and to sunny beaches where warm, crystal-clear waters beckon for swims in the sea.

Days 12-14

In Phira, the sky-high capital, enjoy wine tasting and a visit to Akrotiri, a fascinating Minoan Bronze Age archaeological site with remarkably well-preserved frescoes. Depart on Day 14.

For a more complete description, Download Full Detailed Itinerary

Optional Extensions

If you would like to continue your adventure, we offer the following extension:

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



May 15-28, 2016
Jun 1-14, 2016
Jun 29-Jul 12, 2016
Aug 31-Sep 13, 2016
Sep 14-27, 2016

Trip Cost

Prices are for 2016
$4795 (8-16 members)
$4995 (4-7 members)
Single supplement: $420
Forced single supplement: $210
more on pricing

Extension Costs
Archaeological Sites of Classical Greece Extension
   from: $1550

Trip Payment Schedule

At time of reservation: $600
90 days prior to departure: Balance

Cancellation and Transfer Fee Schedule

Up to 91 days prior to departure: No charge!
61-90 days prior to departure: 25% of trip cost
46-60 days prior to departure: 50% of trip cost
45 days or less: 100% of trip cost

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
  • A glass of wine or beer with dinner
  • 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 14, 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.).

Arrival & Departure Information

You are responsible for your own transportation to the arrival and from the departure cities listed below. For more detailed information, including transfers, please download the Detailed Itinerary.

Please do not purchase your tickets until you are confirmed on the trip. Once your tickets have been purchased, please send us a copy of your airline schedule.

2016 Departures

Meeting Place:
Athens, Greece
Date: Day 1

Suggested Arrival Airport:
Athens, Greece (airport code: ATH)
Suggested arrival time: anytime
Santorini, Greece
Date: Day 14

Suggested Airport for Departure:

Thira Airport Santorini, Greece (airport code: JTR)

Divani Palace Acropolis

Divani Palace Acropolis

Day 1 (1 night), Athens, Greece

Exploring the ancient history of the Parthenon and the museums of Plaka is easy from the Divani Palace Acropolis. Set below the Acropolis, rooms at ...
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Hotel Voreades

Hotel Voreades

Days 2 to 5 (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 6 to 7 (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 8 to 10 (3 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 12 to 13 (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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Extension Accommodations

If you would like to view the accommodations offered with our extensions option:

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).

Karolos Merlin

Karolos Merlin, or “Charles” as his English friends call him, has been leading treks through the Greek countryside for over 15 years. Born to an Austrian mother and Greek father of English origin, he lived in Austria until he was 7, when his family relocated to Greece. After meeting ...
Click here for a full bio and list of all upcoming trips

Dimitra Panagiotopoulou

Dimitra Panagiotopoulou’s love of adventure was sparked in childhood as she followed her father and grandfather on hunting expeditions into the Greek woods. After completing her education, she worked as a sales manager at a big company for over a dozen years, but memories of youth and a love ...
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Katerina Vasileiou

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 ...
Click here for a full bio and list of all upcoming trips

Kostas Vasileiou

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 ...
Click here for a full bio and list of all upcoming trips

Optional Extensions

If you would like to continue your adventure, we offer the following extension:


Archaeological Sites of Classical Greece Extension

Delphi, Olympia & Beyond

Cultural Adventures
5 days  -  Level 1

Client Comments

I'm till basking in the glow of this glorious adventure. It was the perfect combination of natural beauty and cultural exploration. There were amazing hikes, quaint towns, and beautiful beaches. Every bite of food was delicious. The hotels were lovely. All of our Greek hosts were warm and gracious. It was my first time in Greece, and because of this trip, it won't be my last. As in all Wilderness trips I've taken, I felt like I had the insider track and got to see places I'd never been able to discover or have access to on my own. Susanne R., Brewster, NY We loved this trip. It was a wonderful combination of hiking, exploring archaeological and historical sites, swimming in the Aegean Sea, meeting wonderful people, from hotel hosts to friendly taverna cooks and local residents. We were constantly amazed at the quality (and quantity!) of food, wine, and other treats. Kate A., San Francisco, CA Greatest trip I have taken. Everything exceeded my expectations. This trip was on my ‘bucket list’ and I'm so glad to have taken it with WT. Jim H., Montgomery Village, MD This was one of the most incredible experiences of my life. I have already begun recommending Wilderness Travel to friends and family and am very eager myself to go on another WT trip! Kyla M., Greenville, TX This was a trip for the ages—excellent guide, food, planning, knowledge...I will never forget it. Catherine S., Bethesda, MD Fabulous trip in all respects! Loved the combination of busy and less busy islands, of hiking and archaeology, of very unique B&B's and more modern hotels, and of a vast menu of delicious Greek food and drink. Weezie J., Concord, MA Wilderness always does an excellent job with their trips. This is my first hiking trip and I am 60+. The variety of food during our meals was excellent. Christine B., New York, NY We had a great time and highly recommend this trip for anyone who's never seen these stunningly beautiful isles. Great leadership, Wonderful food—a must-do! Bill G., Corrales, NM Great food, beautiful scenery, and I felt we were seeing the real Greece and not just the tourist areas. I had a great time! David S., Carson City, NV Another exceptional trip with WT. Everything went smoothly down to the last detail, which made for easy travel and allowed us to focus on the culture, beauty, and charm if the Greek Isles. Can't wait to book my next WT adventure! Laurie D., Basalt, CO This is the first ever group travel experience my husband and I have ever had, and it was wonderful! We enjoyed the people, the leaders, the scenery, the food, the hiking, and the sites we saw. Dena S., Memphis, TN We were very impressed with the overall experience. It was a nice blend of hiking and leisure. And the meals were epic! We had no idea we would be experiencing such a culinary adventure. Cheryl L., Parkdale, 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 A fun trip, every day was a gift. Dawn M., Hillsboro, OR 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 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 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 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 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 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 Lots of fun! Beautiful sites, excellent food, great company! Liz K., San Francisco, CA We saw wonderful parts of the Greek isles that we would never have seen on our own. Ollie H., Castle Rock, CO I'm so glad we opted to explore the Greek isles the Wilderness Travel way rather than by luxury cruise! Wallace I., Honolulu, HI 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 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 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