Walking tours


Greece Cyclades Island Walk

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Greece Cyclades Island Walk

  • Location: Greece
  • Duration: 9 Days/8 Nights
  • Departing from: Athens, Day 1
  • Tour finishes: Santorini, Day 9
  • Departures 2017: May 18 -- THURSDAY departure; and private departures.
  • Price 2017: Euro €3,150 per person based on double occupancy and minimum 3 people. See our Guaranteed Departure policy. Single Supplement Euro €320.
  • Departures 2018: May 19 and private departures.
  • Price 2018: Euro €3,150 per person based on double occupancy and minimum 3 people. See our Guaranteed Departure policy. Single Supplement Euro €320.

The Cyclades island chain is known the world over for its natural beauty, rich history, traditional villages and fabulous food. We have developed an itinerary that flows beautifully, is not too hectic, and allows us to really explore and experience three unique islands: Tinos, Naxos, and amazing Santorini. We take you on gorgeous walks to the best spots, including the “hidden” interior of the islands where local culture and traditions still thrive.

Greece Cyclades Island Walk itinerary

Day 1 (Saturday)

Arrival in Athens Transfer on your own from Athens International airport to our hotel in the city center. Meet your guides at 7:00 p.m. for a short walk to the Plaka – the historic center of Athens – for a drink overlooking the Acropolis followed by dinner at a local taverna. Overnight in Athens. Hotel and dinner included.

Day 2 (Sunday)

The Acropolis – ferry to Tinos. After breakfast we have a guided visit of the Acropolis, including the world-famous Parthenon, so you can learn about the city's 4,000-year history and understand its importance in our world today. We then have a one-hour transfer to the port of Rafina, where we’ll have lunch and then depart for the island of Tinos by high-speed catamaran (approx. 2.5 hours). Tinos is one of the larger islands of the Cyclades group and yet one of the least visited by foreign tourists. You’ll love our quiet hotel in the heart of the old town. Overnight Tinos. Hotel, breakfast and dinner included.

Day 3 (Monday)

Explore Tinos. Our walk takes us up into the hills along ancient terraces and tracks, and past some of the thousands of dovecotes brought to the island by the Venetians in the 17th century. We stop for coffee in a cute little village before continuing on to Tripotamo, where we help make lunch with our wonderful host, who uses ingredients from her own garden. After lunch we walk down to the port of Tinos, with views out over the turquoise Aegean Sea and the nearby islands as we go. Take some time in town to admire the famous church, peruse the shops, or relax with a cold drink at a sidewalk café by the old port. Or, head back to the hotel and have a swim at the sandy beach! Overnight Tinos. Hotel, breakfast, lunch and dinner included.

Day 4 (Tuesday)

Transfer to Naxos and enjoy the lush interior. This morning we take a ferry to the island of Naxos, capital of the Cyclades Island chain for 400 years when the region was under Venetian rule. We check into the hotel and then depart for a lovely walk through the green valleys of the island, the most verdant in the entire island chain. The walk takes us past a monumental kouros statue that was abandoned in the 8th century BC, a mute testament to the island’s once-thriving limestone works. Later this afternoon, watch the sunset from the Portara, the unfinished temple of Apollo which dominates the harbor entrance.  Enjoy dinner tonight in a restaurant along the harbor. Overnight Naxos. Hotel, breakfast and dinner included.

Day 5 (Wednesday)

We have a special treat for you today as we board a private catamaran (or sailboat) to explore the nearby "Small Cyclades" islands. Pack a swimsuit and relax on deck as we see the sights from the high seas. We'll disembark on several of the islands to beachcomb, explore, and enjoy an ice coffee in the tiny villages we encounter. Overnight Naxos. Hotel, breakfast and dinner included.

Day 6 (Thursday)

Naxos: churches and small towns
We begin the day with a van shuttle to the center of the island and have a beautiful walk past a number of Byzantine churches. We continue to the former capital of Chalki, where we visit one of the oldest distilleries of kitro, a local liqueur. Enjoy a Greek coffee in the village square before resuming your walk through the olive groves, past a handful of ancient churches to a special spot for lunch under the shade of a massive oak tree. Tonight is a free night, so feel free to explore the city’s restaurants on your own or with friends. Overnight Naxos. Hotel and breakfast. Dinner not included.

Day 7 (Friday)

Transfer to Santorini and hike the crater rim. We have a few hours free  this morning to explore the labyrinthine streets and Venetian citadel of Naxos town before boarding the ferry to Santorini. The afternoon walk is one of the most spectacular in the world, as it takes you around the rim of the island’s volcanic crater. Blown apart by a massive eruption in 1500 BC, the steep volcanic cliffs are surmounted by gleaming white-washed villages. The ferry drops us outside of the colorful town of Fira, a 3-hour walk from our hotel in Oia (pronounced “Ee-ah”). Enjoy the dazzling sunset from the terrace of our hotel before heading into town on foot for dinner together. Overnight Santorini. Hotel, breakfast and dinner included.

Day 8 (Saturday)

The ancient Greek city of Thira.Transfer to the other side of the island this morning for a brisk morning walk. The landscape is completely different but the views are just as beautiful. We begin with a steep climb and then explore the ruins of ancient Thira, one of the oldest settlements in the Mediterranean. Delightfully free of tourists, the site offers an interesting view into the ancient cultures that once dominated the region. Afterwards, head down to the coast and tuck into a fresh seafood lunch by the sea. There’s time for a swim today, so bring your suit!  We return to our hotel after lunch and then get together for one final dinner in lovely Oia. Overnight Santorini. Hotel, breakfast and dinner included.

Da 9 (Sunday)

Our trip ends this morning with independent departures to the airport or other areas of Greece. You can end your trip here or else join us for a 3-day extension to the nearby island of Crete. Once home to the powerful and mysterious Minoan civilization, the island remained independent until the 20th century and still retains a cultural identity all its own. Santorini is served by Aegean and Olympic Airlines to Athens as well as by other carriers which fly directly to European hubs (see Ryan Air and Easy Jet for connections to Paris, Rome, Frankfurt, etc.). Breakfast included.


€1,050 per person based on double occupancy with 1 guide for 3 nights. Single supplement €120.

Day 1

we will fly to Heraklion directly from Athens this morning, arriving around lunch time in the island’s capital city. Have lunch together and then set out to explore the ruins of the Minoan city of Knossos or the small but fantastic museum in the heart of the old port. Overnight in Heraklion. Hotel, breakfast and dinner included.

Day 2

A short van transfer takes us to the trailhead for our hike through the countryside to another ancient Minoan site.  Along the way, pass a 2,000-year-old olive tree! After the hike we continue our drive along the coast to Chania, one of the most delightful port towns in the Mediterranean. Overnight Chania. Hotel, breakfast and dinner included.

Day 3

Our last hike is through the dramatic Imbros Gorge, one of the longest in Europe. We’ll have lunch by the sea and then shuttle back to Chania for a swim or a short walk through town. Enjoy dinner tonight at one of the fabulous seaside restaurants. Overnight Chania.  Hotel, breakfast and dinner included. 

Activity rating: 2.5 - 3 out of 5 = Moderate: Rolling, rocky terrain but the hikes aren't that long. Daily activity usually around 3-4 hours, sometimes in the morning and sometimes in the afternoon (depending on ferry schedules between islands). Max distance 11 kms. Note: although we do our best to adhere to the schedule listed above, this itinerary is subject to change for numerous reasons beyond our control.

Trip Cost Includes: 8 nights accommodation; 8 breakfasts, 1 lunch and 7 dinners; guided visit of Athens and all entrances as per itinerary; all ferry, van and luggage transfers as per itinerary; at least one Customwalks guide. 

Not included: air travel to Greece; flight from Santorini at the end of the trip; airport/hotel transfers; travel insurance; beverages other than water at meals; and items of a personal nature. 

Booking: e-mail us at info@customwalks.com to receive a booking contract (or use the 'Contact Us' link at the top of this page), or click on the 'Book Now' button to the right.

Insurance: We highly recommend the purchase of Trip Insurance. We recommend “Travel Guard” to our North American clients, just click on the logo below.  Australian, New Zealander, and British travelers, please consult your insurance brokers.

travel Guard insurance

Getting There: the trip starts in Athens, which is easily accessible via international flights.

Air: Athens airport receives both domestic and international flights, through European hubs such as London, Paris, Frankfurt, Amsterdam, Munich and Brussels.

Getting Away at the End of the Trip: the trip ends after breakfast on the morning of Day 9 in Santorini. Continuing flights are not included since many people have plans that do not involve a return to Athens.

If you book a trip with us you will receive detailed information about how to get to and from the trip, and of course you can e-mail us with any questions.

5.00 out of 5
Ratings based on 2 Verified Reviews

Average ratings
Quality of itinerary
Food quality & variety
Value for money
Right amount of activity
Overall satisfaction

by Muffinman from Canada
Posted Nov 07, 2016

You can never go wrong when you go to the Greek Islands. The scenery is beyond belief and the weather is always pleasant. We have been to this area a number of times and it keeps calling us back. The Guides are all very professional and extremely friendly and helpful. This was one of our most rewarding and exciting experience and we would highly recommend this trip if you are looking for adventure and exercise.

by PBrodie from Boston, MA USA
Posted Nov 06, 2016

We absolutely loved this trip. It had its mix of great hiking, historical sites, incredible beauty and relaxing days. Santorini was astonishingly beautiful, had sites that are some of my favorite in the world. I remember Tinos for the cooking class in the mountains and the most friendly family run hotel. We have travelled to Greece twice and this was by far our favorite.

You can never go wrong when you go to the Greek Islands. The scenery is beyond belief and the weather is always pleasant. We have been to this area a number of times and it keeps calling us back. The Guides are all very professional and extremely friendly and helpful. This was one of our most rewarding and exciting experience and we would highly recommend this trip if you are looking for adventure and exercise.
by Muffinman from Canada

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