Walking tours


Greece Cyclades Island Walk

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Greece Cyclades Island Walk

  • Location: Greece
  • Duration: 9 Days/8 Nights (*13 Days/12 Nights with the Crete extension)
  • Departing from: Athens, Day 1
  • Tour finishes: Santorini, Day 9 (*or Chania Day 13)
  • Departures 2018: May 22 -- TUESDAY departure; 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. Crete extension: €1,650 per person based on double occupancy with 1 and minimum 3 people for 4 nights. Single supplement €160.

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.
* Extend your trip with 4 days on the beautiful and rugged island of Crete! It's a quick ferry ride from Santorini, and you'll learn all about the powerful and enigmatic Minoans, considered the first real great civilization of Western Europe!

Greece Cyclades Island Walk itinerary

Day 1 (TUESDAY May 22 departure)

Arrival in Athens Transfer on your own from Athens International airport to our hotel in the city center. Meet your guides at 6:30 p.m. for a drink on the rooftop bar of your hotel and then dinner nearby. Overnight in Athens. Hotel and dinner included.

Day 2 (Wednesday)

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 (Thursday)

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 at the hotel pool with a cold drink. Overnight Tinos. Hotel, breakfast, lunch and dinner included.

Day 4 (Friday)

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. We end our hike in a charming small town where we visit a distillery of locally-made "citron" liqueur. Afterwards, rub elbows with the locals as we have dinner at a very local taverna. Pass the ouzo and let the fun commence! Overnight Naxos. Hotel, breakfast and dinner included.

Day 5 (Saturday)

We have a special treat for you today as we board a private catamaran to explore the nearby "Small Cyclades" islands. Pack a swimsuit and relax on deck as we see the sights from the high seas. Weather permitting, we'll disembark on several of the islands to beachcomb, explore, and enjoy an ice coffee in the tiny villages we encounter. Tonight is a free night, so feel free to explore the city’s restaurants on your own or with friends. Overnight Naxos. Hotel, breakfast and lunch included. Dinner not included.

Day 6 (Sunday)

Naxos: Mount Zeus!
We begin the day with a van shuttle to the center of the island for a hike up mighty Mount Zas (Greek for Zeus). It's a steep climb but short, and we'll have sweeping 360 degree views from the summit. The Greek God of Gods was supposedly raised here (he was "born" on Crete, they say) to keep him out of trouble with his father, Kronus. Back at the hotel, watch the sun set behind 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 7 (Monday)

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 (Tuesday)

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.

Day 9 (Wednesday)

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 4-night 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. And transport to Heraklion for those on the extension.


€1,650 per person based on double occupancy with 1 guide for 4 nights and minimum three people. Single supplement €160.

Day 9 (Wednesday May 30)

Take the morning to wander the streets of colorful Oia or maybe just relax by the pool, and then take a 5 p.m. hydrofoil ferry to Heraklion, the capital city of the island of Crete. Enjoy a drink on the rooftop of our hotel before heading out for dinner at one of the city's most sought-after dining experiences. Overnight in Heraklion. Hotel, breakfast and dinner included.

Day 10 (Thursday May 31)

Visit the fascinating archaeological museum this morning, featuring some of the most interesting items ever found from the Minoan and Mycenean occupation of the island thousands of years ago. We generally opt NOT to visit the ruins of Knossos since it has been overrun by tourists and is not a very pleasant experience, but we can add it into the itinerary if the group wants to go. Otherwise, we take a short van transfer to the trailhead for our hike through the countryside to an ancient Minoan site. We'll be far from the tourist hordes and can relax with a delicious lunch on a leafy terrace afterwards. After the hike we go to the nearby and lovely Kapsaliana Village Hotel, a beautifull restored farm complex with a swimming pool and excellent restaurant.  Hotel, breakfast and dinner included.

Day 11 (Friday June 1)

We continue our drive west this morning with a transfer to Chania, one of the most delightful port towns in the Mediterranean. Our itinerary can stay loose today, as we can decide together if we want to spend the day on a beach, or visit a winery for lunch and a tasting, or both! In the same spirit of flexibility, we've left the evening "free" so you can do as you please. Eat light and have an early night, or splash out at one of the bustling seafood restaurants along the port. Hotel and Breakfast included. Dinner not included.

Day 12 (Saturday June 2)

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 one last dinner together at one of the city's colorful restaurants. Overnight Chania. Hotel, breakfast and dinner included. 

Day 13 (Sunday June 3)

Depart at your leisure today. We haven't organized any transport to the Chania airport as there are flights throughout the day and we may not all be leaving at the same time. You'll find several flights to Athens throughout the day, or else check the low-cost carriers for direct flights to the U.K., Italy, etc. You could even take a bus (2 hours) back to Heraklion if your ideal flight happens to leave from there. Breakfast 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, 2 lunches 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. 
*Crete extension includes: 4 nights accommodation, 4 breakfasts and 3 dinners; visits and transfers as noted in the itinerary.

Not included: air travel to Greece; flight from Santorini (or Chania) 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 (or Chania, for the Crete extension). Continuing flights are not included since many people have plans that do not involve a return to Athens. Both airports are well connected to Athens as well as European hubs via the major carriers (Aegean, Olympic) as well as low-cost airlines like Ryan Air and Easy Jet.

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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