Walking tours


Greece Cyclades Island Walk

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  • 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 2019: May 28th and Sept. 24th (TUESDAY departure). Private departures available, please contact us for details.
  • Price 2019: Euro €3,200 per person based on double occupancy and minimum 3 people. Single Supplement Euro €320. Crete extension: €1,700 per person in double occupancy and minimum 3 people for 4 nights. Single supplement €160. Two guides accompany departures of 9 or more people.
  • Departures 2020: May 26 and Sept. 22 (TUESDAY departure). Private departures available, please contact us for details.
  • Price 2020: Euro €3,250 per person based on double occupancy and minimum 3 people. Single Supplement Euro €320. Crete extension: €1,750 per person in double occupancy and minimum 3 people for 4 nights. Single supplement €160. Two guides accompany departures of 9 or more people.

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 departure)

Arrival in Athens: transfer on your own from the Athens International airport to the Hotel Herodion 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 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, the family-run Onar Studios, 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 in Naxos at the lovely Hotel Grotta. Hotel, breakfast and dinner included.

Day 5 (Saturday)

Catamaran Trip! 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 interior of the island this morning to Pyrgos, one of the prettiest villages on the island and former capital during medieval times. The landscape is completely different from the crater side, but the views are just as beautiful. Have a look around the village and then start a climb up to the monastery of Prophet Elias, which sits at the highest point on the island and has commanding views. From there, continue to 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)

Departures. 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)

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 at the eco-friendly Olive Green HotelHotel, breakfast and dinner included.

Day 10 (Thursday)

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 transfer to the beautiful town of Rethymno, one of the island's most charming towns. Dine on fresh fish tonight at a lovely restaurant along the old harbour. Overnight Naxos. Hotel, breakfast and dinner included.

Day 11 (Friday)

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. Our hotel is located right on the old port with perfect views over the surrounding town from the rooftop terrace. Overnight in Chania at the Amphora Hotel. Hotel and Breakfast included. Dinner not included.

Day 12 (Saturday)

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)

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 Level 3 = Moderate:
In general: This is a Moderate tour for fit hikers, and a little challenging but do-able for not-so-fit hikers.
Terrain: Rolling to hilly terrain with frequent climbs and descents, often over rocky terrain. May have some short, relatively steep climbs and descents. 
Actual walking time: between 2-5 hours per day, mostly in the morning but also in the afternoon.
Distances: Usually between 8 and 12 kms/5 and 7 miles. Max distance is 14 kms/8 miles.
Surfaces: Trails consisting of mostly compact earth, gravelly earth, and sometimes dirt-gravel roads and on occasion rocky and uneven trails. 
Footing: Good, but on occasion you have to pay attention to where and how you place your feet. Proper hiking shoes with thick soles with good treads are required. Sport sandals, running shoes and tennis shoes are not adequate.
Specifics: the hikes are all 3-5 hours long and are mainly on rocky terrain. The hike to the summit of Mt. Zeus, while not long, involves a sustained uphill (3 km) and then an equal distance back down, involves an elevation gain (and then loss) of 400 meters (1,200 ft.). The longest distance is 10 km/6 mi. (day 1 on Tinos) and 9 km/5.5 mi. around the crater rim on Santorini.
Hiking Poles: Recommended but not required, but if you habitually use hiking poles then you will find them helpful.  
Compared to the Cinque Terre: These tours are easier than the hikes in the Cinque Terre.
Other: This tour is appropriate for fit first time “hikers” who enjoy walking and who have good balance and who are coordinated. 
Moderate Tours: Tuscany ChiantiDordogne WalkSicily WalkLake Como Walk, and Corsica.

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.

3.91 out of 5
Ratings based on 3 Verified Reviews

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

by JMaxwell from San Ramon, CA
Posted Jul 10, 2018

Our second with Customwalks and Claire and as usual everything was great. The other guide, Dimitris was also wonderful. His joy in sharing all the wonders of his country made us feel right at home. Everything about this trip is great, the history, food, hikes, views, hotels, etc. The Greek Islands had been on our list for many years, so Thank you to Custom Walks for making another dream come true!

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.

Our second with Customwalks and Claire and as usual everything was great. The other guide, Dimitris was also wonderful. His joy in sharing all the wonders of his country made us feel right at home. Everything about this trip is great, the history, food, hikes, views, hotels, etc. The Greek Islands had been on our list for many years, so Thank you to Custom Walks for making another dream come true!
by JMaxwell from San Ramon, CA

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