Hiking tours


Greece Cyclades Island Hiking Tour

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  • Location: Greece
  • Duration: 8 Days/7 Nights (add 4 Nights for the Crete extension)
  • Departing from: Athens, Day 1
  • Tour finishes: Santorini, Day 8 (*or Chania for Crete extenxion)
  • Departures 2024: May 19 and Sept 15 as well as private departures.
  • Price 2024: Euro €3,550 per person based on double occupancy and minimum 4 people. Single Supplement Euro €480. Crete extension: €2,000 per person in double occupancy and minimum 4 people for 4 nights. Single supplement €280. 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 hikes 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 Hiking Tour Includes:

Accommodation: Accommodation in 3- and 4-star hotels: 1 night Athens, 2 nights Tinos, 2 nights Naxos, 2 nights Santorini 
Meals: 7 breakfasts, 1 lunches and 6 dinners
Luggage: Bags are transferred starting from pick-up at Athens hotel on Day 2, to final Santorini hotel
Special events: Guided visit of Acropolis including the Parthenon and Acropolis museum, tasting of local kitron liqueur, cooking lesson, visit of Akrotiri archaeological site
Transport: Private van and ferry transfers as indicated in the itinerary
Active days: 6 days of guided hiking,
Guides: At least 1 bilingual Customwalks guide accompanies departures of 2 - 8 people; 2 guides accompany departures of 9 or more people
Max group size: Tours are capped at 14 people

Booking: Please e-mail us at info@customwalks.com to receive a booking contract or simply click on the BOOK NOW button or the 'Contact Us' tab. Thanks!

    *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. 

    Greece Cyclades Island Hiking Tour itinerary Request full itinerary

    Day 1

    Arrival in Athens: transfer on your own from the Athens International airport to the Hotel Herodion (or similar) 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

    The Acropolis – ferry to Tinos. The Acropolis – ferry to Tinos. After breakfast we have a guided visit of the Acropolis, including the world famous Parthenon and the fabulous Acropolis museum. You will learn about the city's 4,000-year history and understand its importance to our world. After lunch we have a one-hour transfer to the port of Rafina where we depart for the island of Tinos by “normal” ferry (instead of the closed in Catamaran ferries) , which means you can go outside on deck to enjoy the experience of cruising along the Aegean (approx. 3.5 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 (or similar) in the heart of the old town. Overnight Tinos. The Hike: Urban walking. Hotel, breakfast and dinner included.

    Day 3

    Explore Tinos. Our hike 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. The Hike: Volax to Tinos town distance 7,7km/4.8mi, elevation gain and loss 220m/704ft and 520m/1,664ft, duration around 3 hours. Hotel, breakfast, lunch and dinner included.

    Day 4

    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 hike through the green valleys of the island, the most verdant in the entire island chain. The hike 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 (or similar). The Hike: Melanes-Chalki distance 9,5km/5.9mi, elevation gain and loss 538m/1,721ft and 359m/1,148ft, duration around 4 hours. Hotel, breakfast and dinner included.

    Day 5

    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. The Hike: Mt Zeus hike distance 6km/4mi, elevation gain and loss 419m/1,340ft and 419m/1,340ft, duration around 3 hours. Hotel, breakfast and dinner included.

    Day 6

    Transfer to Santorini and hike the crater rim. Enjoy a relaxed morning with free time to explore the labyrinthine streets of Naxos town and its Venetian built citadel before boarding the ferry to Santorini. You will not soon forget the view of Santorini’s famous cliffs from the water as we sail into the caldera. Blown apart by a massive eruption in 1500 BC, the steep volcanic cliffs are surmounted by gleaming white-washed villages. We disembark below the colorful town of Fira and then start the 3-hour hike to our hotel in Oia (pronounced “Ee-ah”). The hike is one of the most spectacular in the world, as it takes you around the rim of the island’s volcanic crater. As we hike, the sun slowly sinks toward the horizon. We will enjoy the sunsets dazzling finale from the terrace of our hotel. We then have a short walk to our restaurant for dinner together. Overnight Santorini. The Hike:  Caldera hike distance 10,7km/6.7mi, elevation gain and loss 410m/1,312ft and 512m/1,638ft, duration around 4 hours.Hotel, breakfast and dinner included.

    Day 7

    The ancient Greek city of Thira. Many people opt to have a relaxed day and simply contemplate the breathtaking view of the sea-filled caldera, punctuated by a little wander around Thira town and some shopping. For those who want to hike we take you to Pyrgos, a pretty village that was the island’s capital during medieval times. From Pyrgos the trail climbs up to the monastery of Prophet Elias. It is the highest point on the island and has commanding views. From there, we continue to the ruins of Ancient Thira, one of the oldest settlements in the Mediterranean and which is delightfully free of tourists. We descend on foot to the coast for lunch by the sea. There’s time for a swim today, so bring your bathing suit!  We reunite for a sunset drink and then dinner in lovely Oia. Overnight Santorini. The Hike: Pyrgos to Kamari hike distance 7km/4.4mi, elevation gain and loss 460m/1,472ft and 790m/2,528, duration around 4 hours. Hotel, breakfast and dinner included.

    Day 8

    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.


    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 Hotel (or similar). Hotel, breakfast and dinner included.

    Day 9

    We visit the truly wonderful Heraklion archaeological museum this morning. Recently renovated and re-curated, it features stunning artifacts from the Minoan and Mycenaean civilizations which are presented in a coherent and accessible way. Fascinating storylines (in English) make ancient history come to life. We continue with the archaeological theme as our late-morning hike takes us through the countryside to an ancient Minoan site. We stop for a delicious lunch on the vine-covered terrace of a local restaurant. After the hike, we transfer to Rethymno, one of the island's most charming towns. We walk amongst a jumble of colorfully painted Venetian-era houses, past jaunty fishing boats gently rocking in the water to a quaint taverna in the old harbor where we enjoy carafes of cold white wine and fresh seafood platters. Overnight Rethymno. Hotel, breakfast and dinner included.

    Day 10

    A late departure allows you to savor a relaxed morning and watch the village slowly come to life. Our destination today is Chania, one of the most delightful port towns in the Mediterranean. Along the way, we stop at a winery for a tasting and lunch. After checking in, you can choose to hang out in Chania or chill out on one of the superb beaches that is a short drive from town. We've left the evening "free" (dinner not included) so you can eat light and have an early night, or splash out at one of the bustling seafood restaurants along the water’s edge. 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 (or similar). Hotel and Breakfast included. Dinner not included.

    Day 11

    Our last hike takes us through the dramatic Aradaina gorge to a secluded beach whose sand gleams white with specks of marble. The hike ends at Loutros village which is only accessible by foot or by boat. We lunch by the sea and then ferry and shuttle back to Chania. Dinner together at one of the city's colorful restaurants along the curving harbor front. Overnight Chania. Overnight Chania. Hotel, breakfast and dinner included. 

    Day 12

    Depart at your leisure today. There are flights throughout the day and we may not all be leaving at the same time. Travel time in a taxi is 25 minutes to Chania airport. We are happy to organize a taxi for you. Chania airport has several flights to Athens throughout the day, as wll as direct flights to the U.K., Italy, etc. If your ideal flight is from Heraklion, you can get there with a two-hour bus or taxi ride. Breakfast included.

    Please note: Some details of the itinerary may change according to the departure date of your tour. Whenever we run a tour, we make new discoveries. Sometimes they are good discoveries, like a wonderful new trattoria, and sometimes they are bad, like a trail has been washed away. The result is that we sometimes change our itinerary to improve it by adding new wonderful elements to the tour or by removing something that does not work anymore. Rest assured, our goal is to always provide you with the best possible experience. We will advise you of any changes to the original itinerary prior to departure.  



    Activity Level 3 out of 5  = 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 hiking 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 hiking and who have good balance and who are coordinated. 
    Moderate Tours: Tuscany Chianti, Dordogne Hike, Sicily Hike, Lake Como Hike, and Corsica.
    As a point of reference, what is a 1 out 5 Activity rating? A 1 out of 5 rated tour is a tour without any hiking. Walks would be in towns, cities, and villages, and the countryside walks would be on paved, or gravel/dirt roads, and occasionally on some packed earth trails. Elevation gain and loss would be negligible.
    As a point of reference, what is a 5 out 5 Activity rating? A 5 out of 5 rated tour is a tour that would be physically challenging and technically difficult even for very fit and experienced hikers. The hikes would have steep ascents and descents on narrow, exposed trails with challenging footing, such as on scree fields, or through rock falls and boulders. Distances would be up to 25 km/16 miles per day and feature ascents of over 1,000 m/3,200 feet in a day. A 5 out of 5 tour would also mean that you would be carrying a heavier-than-normal pack. None of our tours are rated 5 out 5. Our most challenging tours are 4.5 out of 5, and they are the Dolomites Alta Via (because of some exposed trail that requires some technical expertise) and our Republic of Georgia tour which has some long hikes with over 1,000 meters of elevation gain.

    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 8 in Santorini. 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 out of 5
    Ratings based on 4 Verified Reviews

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

    by Jay H
    Posted Jun 04, 2022

    Greece and Customwalks exceeded every expectation we had for our trip. Nefeli gave us excellent background on the sites we visited, ordered delicious food at every meal, and patiently taught us many Greek words and phrases. We loved the cooking class with Nicoletta and look forward to trying her recipes.

    by JMaxwell
    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
    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
    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.

    If you have any questions or specific requests about any of our tours, we’re here to help. You can fill in the form below, send us an email, or call us and we’ll get back to you as soon as possible.

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    Italian operations office

    Greece and Customwalks exceeded every expectation we had for our trip. Nefeli gave us excellent background on the sites we visited, ordered delicious food at every meal, and patiently taught us many Greek words and phrases. We loved the cooking class with Nicoletta and look forward to trying her recipes.
    by Jay H

    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

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    Naxos harbour
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    Naxos venetian castle
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