If you’ve been searching for a wildly underrated hiking destination, the islands of the Western Cyclades might be your next holiday spot. Over the course of 10 days, we’ll explore the unspoiled landscapes of Sifnos, Milos, and Kimolos. We’ll visit charming whitewashed villages, trek along dramatic coastlines with breathtaking views of the Aegean, and discover secluded beaches together. Each island offers something unique: from the lush valleys of Sifnos and the otherworldly volcanic terrain of Milos, to the beautiful coves and beaches of Kimolos. Incredible hikes aside, we’ll also get to enjoy delicious food at local tavernas and mingle with friendly locals. If all goes well, we might even break a few plates, just as the Greeks do. Opa!
Discover 3 unspoiled islands of the Western Cyclades on this hiking holiday. Explore secluded beaches, forgotten valleys, hidden paths, amazing views, and picturesque villages during 10 exciting days. You’ll stay in 4- and 5-star hotels, eat and drink in local tavernas, and swim on beautiful Greek beaches, all with the help of an experienced guide. All transfers and ferry tickets are taken care of, so all you need to do is pack your bags and enjoy the charm of Sifnos, Milos, and Kimolos.
After the arrival in Athens airport, you’re going to be transferred to your hotel in Piraeus, a large and bustling port city that’s an integral part of Athens. At the hotel, you’ll have a meet-and-greet with your experienced guide, and then we’re off to a nice dinner and a restful night in our cozy rooms.
Meals: Dinner
Accommodation: Hotel in Piraeus
The adventure may begin! We’ll take a ferry to Sifnos (approx. 2h30), a Cycladic island where traditional villages and 370 churches and chapels are perched high above amazing coastal scenery. We’ll settle in Kamares, in front of a beautiful beach where we’ll swim and have a picnic with fresh local produce. Later on, we’re transferring to Kastro, where a scenic path takes us on our first easy hike, south to the village of Faros and its picturesque harbor. A bit further is the monastery of Panagia Chryssopigi, built on a piece of land jutting out into the sea.
The day ends with a transfer back to Kamares, but there’s also an option to continue inland to Apollonia along the irrigation channels to the monastery of Vryssi and the village of Exampela, which is the birthplace of the famous chef and food writer of the first half of the 20th century, Nikolaos Tselementes.
Meals: Breakfast, lunch, and dinner
Short stage hiking: 6 km / 3.7 miles (approx. 2h30min)
Long stage hiking: 12 km / 7.45 miles (4h)
Short stage elevation: +195 m / +640 ft, -210 m / -689 ft
Long stage elevation: +465 m / +1,525 ft, -285 m / -935 ft
Accommodation: Hotel in Sifnos
On Day 3, we’re going to take a short transfer to Apollonia, and then head south to hike along a pretty route dotted with numerous chapels. Once in Katavati village, we’ll climb Mount Profitis Ilias, the highest point on the island with its imposing 12th-century monastery. What follows is a descent to Vougnous cave and the springs of Kalamitsi before arriving in Vathy bay. Once we’ve seen all these amazing views, it’s time to head back to Kamares.
Meals: Breakfast, lunch, and dinner
Hiking: 10 km / 6.2 miles (approx. 5 hours)
Elevation: +470 m / +1,542 ft, -660 m / -2,165 ft
Accommodation: Hotel in Sifnos
The day begins with a short transfer to Apollonia, and then we’re hiking through beautiful paths that lead us to Artemónas and its charming cobbled streets. Next up, the famous chapel of Panaghia Poulati, located high above the sea. We’ll continue along the coast to Kastro, the island’s ancient fortified capital with stunning views overlooking the sea, and then a climb back to Kato Petali village awaits. After that, we’ll return to Apollonia, and then back to Kamares for some much-needed rest and relaxation in our hotel.
Meals: Breakfast, lunch, and dinner
Hiking: About 3h45 of walking
Elevation: +250 m / +820 ft, -250 m / -820 ft
Accommodation: Hotel in Sifnos
Our fifth day is reserved for an amazing looping stage with a change of scenery. We’ll transfer to Platis Gialos, and hike among olive trees until we come across the abandoned farm of Moussia. Further on, the colors of volcanic rocks will leave us mesmerized, while a small islet of Kitriani will reveal the oldest chapel on Sifnos. Then, it’s Platis Gialos back again, with a nice descent that offers a glorious view of the bay. We’ll take some time to swim and enjoy everything this superb beach has to offer. After that, we’ll transfer back to Kamares.
Meals: Breakfast, lunch, and dinner
Hiking: 11 km / 6.8 miles, about 4 hours of walking
Elevation: +435 m / +1,427 ft, -435 m / -1,427 ft
Accommodation: Hotel in Sifnos
We’ll kick off the day with a hearty breakfast, and then leave Sifnos by ferry for the island of Milos. After checking into our hotel in Adamas, we’ll transfer to the outskirts of Fylakopi, which is the starting point for our hike. This day will be filled with amazing views: we’ll hike along the coast to Sarakiniko, with volcanic and sedimentary rocks on the side, then we’ll pass the Papafraga cave with its transparent waters, and in the end we’ll pass the small natural harbors of Pachena and Mytakas before the picturesque port of Mandrakia.
Meals: Breakfast, lunch, and dinner
Hiking: About 4h15 of walking
Elevation: +220 m / +722 ft, -220 m / -722 ft
Accommodation: Hotel in Milos
On day 7, we’ll cross from Pollonia to Psathi, port of the island of Kimolos, an astounding volcanic island close to Milos. We’ll hike to Chorio, the main town with its traditional windmills lined on the Ksaplovouni ridge. After that, we’ll follow a scenic route to Skiadi Rock, an interesting mushroom-shaped rock sculpted by erosion. Once we reach the seafront, it’s time for swimming and leisure. On our way back to Chorio, we’ll walk on gravel paths through a pretty shaded valley, and pass through several ruined hamlets. Later on, we’re crossing back to Milos for a nice dinner and some rest.
Meals: Breakfast, lunch, and dinner
Hiking: About 5 hours of walking
Elevation: +300 m / +984 ft, -300 m / -984 ft
Accommodation: Hotel in Milos
The eighth day of our hiking trip begins by walking along paths with breathtaking views. The first stop is the fishing village of Klima with its colorful houses painted in blue, red, yellow, and green. We’ll walk to the nearby catacombs, and then we’ll go to Plaka, with its cobbled streets, white houses, and a church with a rounded dome. Later on, it’s back to Adamas.
Meals: Breakfast, lunch, and dinner
Hiking: About 3h30 of walking
Elevation: +250 m / +820 ft, -120 m / -394 m
Accommodation: Hotel in Milos
On Day 9, we’ll take the ferry to the port of Piraeus. The trip will take about 3 hours. Once we arrive, a private transfer to Athens awaits, where we’ll eat local dishes and spend the night in a hotel.
Meals: Breakfast, lunch, and dinner
Accommodation: Hotel in Athens
Day 10 marks the final day of our hiking trip. After breakfast, we’ll transfer to the Athens airport. Alternatively, if you’d like to stay longer and explore the area, your guides are happy to give you recommendations!
Meals: Breakfast
I really appreciated Grand Angle, a warm, smiling team and above all really attentive to my desires. It’s the ideal place to find the trip that suits everyone, I recommend! 🙂
If you want fresh air, adrenaline and great encounters… (the landscapes 😉 …) you are 100% in the right place!!
What you get on this adventure:
What’s not included:
In order to join this Western Cyclades hiking holiday, you need to enjoy walking and be in good shape. There’s 2 to 5 hours of walking per day. The difference in altitude varies, between 100 and 720m (maximum) per day.
All you need to carry is a small backpack with your day’s essentials, a picnic lunch and food for the day. You will have to transfer all your luggage from the boat to the vehicle that transports luggage to the islands, and then to your room (and vice versa).
Here’s a list of the equipment you need to bring:
Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.
Group sizes and pricing
Western Cyclades hiking holidays can be arranged for larger groups. Contact us to make arrangements.
Min. age requirements
If your group has hikers under the age of 18, contact us prior to booking to make arrangements.
The climate of the islands is Mediterranean, meaning hot and dry in summer and mild and rainy in winter, but with significant differences between regions and archipelagos. The Cyclades regularly suffer from a lack of rain, and during the summer season, which here lasts almost 6 months, there is little or no rainfall from late May to early October. The Cyclades also enjoy relatively cool summers (for Greece) thanks to the famous ‘Meltem’, a seasonal wind that pleasantly refreshes the atmosphere during the summer months, but which sometimes gets so strong that boats are immobilized in port for a few hours.
The average temperature on the Cyclades ranges from around 11/12 °C (52/53 °F) in January and February to around 26 °C (79 °F) in July and August.
You’ll be traveling from island to island on regular ferries from Piraeus. These big boats are a guarantee of arrival on the islands. Greek ferries can sail at up to force 9/10, depending on their size. There can be a lot of wind at sea without you even realizing its effects on the islands. You just need to be in a sheltered cove or bay (or on the right side of the island) not to feel the effects.
Please note that in the Mediterranean, the weather can change, and boats can be delayed. We adapt to the circumstances. All boat timetables are subject to change.
The starting point of your Western Cyclades Hiking Tour is Athens. To get there, most people fly into Athens International Airport (AIA). From there, a transfer to a hotel in Piraeus awaits (all transfers are included in this trip).
Once you’re there, you will meet your guide. The exact time and place, along with the name and contact details of the guide, will be provided before departure.
We highly recommend that you cover all your bases with both medical and travel protection. To make your booking and traveling experience as carefree as possible, simply choose Redpoint—the official 57hours insurance partner!
Redpoint tailors their protection packages for adventure travel, offering a comprehensive travel program, even in remote locations. Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.
Once your booking is confirmed and your trip is paid in full, you will be offered to purchase Redpoint’s protection. If you need any help or require more information, let us know and we will be happy to help!
If you are a national of a country that does not have a visa waiver agreement with the
European Union, you must obtain a Schengen visa before traveling to Greece. The Schengen visa allows you to stay for up to 90 days within a 180-day period in the Schengen area, of which Greece is a part.
Please note that travel insurance is compulsory to obtain a Schengen visa. It must cover medical expenses, hospitalization and repatriation in the event of illness or accident, with a minimum cover of €30,000.
Deposits
You can secure one of the set dates with a 30% deposit upon booking. The remaining 70% of the trip price is to be paid 90 days prior to departure, at the latest.
Cancellations
Booking fees are non-refundable in all cases. During checkout, however, you can choose one of 57hours’ flexibility options:
Basic
Flexible
Super Flexible
Very well organized, very competent and friendly stuff and it was a great Bike Holiday!