There’s no better place in the world for island hopping than Greece. Its 6,000 islands offer a lifetime of exploration, and the four that you’ll visit in the Cyclades are a good place to start. Serifos, Sifnos, Milos, and Kimolos—these charming islands will be your home during your 10-day hiking adventure. Not only are they far less crowded than some other islands in the Aegean Sea, but they also ooze an unmistakable Greek authenticity. So you’ll fill your days with daily hiking, meeting locals, tasting out-of-this-world food at typical tavernas, and strolling through flower-adorned streets, among azure-domed houses. Don’t miss out on another summer that’s not a Greek summer!
A 10-day immersion into everything Greek—that’s what this self-guided journey is all about. You will visit four islands of the sparkling Aegean Sea (Serifos, Sifnos, Milos, and Kimolos), and explore them with daily walks to the islands’ best-ofs. A great thing about this trip is that you don’t have to compromise your comfort, because you’re the one who dictates the tempo—and the accommodation, digital travel pack, breakfasts, ferry transfers, it’s all taken care of. You’ll be based in comfy hotels and switch islands at a reasonable, pleasant pace, giving you enough time to explore every one of them!
Arrive in Athens Airport, which is about an hour away from Piraeus (depending on your mode of transfer). Check into your hotel and use the rest of the day at your leisure.
Accommodation: 3-star hotel in Piraeus
Take a ferry to Serifos (takes about 2 hours), Perseus’ island, overlooked by its main village Chora—one of the most characteristic and beautiful villages of the Cyclades. Hike to the top of the village via white and narrow valleys. Once you descend down to sea level, enjoy swimming in crystal-clear waters.
Meals: Breakfast
Hiking: 5 km / 3 miles, 2 hours
Elevation: +230 m / +755 ft
Accommodation: 4-star hotel on Serifos
Hop on a bus to Chora, to the village that overlooks the bay of Livadi. Your hike starts there: discover charming chapels (such as Stavros) and villages of Kendarchos, Galani, and Panagia. You’ll also stop by the monastery of Taxiarchon from the 16th century, where a single solitary monk still lives there—you’ll also find a beautiful icon of Russian origin. Return to Chora via a wonderful monopati (Greek for path) to the bay of Livadi, where you can use the rest of the day for swimming.
Meals: Breakfast
Hiking: 15 km / 9 miles, 5 hours
Elevation: +/-630 m / +2,070 ft
Accommodation: 4-star hotel in Serifos
Ferry over to Sifnos, another spectacular island boasting numerous perched churches and monasteries. Settle in Kamares, a lovely coastal village, which will be your base for the next three nights. Depending on your arrival time, take a 10-minute bus ride from Apollonia to Kamares and squeeze in the first hike. Enjoy a pleasant downhill walk with the sea always in the backdrop.
Meals: Breakfast
Hiking: 7 km / 4.4 miles, 2.5 hours
Elevation: +270 m / +885 ft | -450 m / -1,475 ft
Accommodation: 4-star hotel on Sifnos
Today’s bus takes you on a 10-minute ride to Apollonia for one of the most beautiful walks on Sifnos! Crossing the island from east to west, the walk ends on the beach of Vathi, where you can swim in its azure seas or rest in a tavern. Once you’re rested from the walk, hop on a bus back to Kamares (around 25 minutes).
Meals: Breakfast
Hiking: 11 km / 6.8 miles, 2.5 hours
Elevation: +490 m / +1,610 ft | -670 m / -2,200 ft
Accommodation: 4-star hotel on Sifnos
Take a 15-minute local bus ride to Kastro. Once there, today’s hike through some of the most charming spots of Sifnos begins! After strolling through the serene streets of Kastro, continue to the wonderful port of Faros and then onto Chrisopigi—an iconic monastery perched atop a rock. A little further on, you’ll reach Platys Gialos, a spectacular sandy beach. Take a bus back to Kamares.
Meals: Breakfast
Hiking: 8 km / 5 miles, 3 hours
Elevation: +/-210 m / +690 ft
Accommodation: 4-star hotel on Sifnos
Island change! Hop on a ferry journey lasting approximately 45 minutes to reach the captivating island of Milos, forever linked with the renowned Venus. Discover the mesmerizing Sarakiniko white canyon, boasting crystalline waters that invite exploration. Milos was once one of the most famous islands for obsidian trade in ancient times.
Meals: Breakfast
Hiking: 7 km / 4.4 miles, 2.5 hours
Elevation: +80 m / +265 ft | -60 m / -200 ft
Accommodation: 4-star hotel on Milos
Transfer to Pollonia on the island and then hop on a boat. It will take you 20-30 minutes to reach Psathi, port of the island Kimolos. This picturesque island is of volcanic origin and will win you over with its serenity. Leave for Chorio, the main town on the island with its mills lined up on the Ksaplovouni ridge. Continue walking to reach the Skiadi rock, an incredible, otherworldly mushroom-shaped rock, followed by continuing onto the seaside. Use the time at the beach to relax, and then return to Chorio via its wonderful paths in a shaded valley, passing by several old hamlets. Ferry back to Milos.
Meals: Breakfast
Hiking: 14 km / 9 miles, 4.5 hours
Elevation: +/-350 m / +1,150 ft
Accommodation: 4-star hotel on Milos
Squeeze in your last hike to Klima, a charming fishing village on the island, and visit the catacombs (the most famous ones after Rome). Take a ferry back to Piraeus (around 3.5 hours) and spend your last night of the trip in Athens.
Meals: Breakfast
Hiking: 7 km / 9 miles, 2.5 hours
Elevation: +320 m / +1,050 ft | -160 m / -525 ft
Accommodation: 3-star hotel in Athens
Today is the last day of this wonderful adventure! After a hearty breakfast, pack up and head home (or keep on exploring!).
Meals: Breakfast
I really appreciated Grand Angle, a warm, smiling team and above all really attentive to my desires. This is the ideal place to find the trip that suits everyone, I recommend! 🙂
Super team of professionals, very responsive and who know how to advise us and make us live beautiful stays!
Included:
Add-ons (can be added at checkout):
Not included:
*Morning departures of boats may prevent you from having breakfasts in your hotels. If that happens, you will not be refunded. However, some hotels prepare “breakfast boxes” in case of an early departure. Make sure to discuss this at the reception in time.
No hiking experience is necessary in order to join this self-guided hiking tour in the Greek Cyclades. This is a beginner-friendly adventure, but you still need to be in good shape to walk 2-5 hours a day. If you have a little one who’d love an active vacation, bring them along! This adventure is family-friendly and you can take your time — with as many breaks as you need.
Ascents vary from 100 to 650 m per day (330-2,130 ft). Keep in mind that you’ll be carrying a daypack with things you might need throughout the day, but a great thing about this tour is that you get to do it at your own pace!
Here’s a list of clothing we suggest you bring:
Here’s a list of other personal items we suggest you 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.
During the day, all you’ll have to carry is a light daypack with things you might need throughout the day. When you’re transferring to another island, you will have to carry it yourself to/from the airport and on the ferries.
You’ll travel from one island to the next on regular ferries that cross the Aegean Sea from Piraeus. Your guiding company will provide you with the most up-to-date schedule, but it’s recommended you check the ferry schedule beforehand and make sure you get to the port on time. It’s interesting that Greek ferries can navigate until gale-force 9 winds (which is a lot), but if the wind is even stronger, they must remain in port. Still, you will have telephone assistance during the trip and your guiding company will make necessary arrangements.
To get to your day hikes, you will use public transport and city lines (not included in the price of the tour).
You can also opt for private transfers on the islands (can be added at checkout), when you’re getting to and from the hiking sites on Serifos, Sifnos, and Milos. By choosing this option, you don’t have to rely on local buses. This is a list of organized private transfers:
Group sizes and prices:
Hiking in the Greek Cyclades 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.
To get to Piraeus, the starting point of your hiking adventure in the Greek Cyclades, it’s best to fly into Athens International Airport (ATH). From there, you can take a train or a bus to Piraeus, which takes up to 1.5 hours. It’s also possible for your guiding company to arrange a private transfer (about a 40-minute ride), just let us know in time.
Once you get to Piraeus, check into your hotel.
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!
Deposits
Secure your spot with a 30% deposit upon booking! The remaining 70% of the trip price must be paid 90 days prior to departure at the latest. If booking within 90 days of departure, the full amount is required at the time of booking.
Cancellations
Booking fees are non-refundable after a 48-hour grace period. During checkout, however, you can choose one of 57hours’ flexibility options—Basic, Flexible, or Super Flexible. Depending on which one you choose, a different cancellation policy will apply to your booking.
Basic
Flexible
Super Flexible
