There was an error with your log in

Greece possesses this unique energy that few places in the world can match. Flower-adorned streets, azure-domed houses, lavender-infused air, whitewashed villages, turquoise seas, fragrant Mediterranean herbs… It’s a true feast for all senses—and you’ll get to experience all that over the course of this 10-day hiking adventure in the Greek Cyclades. This historic archipelago consists of over 200 islands in the sparkling Aegean Sea, and you’ll be visiting four of them: Serifos, Sifnos, Milos & Kimolos. Though they’re not as popular as some of their peers (looking at you, Santorini), they’re just as beautiful and, lucky for you, less crowded — providing guests with authentic and traditional experiences. This is island hopping at its finest. Ready for a summer vacay in Greece?

Book a call

Adventure highlights

  • Greek food odyssey

    Moussaka, gyros, tzatziki, choriatiki… You’ll soon realize why Greece makes an appearance on every foodie’s bucket list

  • Explore Serifos, Sifnos, Milos & Kimolos on foot

    Soak in the authentic Greek culture on less-crowded islands and mingle with the locals

  • “Wow” will become your most-used word

    Daily hikes will take you to cliff-perched monastery, massive mushroom-shaped rock, and bone-white moon-looking beach


A Greek getaway is sometimes all you need. Well, this is more than just a short getaway—this is a 10-day total immersion into everything Greek in the Cyclades. As a part of this hiking adventure, you’ll enjoy daily walks to the islands’ best-ofs and use every opportunity to enjoy the sparkling warm seas! Local ferries will take you to four Greek islands—Serifos, Sifnos, Milos & Kimolos—and explore their charms. 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 meet your guide and your group at 6 pm. You’ll have an orientation meeting where you’ll discuss the itinerary and the plan, after which you’ll go for your first group dinner.

    Accommodation: 3* Hotel in Piraeus
    Meals: Dinner

    Piraeus port city
  • 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. Get back to Serifos and have dinner.

    Meals: Breakfast, lunch, and dinner
    Distance: 5 km / 3 miles
    Accommodation: 3* Hotel in Serifos
    Hiking time: 2 hours
    Elevation: +250 m / +820 ft

    Chora in Serifos, Greece
  • 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. Once you return to Serifos, enjoy dinner with your group.

    Meals:Breakfast, lunch, and dinner
    15 km / 9 miles
    Accommodation: 3* Hotel in Serifos
    Hiking time: 5 hours
    Elevation: +610 m / +2,000 ft | -600 m / -2,000 ft

    Serifos, Livadi
  • 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. Get back to Kamares and have dinner.

    Meals: Breakfast, lunch, and dinner
    Distance: 5 km / 3 miles
    Accommodation: 3* Hotel in Sifnos
    Hiking time: 2 hours
    Elevation: +10 m / +33 ft | -190 m / -623 ft

    Kamares beach 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). Dinner will be in Kamares.

    Meals: Breakfast, lunch, and dinner
    Distance: 10 km / 6 miles
    Accommodation: 3* Hotel in Sifnos
    Hiking time: 4.5 hours
    Elevation: +470 m / +1,542 ft | -660 m / -2,165 ft

    Apollonia Sifnos Greece
  • 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 and go out for dinner.

    Meals: Breakfast, lunch, and dinner
    Distance: 8 km / 5 miles
    Accommodation: 3* Hotel in Sifnos
    Hiking time: 4 hours
    Elevation: +250 m / +820 ft | -250 m / -820 ft

    Chrisopigi monastery
  • 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. Dinner will be in Adamantas.

    Meals: Breakfast, lunch, and dinner
    Distance: 7 km / 4 miles
    Accommodation: 2* Hotel in Milos
    Hiking time: 3.5 hours
    Elevation: +110 m / +360 ft | -1,000 m / -3,280 ft

    Sarakiniko beach
  • 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, and go to Adamantas for dinner.

    Meals: Breakfast, lunch, and dinner
    Distance: 14 km / 9 miles
    Accommodation: 2* Hotel in Milos
    Hiking time: 3.5 hours
    Elevation: +300 m / +985 ft | -300 m / -985 ft

    Skiadi rock, Kimolos
  • 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. You’ll meet your group for your final dinner.

    Meals: Breakfast, lunch, and dinner
    Distance: 7 km / 9 miles
    Accommodation: 3* Hotel in Athens
    Hiking time: 3.5 hours
    Elevation: +300 m / +985 ft | -160 m / -525 ft

    Milos, Klima
  • Today is the last day of this wonderful adventure! Say goodbye to your guide and your team. If you’d like to stay longer and continue exploring Greece, just ask your guide for some recommendations!

    Meals: Breakfast

    Athens in Greece
Get free trip brochure
Download Hiking in the Cyclades: Greek Island-Hopping Paradise Brochure
The brochure contains:
Adventure and location overview, itinerary, available dates, what's included, how to prepare, and much more.
Brochure sent, check your inbox
Talk with us and let one of our adventure experts help you plan your perfect adventure.

Meet your guide

Grand Angle
Grand Angle
Grand Angle was born in 1983, when its founders Jean-Claude and Anne-Marie wanted to professionally do what they enjoy the most in life—spend time in the great outdoors. Today Grand Angle has grown into a tour operator with a great team of guides and in-office experts offering trips throughout Europe. Hiking or biking, on snow or by the sea, luxury or cultural, Grand Angle has it all!
5.00 (4 reviews)
Anais Bouffard (source: Google Reviews)

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! 🙂

Camille Arres (source: Google Reviews)

Super team of professionals, very responsive and who know how to advise us and make us live beautiful stays!

Rebecca Evans (source: Google Reviews)

If you want fresh air, adrenaline and beautiful encounters… (the landscapes;) …) you are 100% in the right place!!

Bertrand Decoux (source: Google Reviews)

Thank you to the whole team, very professional! Excellent service before + during our stay. we recommend!

Things to know

  • What you get on this adventure:

      • 10-day guided hiking adventure in the Greek Cyclades
      • Accommodation (9 nights in double or twin room)
      • All meals (detailed in the itinerary — lunches will be picnics on the trail)
      • Transfers during the tour
        • Boat and ferry tickets
        • All transfers from port to accommodations
        • All transfers to/from hikes

    What’s not included:

      • Transportation to Greece
      • Drinks
      • Personal expenses
      • Tourist tax (must be paid on the spot)
      • Cost of extra museum and/or attraction site visits
      • Insurance
      • Everything not under the “what’s included”
      • Single room supplement — available upon request
      • Transfers from Athens Airport to Piraeus or to the airport — available upon request

    Please let us know if you have allergies or dietary requirements—your guides will do their best to adapt your meals.

  • No hiking experience is necessary in order to join this 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. 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.

  • Here’s a list of clothing we suggest you bring:

      • Hiking clothing
        • Hiking socks
        • Fleece jacket
        • Hiking trousers (quick-drying)
        • Technical shorts & t.shirt
        • Underwear (quick-drying)
        • Long-sleeved shirt (quick-drying)
      • Good quality waterproof walking boots (with a moulded sole & deep tread which provide good ankle support)
      • Another pair of shoes for the evenings
      • Leisure clothing for the evenings
      • Bathing suit
      • Rain jacket or an umbrella

    Here’s a list of other personal items we suggest you bring:

      • Luggage for all your things (backpack, travel bag, or suitcase) — 20 kg maximum
      • Day pack large enough to carry your personal belongings, water, and picnic during the day (from 30L)
      • Hiking poles — optional, but recommended
      • Picnic lunches — bowl, box, or plate & cutlery
      • Water bottle or hydration bladder (2L capacity)
      • High SPF sunscreen & lip balm
      • Sunglasses
      • Sunhat
      • Clothing for hiking & leisure time
      • Toiletries (hand sanitizer, bug spray, toilet paper, etc.)
      • Camera — optional (but recommended)

    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. Though departure times may change, your guide will check the schedule and make sure you’re 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, your guide will always be in touch with the local partners and they’ll do their best to re-organize your tour.

    To get to your day hikes, your group and your guide will use public transport and city lines.

  • Group sizes and prices:

      • For this guided adventure in the Greek Cyclades, the maximum group size is 13 people with one to two guides.
      • It takes a minimum of 3 people for this tour to operate. The cost per person decreases as the group grows, so it’s the perfect opportunity to hike with friends and family!
      • Please keep in mind that the departure cannot be confirmed until your guides receive confirmations for their lodging partners.

    Hiking in the Greek Cyclades can be arranged for larger groups. Contact us to make arrangements.

    Min. age requirements:

      • If you are older than 18, you’re good to go.
      • Minors younger than 18 may be permitted to join the hike on a case-by-case basis, but must be in the presence of a parent or legal guardian.

    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 guides 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 where you’ll most likely meet your guide.

  • 57hours is committed to providing safe outdoor adventure experiences. We require all guides using our platform to have a COVID-19 safety plan and to make the details of that plan accessible to travelers. In most cases, group sizes will be reduced, guides will avoid overcrowded locations, and other safety measures will be met depending on the location and activity.

    We also expect clients to respect local regulations and take measures to protect themselves, their guides, and the communities they’re traveling to. For more information on COVID-19 measures in Greece, please refer to the COVID-19 travel advice for Greece.

    Please contact us if you have any questions or require further information. We are happy to provide you with the most up-to-date information!

  • 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.

    Secure your early bird spot with a 10% deposit! This tour gets sold out very quickly, but with early-bird booking, you will be the first one to know about any new upcoming dates. Pick your preferred dates without the risk of your bucket list adventure selling out!

    • Only 10% of the total amount should be paid as a deposit upon booking. This deposit is non-refundable, but can be transferred to another 57hours adventure anytime in case the dates don’t suit you.
    • Once the dates are set, you can confirm your booking by paying another 20% of the total amount.
    • The final balance is due 3 months (90 days) prior to departure.


    Booking fees are non-refundable in all cases. During checkout, however, you can choose one of 57hours’ flexibility options:


    • In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
    • For cancellations 60 or more days before the trip, you are eligible for a 70% refund of the trip price.
    • For cancellations 0-59 days before the trip, there is no refund.


    • In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
    • For cancellations 60 or more days before the trip, you are eligible for a full refund of the trip price.
    • For cancellations 30-59 days before the trip, you are eligible for a 50% refund of the trip price.
    • For cancellations 0-29 days before the trip, there is no refund.

    Super Flexible

    • In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
    • For cancellations 30 or more days before the trip, you are eligible for a full refund of the trip price.
    • For cancellations 0-29 days before the trip, you are eligible for a 50% refund of the trip price.
Have more questions? Read our FAQ, or Talk with us
From $3,020 ()
/ 10 days
Saved to bucket list
Removed from bucket list

Choose a currency

  • USD - $
    US Dollar
  • EUR - €
  • AUD - AU$
    Australian Dollar
  • CAD - CA$
    Canadian Dollar
  • GBP - £
    British Pound Sterling
  • CHF - CHF
    Swiss Franc
  • JPY - ¥
    Japanese Yen
  • SGD - S$
    Singapore Dollar
  • HKD - HK$
    Hong Kong Dollar
  • DKK - Dkr
    Danish Krone
  • NOK - Nkr
    Norwegian Krone
  • SEK - Skr
    Swedish Krona