Self-Guided Hiking in Greece: Island Hopping in the Cyclades

What you get on this adventure:

• • 10-day self-guided hiking adventure in the Greek Cyclades
  • Accommodation (9 nights in double or twin room)*
  • Breakfasts from Day 2 to Day 10**
  • Digital travel pack (necessary documents for the trip + access to the guide’s app and maps)
  • Transfers during the tour (ferries & to and from the port—except on Milos, since the hotel is near the port)
    • Ferry tickets
    • Round-trip transfer from the port of Serifos to the hotel in Serifos
    • Round-trip transfer from the port of Sifnos to the hotel in Sifnos
  • Telephone assistance during the trip

What’s not included:

• • Transportation to Greece
  • Drinks
  • Printed roadbook and maps — available at an additional cost upon booking
  • Lunches and dinners
  • Any transfers not mention in the “what’s included”
  • Personal expenses
  • Tourist tax (must be paid on the spot)
  • Insurance
  • Everything not under the “what’s included”
  • Single room supplement — available at an additional cost
  • Option of private transfers on the islands — available upon request, more info below
  • Transfers from Athens Airport to Piraeus or to the airport — available upon request

*Please note that accommodations are subject to availability and it may not be possible to book the exact accommodations listed day-by-day in the itinerary (in case there is a detailed list). In case rooms are no longer available, dormitory accommodation might be booked instead.

**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.

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

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:

• • 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. 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, 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:

• • Serifos Island
    • Livadi — Chora
  • Sifnos Island
    • Day 4: Kamares — Apollonia
    • Day 5: Kamares — Apollonia / Vathy — Kamares
    • Day 6: Kamares — Kastro / Platys Gialos — Kamares
  • Milos Island
    • Day 7: Adamas — Fylakopi / Sarakiniko — Adamas
    • Day 8: Adamas to Pollonia (round trip)
    • Day 9: Plaka — Adamas

Let us know if you’re interested in private transfers on the islands. The price varies depending on the number of people.

Group sizes and prices:

• • For this self-guided adventure in the Greek Cyclades, it takes a minimum of 2 persons for this tour to run. The maximum group size is set at 8.
  • 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. If the guide is unable to secure your preferred dates/accommodation, you’ll get a full refund!

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 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 emergency medical and travel insurance. With medical insurance, if you have an accident or medical emergency on or off the mountain, you’ll avoid paying out of pocket for costly expenses. This covers everything from hospital treatments to emergency air transportation and more.

Travel insurance covers canceled flights, natural disasters and other scenarios that may interrupt your travel plans.

We also expect you to respect local regulations and take measures to protect yourselves, your guides, and the communities you’re traveling to.

If you need assistance selecting the right insurance for your group, let us know and we will be happy to help!