Serifos, Sifnos and Milos in comfort: 10 self-guided days in the Cyclades

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4,6 · 20 reviews
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Sunlight on a whitewashed terrace, a first coffee facing the Aegean, and a whole day ahead to walk from village to cove at your own pace. This 10-day self-guided holiday takes you through three islands of the western Cyclades, Serifos, Sifnos and Milos, with a comfort upgrade at every stop: on each island you return in the evening to a 4-star hotel.

Kelifos knows these islands path by path. We have chosen the ferries, the addresses and the walks; a digital route guide and a GPS app lead you each morning along the old monopatia, the stone paths that link chapels, hamlets and beaches. Serifos is wild and silent, Sifnos gentle and gourmet, Milos volcanic and full of colour. You walk two to five hours a day, then swim, explore and settle at a taverna table.

Prefer small family-run hotels? The same trip exists in a charming-address version.

Itinerary

Paysage de Sifnos - Cyclades - Grèce
See interactive map

Program

Arrival at Athens airport and transfer to your hotel in Piraeus (not included, about 40 minutes; a private transfer can be booked). Check-in from about 3 pm. Depending on your arrival time, you collect your ferry tickets that evening or the next morning. A first dinner by the harbour, where the ferries set the rhythm of the town.

Accommodation3-star hotel in Piraeus

The ferry takes you to Serifos in about 2 hours (included). The island of Perseus is watched over by Chora, one of the most characterful villages of the Cyclades. You climb its narrow white lanes to the summit, where the view embraces Livadi bay, then walk back down for a first swim in crystal-clear water. A round walk.

Accommodation4-star hotel on Serifos
InfoWalking time: about 2 h
Distance5 km

A short bus ride takes you up to Chora (not included, about 10 minutes). From there, the path leads to the chapel of Stavros and through the inland villages of Kendarchos, Galani and Panagia. You can add a visit to the 16th-century monastery of Taxiarchon, where a single monk still lives among a fine collection of religious heirlooms. The return follows a beautiful monopati down to Livadi bay, where the afternoon is yours to swim and relax.

Accommodation4-star hotel on Serifos
InfoWalking time: about 5 h
Distance15 km

A short ferry crossing to Sifnos (included), the island of perched chapels, monasteries and talented potters. You settle in Kamares, on a lovely beach, for three nights. Depending on your arrival time, a first walk from Apollonia (bus not included, about 10 minutes) down to Kamares, with the sea always in view.

Accommodation4-star hotel on Sifnos
InfoWalking time: about 2 h 30
Distance7 km

Bus to Apollonia (not included, about 10 minutes). One of the loveliest walks on Sifnos crosses the island from east to west and ends at Vathy bay: a swim, the sun, a taverna terrace over the water. Return to Kamares by bus (not included, about 25 minutes).

Accommodation4-star hotel on Sifnos
InfoWalking time: about 4 h 30
Distance11 km

Bus to Kastro (not included, about 15 minutes). This walk strings together some of the island's finest places: the lanes of Kastro, the little harbour of Faros, the Chryssopighi monastery on its rock above the sea, and the beach of Platys Gialos. The monopati between Kastro and Faros is one of the most pleasant paths in the archipelago. Bus back to Kamares (not included, about 20 minutes).

Accommodation4-star hotel on Sifnos
InfoWalking time: about 3 h
Distance8 km

Ferry to Milos (about 45 minutes, included), the island of the Venus de Milo, and transfer to your hotel (included). In the afternoon, a local bus (not included) takes you to Sarakiniko and its canyon of white volcanic rock above turquoise water. In antiquity, Milos grew rich on the obsidian trade. Return by bus (not included).

Accommodation4-star hotel on Milos
InfoWalking time: about 2 h 30
Distance7 km

Transfer to Pollonia (not included, about 15 minutes from Adamas), then a small boat to Psathi, the port of Kimolos (20 to 30 minutes, ticket bought on the spot). From Chorio and its windmills lined up on the Ksaplovouni ridge, a scenic path leads to the Skiadi rock, a mushroom-shaped stone sculpted by erosion. You continue from beach to beach along the coast, with time to swim, and return to Chorio on stone-paved paths through a shaded valley and abandoned hamlets. Ferry back to Milos (about 20 to 30 minutes, not included).

Accommodation4-star hotel on Milos
InfoWalking time: about 4 h 30
Distance14 km

Depending on the ferry time, a last stroll to Klima (taxi not included), a fishing village of colourful boathouses, and a visit to the catacombs, the most important after those of Rome. Ferry to Piraeus (about 3 h 30), then transfer to Athens for the night (not included).

Accommodation3-star hotel in Athens
InfoWalking time: about 2 h 30
Distance7 km

Breakfast and check-out around 10 am. End of the trip.

The walks on each island can be done in any order, depending on the ferry schedules. Ferry times change with the season and are confirmed when your trip is booked; they may occasionally shift, and an early boat can mean missing breakfast at the hotel (some hotels then prepare a breakfast box). On 1 May the boats do not run, and the itinerary is adapted for departures spanning that date. In the rare event of strong wind, ferries stay in port and our local partners rearrange your route.

Dates, prices and booking

Participants
Price per person
Book

Price does not include

  • travel to and from Athens (flights, train, bus...)
  • airport transfers
  • drinks
  • lunches and dinners
  • printed travel pack
  • entrance fees to sites
  • personal expenses
  • tourist taxes, including environmental fees, payable locally
  • insurance
  • anything not listed under "Price includes"

2026 prices:

Price includes
  • accommodation for 9 nights in double rooms
  • 9 breakfasts
  • transfers between the port and your hotel on each island (round trip)
  • ferry tickets
  • digital travel documents
  • access to our smartphone app with GPX tracks
  • 24/7 telephone assistance during the trip
Options & supplements
  • single room supplement: +US$1,032 (low season), +US$1,185 (mid season), +US$1,226 (high season), +US$1,474 (peak season) per person
  • three travellers: by default one double room and one single room (price for 3 people plus the single room supplement); a triple room (double bed and sofa bed) is possible without discount, subject to availability
  • printed travel pack, waiting at your first hotel: US$42 per pack
  • private transfers on the islands, from your hotel to the start of the walks and back: US$714 for 2 to 4 people, US$1,321 for 5 to 8 people (to be divided between travellers)
  • private transfer from Athens airport to Piraeus: US$160 for 1 to 3 people, US$272 for 4 to 6 people
  • private transfer from central Athens to the airport: US$154 for 1 to 3 people, US$248 for 4 to 6 people
  • extra nights in Athens, on Serifos, Sifnos or Milos: on request

Your advisor

Giovanna Crippa

Giovanna Crippa

Product Manager Europe

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Practical information

On the islands you stay in 4-star hotels, in Piraeus and Athens in 3-star hotels (or equivalent comfort), always in double rooms with private bathroom. Two nights on Serifos, three on Sifnos facing the beach of Kamares, two on Milos: fewer changes, more time to enjoy each place. A single room can be booked on request.

Breakfast is served each morning at the hotel. Lunches and dinners are free: tavernas and cafés line the walks and surround every hotel, and grocery shops make a picnic easy. Sifnos, reputed as the finest table in the Cyclades, is a standing invitation to linger. Please tell us about any allergy or special diet when you book.

Two to five hours of walking a day, on well-marked paths without technical passages, with climbs of 100 to 630 m a day. The trip suits walkers in good general fitness who enjoy walking; the pace leaves room for swims, visits and long pauses on a terrace. You carry only a daypack with your essentials for the day.

Your luggage is not transported by a carrier: you take it with you on each ferry, and the transfers between port and hotel on each island are included. Travel light, with one bag per person that you can easily handle when boarding.

This is a self-guided trip, without a guide. Your digital travel documents (available in English, French and German) include access to our smartphone app for the walks and local maps (in English), the list of your hotels and your vouchers. A printed pack with maps and route guide can wait for you at your first hotel for an extra charge, on request at booking. There is no welcome meeting.

From 2 people. Solo travellers on request.

Departures on the day of your choice from mid-April to mid-October.

10 days / 9 nights / 7 to 8 days of walking.

Start on day 1 at your hotel in Piraeus (check-in around 3 pm). End on day 10 in Athens after breakfast (check-out around 10 am).

From Athens airport to Piraeus

  • By metro: line M3 (blue) to Monastiraki, then line M1 (green) to Piraeus, the terminus. About 1 hour; 6 to 10 € per person. The hotel is 800 m from the station.
  • By bus: direct line X96, about 1 h 50, 6 €. The hotel is 800 m from the stop.
  • By taxi: about 60 to 80 € per journey, or a private transfer booked with us.

From central Athens to the airport

  • By metro: from Omonia station (line M2, red, 350 m from the hotel), change at Syntagma for line M3 to the airport.
  • By bus: line X95 from Syntagma square (about 15 minutes' walk from the hotel), about 1 h 20, 6 € per person.

More ideas for Greece: our walks in the Cyclades, our holidays in Crete and our Ionian Islands escapes.

Reviews

4,6 · 20 reviews

—  These are some really beautiful hikes, but June 10–19 is a little too late in the season because of the heat. For most of the hikes, it’s impossible to set out early due to bus schedules and breakfast times at the hotels.

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