The Enchanting Cyclades

Aphrodite, brilliant sunlight & sparkling sea
Begin your self-guided, three-island walk with a stay in eclectic Athens, followed by days of leisurely island-hopping to explore churches and a castle on Serifos, beaches and bays on Sifnos and surreal white landscapes on Milos.
The Enchanting Cyclades. 11 nights
The Enchanting Cyclades. 11 nights

Holiday information


​A walking holiday in the Cyclades

The Cyclades are one of the most popular and fascinating island groups in the Aegean, set in a circle around the sacred island of Delos. The islands are the peaks of a long-submerged mountain range, including two extinct volcanoes, Santorini and Milos, and are famed for their cubic architecture and wonderful beaches. Although easily accessible from the Greek mainland, a quiet traditional way of life has been preserved on many of the islands, and the warmest of welcomes awaits the traveller.
From the classical splendour of Athens sail south to discover the picturesque white villages and undulating hills of Serifos; the terraced hillsides and cobbled lanes of Sifnos; and the dramatic white pumice cliffs of Milos, where the Venus (or Aphrodite) de Milo statue was discovered, on an island-hopping adventure that reveals three of the lesser-known islands of the archipelago.


The key to Inntravel holidays is flexibility. Subject to the ferry timetable, you can start on the day of your choice, and are free to add extra nights.
  • The average maximum daytime temperatures and monthly rainfall relate to the nearest weather station and are intended as a guide only.

    The best time for flowers is April and May.
    Average temperatures and rainfall
      Jan Feb Mar Apr May Jun Jul Aug Sep Oct Nov Dec
    °C 14 14 15 19 23 27 29 28 26 22 18 15
    mm 90 62 56 25 13 4 1 1 10 54 67 87
  • Arrival in Athens
    Night 1: at Philippos or Herodion Hotel (where you spend two nights).
    As your first night’s accommodation is on the day of travel, Day 1 is your first day of exploration.
  • Day in Athens
    Today you have a full day to explore the fascinating Greek capital and its wealth of classical ruins. If you've never been to Athens before, you'll no doubt want to visit the Parthenon. Other key sights include Hadrian’s Arch and Panathenaikon, a replica of the ancient Athenian Olympic stadium, made entirely of the same white marble as the Parthenon.

    You can also use our self-guided walking tour to guide you through the streets to the district of Plaka, a lively and narrow pedestrianised road, lined with restaurants on one side and stallholders peddling their wares on the other.

    For something different, you might like to take the funicular to the top of Lykavitos Hill to see the city and mountains beyond from a different perspective.
  • Travel to Serifos
    After taking the metro (30 mins) to the port of Piraeus, you catch the ferry (2h30) for the island of Serifos (pay locally for all ferries on this holiday). The arrival by boat is considered to be the most beautiful approach to an island capital anywhere. Your three nights on the island are spent at the Aigaion Apartments or Galazio Suites.
  • Choice of routes on Serifos: 6km to 10km
    Serifos, with its landscape of wide sandy beaches, gently rolling hills and its small picturesque capital topped by white, domed churches and the remains of an ancient fortress overlooking the sea, is untouched by mass tourism. We suggest three walks, two of which are accessed by bus (pay locally).

    There-and-back walk to Chora's castle: 6km, 2.5hrs; ascent/descent 285m
    This short walk explores Chora, the island's capital, taking you to its ruined hill-top kastro. Not much of the medieval castle remains, but the views are superb,  stretching over the bay of Livadi, the tree-less landscape of Serifos and towards the island of Sifnos.

    The Empty North: 10km, 4hrs; ascent 525m/descent 505m
    The second walk takes you to the uninhabited north. The huge number of terrace walls and mule paths that meander through this rocky landscape demonstrate how much time and energy has gone into the cultivation of this land in the past. The lack of trees makes for clear views northwards and towards several islands. You pass through three tiny villages to reach the monastery at Taxiarchon, looked after by one monk. Return from here by bus.

    The Hills of Kallitsós: 6km, 2.5hrs; ascent 310m/descent 330m; longer version 11km, 3hrs
    Take a bus or taxi to Taxiarchon monastery. From here you follow an enchanting old kalderimi in the hills above the small village of Kalitsos on the island’s north eastern coast, enjoying some of the island's finest views as you continue to Pano Chora. From here, you can return to your hotel by bus, taxi or on foot. This walk can be combined with the Empty North walk.
    Chora's Castle walk: 3km each way
    En route to Chora's castle
    The Empty North walk: 10km
    The Hills of Kalitsos: 6km
  • Travel to Sifnos
    You take the boat (pay locally) for the 30-minute crossing to Sifnos, a beautiful, hilly island with white, flat-roofed houses glinting in the bright sunshine among terraces of olive trees, brilliant fuchsias and bougainvilleas. Your three nights on Sifnos are spent at the Hotel Delfini or Nymphs Hotel. If you have time on arrival, you could head out on a walk (see Days 6-7).
  • Choice of routes on Sifnos: 8km or 9km
    We provide notes for a choice of walks here (accessed by bus or taxi, pay locally).

    Circular walk from Apollonia to Kastro: 9km, 3.5hrs; ascent/descent 420m
    On this walk you will be introduced to the beautiful cultivated landscape of Sifnos: dry stone walls and cobbled footpaths wind across the terraced slopes; dovecotes and cube-shaped houses emerge from the green vineyards and olive groves; high above all of this a few bright white monasteries adorn the bare mountain tops. Your destination is Kastro, a good example of a medieval fortified village.

    From Apollonia to Faros Bay: 8km, 3hrs; ascent 175m/descent 365m
    Paths lead to the south coast through abandoned fields and terraces, where two surprisingly beautiful bays, including Faros, form a friendly welcome after quite a steep descent. You could visit Chrisopighi monastery before returning to your hotel.

    From Apollonia to Vathy Bay: 9km, 3.5hrs; ascent 290m/descent 470m
    This walk takes you deep into the interior of Sifnos. Vathy literally means ‘deep’ and the eponymous bay lies far and deep in the most desolate part of the island. You can walk there directly, or make a detour to the summit of Ayios Andreas, home to an important archaeological site. The climb to the top is rewarded by wonderful views across this beautiful island and the surrounding Cyclades.
    Apollonia to Kastro: 9km
    Kastro walk
    Apollonia to Faros Bay: 8km
    Apollonia to Vathy Bay: 9km
  • Travel to Milos
    You leave Sifnos by boat bound for the harbour town of Adamas, one hour away on Milos, whose multi-coloured volcanic landscapes give the island a distinctive feel. Your base for your final three nights is the Villa Notos or the Thalassitra Village Hotel.
  • Choice of routes on Milos: 11km or 12km
    On Milos, inviting paths lead along sandy beaches to secluded bays with panoramic views over the glittering sea. We provide notes for two walks.

    Circular walk to Plaka: 11km, 4.5hrs; ascent/descent 490m
    The focus of this walk is Plaka, the traditional capital of Milos. Following a little-used kalderimi, you climb into the hills where the ancient city was once located. Explore the alleys of medieval Plaka and reach the summit to enjoy views across the bay. Continue past the ancient theatre and the early Christian catacombs to the extraordinary port town of Klima before descending back to Adamas.

    From Phylakopi to Adamas: 12km, 4hrs; ascent/descent 210m
    This mostly level walk starts at Phylakopi (accessed by bus or taxi; pay locally), one of the most important sites of settlement in prehistoric Greece, now left to the elements. The route passes extraordinary geological phenomena and good swimming spots as you walk along the coast towards the west. Turning inland at a wrecked ship lying just offshore, you pass through white sand dunes and enjoy breathtaking views of the tufa stone formations of the bay of Sarakiniko, which you can then explore at leisure, before heading to Adamas.
    The coastal walk from Phylakopi to Adamas
    Walk to Plaka: 11km
    Phylakopi to Adamas: 12km


We have found stylish, charming accommodation on each island. Since eating out is part of the experience of any Greek holiday, we do not include dinner.

In some places, we work with more than one hotel, as shown below. All are hand-picked by us and, unless there is a price implication (in which case we will contact you to discuss your options), we will tell you which one we have booked for you on your booking confirmation.

We particularly recommend adding extra nights in Athens and Milos, to give you more time to explore.
Prices & travel options
All prices are in £ sterling (GBP). If you'd like to see what they equate to in your currency, use the converter. For general information on pricing, see the 'your holiday price explained' page.
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  • 11 nights: 03 September 2023 - 12 October 2023, 06 May 2024 - 30 June 2024 & 01 September 2024 - 13 October 2024

    Start varies according to season* | End by latest date(s) shown above

    Starting Price Single room
    3 - 13 Sep 2023 £1550 £840
    14 Sep - 1 Oct 2023 £1475 £765
    6 - 29 May 2024 £1445 £730
    30 May - 19 Jun 2024 £1650 £855
    1 - 13 Sep 2024 £1705 £925
    14 Sep - 2 Oct 2024 £1625 £845
    3rd & 4th person discount £0
    Single traveller supplement £15 to £17

    Includes accommodation, meals and services integral to the holiday as described, plus walking notes and maps, but no travel from the UK, nor any connecting travel from the airport unless stated below.

    *Start days: any day in June & September. Otherwise any day except Sunday or Tuesday (to tie in with Athens-Serifos ferry, which does not run on Tuesdays and Thursdays outside the peak season)

    Included travel: outward transfer between port and hotel on Serifos and Sifnos; homeward transfer from last hotel to Milos airport and internal flight Milos to Athens.

    Pay locally for transfer from Athens airport to city hotel; transfer (by metro or taxi) from Athens hotel to Piraeus port; all ferry crossings; taxis/buses to walks (total approx €150pp).

    Book your flights through us and we'll find the best route and times to suit you. Please contact us to find out more about our flight booking service. We can also book connecting travel - see below.

  • Room upgrades (£ per person per night)

    Villa Notos, Adamas, Milos
    Deluxe studio: 01 Sep - 30 Sep 2023 £22
    Deluxe studio: 01 Oct - 12 Oct 2023 £9
    Deluxe studio: 06 May - 31 May 2024 £10
    Deluxe studio: 01 Jun - 30 Jun 2024 £24
    Deluxe studio: 01 Sep - 30 Sep 2024 £24
    Deluxe studio: 02 Oct - 13 Oct 2024 £10

    Extra nights (£ per person per night) in a double or single room

    If adding extra nights at the Herodion Hotel in Athens, the price is £163pp (£285pp in a single room)
    Philippos Hotel, Athens (B&B) Double room Single room
    03 Sep - 12 Oct 2023 £87 £150
    06 May - 30 Jun 2024 £96 £165
    01 Sep - 13 Oct 2024 £96 £165
    Hotel Delfini, Kamares, Sifnos (B&B) Double room Single room
    03 Sep - 12 Oct 2023 £60 £110
    06 May - 30 Jun 2024 £66 £121
    01 Sep - 13 Oct 2024 £66 £121
    Villa Notos, Adamas, Milos (B&B) Double room Single room
    03 Sep - 30 Sep 2023 £93 £131
    01 Oct - 12 Oct 2023 £77 £110
    06 May - 31 May 2024 £85 £121
    01 Jun - 30 Jun 2024 £102 £144
    01 Sep - 30 Sep 2024 £102 £144
    02 Oct - 13 Oct 2024 £85 £121
    As an alternative to flying, we can arrange rail travel from London

    Travelling from the UK

    Travelling from outside the UK

    If you are flying from outside Europe,  we recommend flying via Athens. To discuss onward connecting travel to the start of your holiday, please contact us.

    Outward route Airline
    Birmingham - Athens jet2 
    Birmingham - Athens (via Paris CDG) Air France 
    Outward route Airline
    Bristol - Athens Aegean Airlines,  easyJet 
    Outward route Airline
    Edinburgh - Athens Aegean Airlines,  easyJet 
    Outward route Airline
    Leeds Bradford - Athens (via Amsterdam Schiphol) KLM 
    Outward route Airline
    Gatwick - Athens Aegean Airlines,  easyJet,  Wizz Air 
    Outward route Airline
    Heathrow - Athens Aegean Airlines,  British Airways 
    Outward route Airline
    Luton - Athens Ryanair,  Wizz Air 
    Outward route Airline
    Stansted - Athens jet2,  Ryanair 
    Outward route Airline
    Manchester - Athens Aegean Airlines,  easyJet,  jet2 
    Manchester - Athens (via Brussels) Aegean Airlines 
    Travelling from outside the UK

    If you are flying from outside Europe,  we recommend flying via Athens. To discuss onward connecting travel to the start of your holiday, please contact us.

    This list of flight options should be used as a guide only, and you should check each airline’s website for current routes, frequency and schedules. Not all flights operate daily, and may not run for the entire season. You should also heed the latest flight arrival time and earliest flight departure time stated in the connecting travel section, as it may not be possible to arrange connecting travel outside these times. Please do not book your flights until we have confirmed your accommodation to you. Alternatively, our expert reservations team will be happy to offer advice and to make flight bookings for you for any of the options listed above. We charge £35 per person for our flight booking service. Your flights are then covered by our package-booking conditions, which give you greater protection in the event of delay or cancellation, as well as providing ATOL cover.

  • Prices below are based on 2 people travelling together. If you are travelling solo or as a party of 3 or more and our arrangements include a taxi, please contact us for prices; additional passengers often pay less.

    Where a price range is given, the price you pay depends on your date of travel.

    Connecting travel options - flying via Athens

    Outward route Price per person Latest flight
    arrival time
    own travel arrangements from airport to hotel pay locally flexible
    Homeward route Price per person Earliest flight
    departure time
    transfer hotel to Milos airport (0h30), domestic flight Milos to Athens (0h45) included 1400
What is included
  • 11 nights
  • 11 breakfasts
  • route notes and maps
  • GPS navigation
  • transfers from/to ports on Serifos and Sifnos
    transfer to Milos airport
  • domestic flight Milos to Athens

If you've experienced this holiday first hand, why not write a review?

We are keen for as many customers as possible to review their holiday. To make it easier to do so, we include a specific review section on our post-holiday questionnaire, and this is what we publish here, unedited. Read our full review policy >



If you have any questions relating to this or any other Inntravel holiday, our friendly travel experts will be happy to help. You might also find our General FAQs section helpful.
  • We’ll send you route notes and maps 2-3 weeks before your holiday. The route notes not only contain directions to get from A to B, but also include practical information about places of interest and eateries along each route, plus cultural information about the area. If/when you are moving between hotels, you leave your luggage in reception as you leave, and it will be transferred ahead to your next accommodation, meaning that all you need to take with you are a camera, sun cream, drinks, food and waterproofs.

    For more detailed information, see our walking holidays in Europe page.
  • Yes, prior to going on holiday you will be able to download GPX tracks so that you can follow your route on your smartphone or dedicated GPS device if you wish. It’s entirely up to you whether or not you use them – our detailed, step-by-step route notes remain the principal means of guiding you from A to B – but we provide them as a secondary means of navigation for additional reassurance when walking.
  • We can book a wide range of routes from the UK with a variety of airlines. As well as being more convenient for you to book all elements of your holiday together, it also means that we’ll accept liability for your travel arrangements, so if things go wrong, such as the airline going bust, we’ll make suitable alternative arrangements for you. The fee for this service is £35 per person (£15 for children aged 2-11). More information on flights >
  • We can’t book flights that originate outside the UK, but if you wanted to book your own flights to London (or elsewhere in the UK), we can make all onward travel arrangements (including flights) from there. Alternatively, if you are booking your own flights to an airport in continental Europe that’s appropriate for your holiday, we can book onward rail travel and/or taxis. More information about how we can tailor holidays for customers outside the UK >
  • Since our holidays are self-guided, we recommend calling us for a chat about your plans before making a booking, especially if it’s the first time you’ve booked with us.
    The price panel shows the supplement for a single room and also the single traveller charge (this covers (luggage) transfers and other costs which are usually shared between two people).
  • Once you’ve decided on your exact itinerary (our travel experts will be happy to offer advice), you need to provide us with your party’s details, either by phone or via our booking form. At this point we also ask you to pay a deposit so that we can secure a room for you immediately on confirming availability with the hotel(s). If it turns out that we can’t secure the accommodation for the holiday you’ve requested, or offer an acceptable alternative, we’ll refund your deposit promptly and in full. After booking your accommodation and other key elements, we'll then book your travel (or you can do so if you’re making your own arrangements) and send you a Booking Confirmation and Invoice.

    More information about the booking process >
    Information about accommodation, general practicalities and more >
    Booking conditions >
  • Yes, it’s something we insist on, even for holidays in the UK. The vast majority of holidays go smoothly, but when things go wrong, it can be expensive to put them right. Buying a new pair of walking boots after your suitcase is stolen mightn’t seem so bad, but the bill for being airlifted down from a mountain with a broken leg or flown home while still recovering from an illness or accident can incur a five or six-figure bill.

    Many insurers offer travel insurance (you can find details on our insurance page of a policy that you may like to consider if you are a UK resident), but you do need to make sure that you’re covered for medical emergencies – including falling ill with Covid-19 while on holiday – and repatriation. We also recommend that you are covered for other eventualities, such as cancellation and loss of luggage and passports.

    When you purchase a policy, be sure to check that it covers the activities you'll be doing on holiday and that it is adequate for your own individual needs.
  • It is your responsibility to ensure you are in possession of the correct travel documents, with the correct validity. If you’re a UK citizen, you need a full British passport to travel to Greece, but not a visa (please note, however, that a new travel authorisation system is being introduced). If you are a citizen of another country, you’ll need to check requirements with the national embassy or your own consulate.

    Current information regarding vaccinations and travel health advice for UK citizens can be found through the Travel Health Pro website. You must make sure you have adequate insurance cover for illness, accidents and repatriation (see the insurance question). You should also apply for a Global Health Insurance Card (GHIC) if your EHIC has expired (if you have a still-valid EHIC, you can use this until it expires).
  • The most commonly spoken language is Greek. The currency is the Euro. Greek time is GMT/UTC + 2. It uses Daylight Saving Time, so in summer is on BST + 2.
  • For information on the practicalities of travel now that the UK is no longer part of the European Union, visit
  • The UK Foreign, Commonwealth & Development Office (FCDO) provides up-to-date, country-by-country travel advice, as well as information on security, local laws, passports and visas for UK citizens.

    If you live outside the UK, see our essential travel information page for a list of relevant websites.
  • You are the best judge of your child’s/children’s capabilities. We are happy to take bookings for families of older children/teenagers if they walk regularly, love the outdoors and are comfortable with the distances and ascent/descent involved. Please note that the bedrooms at most of the accommodation we use will normally only sleep a maximum of 3 people, and sometimes only 2.
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