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Island Hopping in the Greek Cyclades

Brilliant sunlight, Aphrodite, and the Aegean Sea
Incredible views | Above the small village of Kallitsos on Serifos are some of the island’s finest vistas.
Insights into the past | And traditional ways of life on Sifnos’ many excellent walking routes.
Volcanic terrain | The dramatic white formations on Milos sculpt a lunar-like landscape.
Island-hopping experience | A sense of freedom and adventure, as well as time to relax.
What is included
  • 10 nights
  • 10 breakfasts
  • route notes and maps
  • GPS navigation
  • transfers between ports & hotels on all islands
  • domestic flight Milos to Athens
  • all ferry journeys
  • Island Hopping in the Greek Cyclades
    Brilliant sunlight, Aphrodite, and the Aegean Sea
  • Follow signed walking routes
  • The bay of Livadakia on Serifos
  • Locals still use mules to get around
  • Well-maintained routes on Sifnos
  • Stop for lunch or a drink in an inviting village square
  • Walk to a remote monastery on Sifnos
  • Enjoy far-reaching views to neighbouring islands
  • Delicious, fresh Greek salads
  • Apollonia, the capital of Sifnos
  • The colourful fisherman's cottages at Klima on Milos
  • Explore the lunar-like landscapes of Sarakiniko beach on Milos
What is included
  • 10 nights
  • 10 breakfasts
  • route notes and maps
  • GPS navigation
  • transfers between ports & hotels on all islands
  • domestic flight Milos to Athens
  • all ferry journeys

Holiday information

​A walking holiday in the Cyclades

One of the most popular and fascinating island groups in the Aegean, the Cyclades are 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. A quiet, traditional way of life has been preserved on many of the islands, and the warmest of welcomes awaits the traveller.
After spending your first night in the port city of Piraeus, near Athens, your island-hopping travels begin, during which you discover three of the lesser-known islands of the Cyclades archipelago – Serifos, Sifnos, and Milos.

Sailing across the cobalt-blue waters of the Aegean by ferry (fares included) and with plenty of time on each island for leisurely exploration, you can take in the picturesque white villages, undulating hills, and castle of Serifos, the terraced hillsides, cobbled lanes, and wide bays of Sifnos, and the surreal, white pumice cliffs on Milos – the very island where the Venus (or Aphrodite) de Milo statue was discovered.


Itinerary

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 Piraeus
    Night 1: at Port Square Hotel (where you spend one night).
    As your first night’s accommodation is on the day of travel, Day 1 is your first day of exploration.
  • Travel to Serifos
    At the port just a 10-minute walk from your hotel, catch the ferry (2h30) for the island of Serifos. The arrival by boat is considered to be the most beautiful approach to an island capital anywhere. Your two nights on the island are spent at the Aigaion Apartments or Galazio Suites.

    Since the ferry from Piraeus arrives on Serifos around lunchtime, you’ll have the afternoon to explore. We suggest the following walk.

    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 this medieval castle remains, but the views are superb, stretching over the bay of Livadi, the treeless landscape of Serifos, and towards the island of Sifnos.
    Arriving on Serifos
    Chora's Castle walk: 3km each way
  • Day on Serifos
    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 recommend the route below for today (or you can choose to do the walk to Chora’s castle if you didn’t do it yesterday).

    The Hills of Kallitsos: 6km, 2.5hrs; ascent 310m/descent 330m; longer version 11km, 3hrs
    Take a bus or taxi to Taxiarchon monastery (pay locally). From here you follow an enchanting old kalderimi (traditional, paved footpath) in the hills above the small village of Kallitsos on the island’s north-eastern coast, enjoying some of the island's finest views as you continue to Chora. From here, you can return to your hotel by bus, taxi, or on foot.
    Walking back towards Chora
    The Hills of Kallitsos: 6km
  • Travel to Sifnos
    You take the boat 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 four nights on Sifnos are spent at the Petali Village Hotel in the centre of the island. If you have time on arrival, you could head out on a walk (see Days 4-6).
    Port of Kamares on Sifnos
  • Choice of routes on Sifnos: 5.5km to 9km
    We provide notes for a choice of walks here (accessed by bus or taxi; pay locally) which we’ve listed below. If you’re looking for a more relaxed activity, however, why not make the short walk from your hotel to potter in the nearby historic village of Artemonas, overlooked by its two traditional windmills?

    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 route takes in 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 form a friendly welcome after quite a steep descent. Wander out onto the promontory by the first bay to admire the Chrisopigi monastery on its rocky platform, before continuing round the coast to Faros Bay where you can enjoy some time on the beach. When you’re ready, you can take a bus back to Apollonia (pay locally).

    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 into 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. Return by bus to your hotel (pay locally).

    From Apollonia to Kamares: 5.5km, 2hrs; ascent 133m/descent 307m
    Following an old mule trail to the small harbour village of Kamares (you’ll remember arriving here by ferry from Serifos), your walk winds down the hillsides from Apollonia, descending into a rugged, yet peaceful, pastoral world. Along the way, you pass the quiet chapel of Panagia Platanissa (or Platanou) – its whitewashed walls gleaming against the earthy colours of the surrounding terrain. From Kamares, you return by bus to Apollonia (pay locally).
    Traditional footpath through terraces
    From Apollonia to Faros Bay: 8km
    From Apollonia to Kamares: 5.5km
    Circular walk from Apollonia to Kastro: 9km
    From 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 will be at either the Thalassitra Village Hotel or at Villa Notos.
    Bay of Adamantas
  • Choice of routes on Milos: 7km or 8km
    On Milos, inviting paths lead along sandy beaches to secluded bays with panoramic views over the glittering sea. We provide notes for two walks.

    From Plaka to Adamas: 7km, 2.5hrs; ascent 220m/descent 372m
    After travelling by bus or taxi (pay locally) to Plaka, the traditional capital of Milos, you’re free to explore its medieval alleys and marvel at its glorious views over the bay before starting your walk. Setting off, you pass the ancient theatre, the early Christian catacombs, and a replica of the Venus de Milo statue that was found nearby. From the tiny harbour of Klima, bright and cheerful with its multi-coloured doors and balconies, you descend back to your hotel.

    From Phylakopi to Sarakiniko: 8km, 3hrs; ascent 202m/descent 187m
    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 back to Adamas by bus or taxi (pay locally).
    Walking above Plaka
    From Plaka to Adamas: 7km
    From Phylakopi to Sarakiniko: 8km

Accommodation

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.

For room upgrades, please ask at the point of booking about any available, such as a room with a private pool at the Thalassitra Village Hotel for a special end to your holiday.
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: 13 April 2026 - 11 June 2026 & 01 September 2026 - 21 October 2026

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

    Starting Price *
    13 - 30 Apr 2026 from £1293
    1 May - 1 Jun 2026 from £1393
    1 - 30 Sep 2026 from £1473
    1 - 11 Oct 2026 from £1293

    * Final price is subject to change due to the customisable nature of our holidays and is dependent on accommodation availability for the dates selected. We will contact you to confirm the final price. Single supplements are applicable on many of our holidays. Please contact us for full details.

    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.

  • RECOMMENDED AIRPORT(S):
    Athens
    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.

    Travelling from outside the UK
    We have many years' experience catering for customers who live outside the UK, and will be happy to make tailored arrangements to fit with your plans.

    You have two options:

    1) Book your own flights to London, from where we can book flights and onward connecting travel to your hotel.

    2) Book your own flights direct to an airport appropriate to your chosen holiday. You can either make your own way from the airport to the hotel, or we'll be happy to book onward connecting travel for you. Please consult with us before booking your flights, so that we can advise you on the suitability of your proposed route and timings.
    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
Reviews

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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 >

FAQs

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.
  • 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 www.gov.uk/visit-eu-switzerland-norway-iceland-liechtenstein.
  • 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.
Island Hopping in the Greek Cyclades
10 nights
Price from £1,293pp
Island Hopping in the Greek Cyclades
10 nights
Single-centre walking, no car
Grade: Easy-to-moderate
Price from £1,293pp
Last fetch time is : 2/7/2026 7:27:03 AM

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