Discover the Greek Cyclades: the best island hopping itineraries

Here you have some As far as you can-style ideas to spend your long-awaited summer holidays as best you can. Where? In Greece, in the beautiful sea of the Cyclades. Contrary to what we usually read in many travel blogs, only few of us can plan multi-week or monthly itineraries… We want to be more realistic! Therefore, I have suggestions and itineraries for you, which perfectly fit in with the two main characteristics that distinguish our trips: short and… during the high season!

When it comes to Greece, an island-hopping holiday is my favourite one. In one week or so you can visit several islands (also the tiniest ones), thanks to frequent and busy ferries that connect the island groups. Given the huge amount of possible itineraries, a neophyte could find it difficult to make a choice. For this reason, here you have some inspirational itineraries for your summer holidays.

Rule no.1: take your PCs and organise everything on your own.

Rule no.2: if you want to move between the islands during the high season, it’s better to book the ferries from your country. They are often late, so consider not to plan the ferry too close to the estimated time of landing.

Rule no.3: enjoy your trip, Greece is one of the most amazing countries in the world

Itinerary #1: Santorini and Ios

First time in Greece? This is probably the best itinerary for you. These two islands are close to each other, they are well connected and easy to reach.

Santorini (Thira) is easy to reach thanks to several direct flights, run by low-cost airlines. This island stands out for its breathtaking landscapes, for its postcard panoramas and, of course, for its glimpses dotted with small, white and blue houses, typical of the Cycladic architecture. Because of its volcanic nature the island cannot boast about its beaches as if they were the best of the whole country, but it’s still worth spending there 3-4 days. Once your stay in Santorini has come to an end, I highly recommend to go to Ios.

Within just 30 minutes by high-speed ferry you will continue your holiday on amazing beaches and in a more affordable accommodation. Ios is famous (especially among young people) not only for its fascinating Chora, the village centre, but also for its nightlife and parties, almost concentrated in Mylopotas beach. On the other hand, Manganari and Agia Theodoti are only two of the many oases in which you will find peace and quiet even in August.

MY ADVICE: don’t miss the Bilaeti tavern in Ios.



Traditional: in Thira, the capital city, in order to take advantage of the transport service which works around the whole island.
Romantic: choose Oia, more expensive and secluded, but unique for charm and panoramas.
Nice (and not expensive) hotel in Oia: Maria’s Place

Low cost: choose Kamari or Perissa, and both towns have the beach.

Nice hotels and studios in Kamari:

Nice hotels and studios in Perissa:

Ios Agia Theodoti Beach

Agia Theodoti Beach (Ios)

Ios Manganari Beach

Manganari Beach (Ios)

Santorini Sunset

Sunset in Oia (Santorini)

Itinerary #2: Naxos and Koufonissi (+ Mykonos)

This time you will land at Mykonos airport. In my opinion, during the high season, it’s impossible (and also too expensive) to stay on this island, therefore I suggest you to pay attention to the period in which you are going there. So let’s go to Naxos, which can be reached within one hour/one hour and a half by high-speed ferry. The whole West coast of Naxos is a series of long and beautiful beaches. Their crystal clear sea won’t disappoint you; Aliko beach (not equipped) and Mikri Vigla beach (fully equipped but with few umbrellas) are simply amazing. It’s true that with a car you could also visit the East coast, however, since it’s rather big an island and you are an island hopper, moving along the coast on a scooter for a stay of 5-7 days is perfect: the best beaches are here.

Now, you only need to move from one of the largest islands of the Cyclades to one of the smallest, Koufonissi (or Koufonissia), which belongs to the Micro Cyclades. Forget to use any motor vehicle: you will move across the island only on foot, by boat or by bike. The wonderful Pori beach is the absolute island’s queen, that you can reach by a (long) walk or by a boat, which leaves the port pretty often. After having been here you will forget all the other beautiful beaches that you saw on the way to Pori and you won’t be able to choose any other beach but this one for the following 3-4 days you will be staying in Koufonissi. Good choice, it is one of the most astonishing islands of the Aegean! Koufonissi’s Chora, although tiny, is really cute and it will be the destination of your nights.

MY ADVICE: in Koufonissi reach as far as the mill to enjoy an amazing sunset while sipping a cocktail.

SUGGESTED LENGTH: 12-14 days (depending on whether you want to spend a couple of days in Mykonos or not).


Mikri Vigla Beach (Naxos)


Chora in Koufonissi

Itinerary #3: Milos and Folegandros (+ Santorini)

This itinerary is a bit more demanding in terms of distance and connections, but it will give you a great satisfaction. Also this time, your airport will be in Santorini. You will decide whether or not to visit it. Anyway, you will then reach Milos within two hours and a half by high-speed ferry. Adamas is the village where you will dock and where most of the accommodations are. Milos is quite big an island, however in its West side streets are almost absent. No worries: promptly book one of the day-trips, which will make you discover the most wild side of the island by boat. In particular, the boat will bring you to Kleftiko bay, an ancient base for pirates which can be reached only by sea. In the other days you can visit some of the many beaches of Milos, such as Sarakiniko and Agia Kyriaki, to name but a few.

Once your visit to Milos has ended, go on with your tour moving to Folegandros. It takes one hour by high-speed ferry. This island, whose Chora is probably the most beautiful of all the Cyclades, will appear to your eyes like a rock emerging from the sea. I suggest you to spend on this island 3 or 4 days to enjoy its beaches (not always easy to reach) and having dinner in the small squares of the Chora.

MY ADVICE: in Folegandros, at least until a couple of years ago, there were only two scooter-rental firms. One of them doesn’t trust the Italian driving licence. Go to the other one!

SUGGESTED LENGTH: 12-14 days (depending on whether you want to spend a couple of days in Santorini or not).

Milos Beach

Milos Beach

Folegandros bay

Folegandros Beach

Itinerary #4: Paros (+ Mykonos)

Not enough time? There’s an itinerary for you too! Book your flight to Mykonos and, once you have landed, take an high-speed ferry to Paros. It takes one hour. Then choose where to stay, whether in Parikia (where the port is located) or in Naoussa (a bit more secluded, but characteristic). Paros boasts about really beautiful and easy-to-reach beaches, which will meet your expectations. Just another tip: don’t miss a day-trip to Antiparos, a tiny and almost uninhabited island, that you can reach in a few minutes by boat from Pounta.

MY ADVICE: discover the not so famous Agia Irini beach, one of the most amazing beaches I’ve ever visited in Greece!

SUGGESTED LENGTH: 7-8 days or more if you want to visit Mykonos.

Paros Agia Irini Beach

Agia Irini (Paros)

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Sono Martina, abito a Padova e nella vita, oltre ad essere un’instancabile viaggiatrice, sono una Web Developer a tempo pieno. Amo la fotografia. Spero di riuscire ad ispirare chi, come me, è animato da una grande passione per la scoperta di posti nuovi.


  1. ciao,
    interessantissimi tutti gli itenerari! 🙂
    sto valutando seriamente il numero 2 (sarà anche la mia prima volta in Grecia).
    due settimane di tempo bastano dunque?
    sarebbe x giugno o luglio.
    con tutti gli spostamenti c’è tempo x vedere abbastanza bene tutte e tre le isole? o sarebbe meglio lasciare Mykonos solo come base aeroportuale x andare e tornare?
    saluti 🙂

    • Ciao Lisa!

      Grazie, sono felice di sapere che i miei suggerimenti ti siano d’aiuto per la tua prima vacanza in Grecia 🙂
      Con settimane piene potresti fare qualche giorno anche a Mykonos. Non riuscirai a vedere tutto, ma ne avrai un assaggio!
      Gli spostamenti sono da incastrare, ma abbastanza frequenti tra queste isole, non avrai grandi difficoltà.

      Sarà un bel giro, vedrai!


  2. Hi!
    This is really useful., thanks a lot! We plan to spend two weeks as island hopping with start point in Andros (Airport Athens). I´m just wondering if necessary to book accommodation in advance when travelling in end of June/ beg. of July. We want to visit the “non touristic” islands, like Syros, Sifnos, Amorgos, Nachos and Folegandros.
    Any recommendations here?

    Thank you!
    Ciao, Lada

    • Ciao Lada!
      Thank you for your message, I’m glad to learn my article is helping you.
      You’re planning an amazing itinerary! You will enjoy it a lot.
      Talking about the reservations, I think it would be easy for you to find an accommodation.
      If I were you, I would check with more attention the ones in Folegandros, since in the last years the island has became quite popular and “cool”. But it is very small.
      I stayed at Solaris Hotel, not the cheapest, but very very nice.
      Let me give you one single suggestion about your route. I haven’t visited Syros, Sifnos and Serifos yet, but I’m quite sure that Serifos would be a better choice than Syros.
      Go for Sifnos + Serifos in my opinion.

      Hope it helps 🙂


  3. Ciao, bellissimo post ! Io e la mia famiglia amiamo la Grecia e questa è la terza volta che decidiamo di esplorare una delle isolette delle Cicladi . Quest anno abbiamo deciso di visitare Koufonissia e soggiornare una settimana intera nella piccola isola. Considerato che ho una bambina di 6 anni e solo una settimana da trascorre in Grecia, credi che il soggiorno di 6 giorni a Koufonissia sia troppo lungo? Meglio fermarsi 2 notti a Naxos e 4 notti a Koufonissia ? Sono alla ricerca di consigli! Grazie mille Sonia

    • Ciao Sonia,

      sono felice il post ti sia stato d’aiuto 🙂
      Koufonissia è davvero splendida, il mare è favoloso e perfetto per i bambini. E’ molto piccola e 3-4 giorni sarebbero sufficienti.
      Al contrario Naxos è grande, quindi in 2 giorni rischieresti di vedere poco.
      Considerato il tempo a disposizione e la bimba, 6 giorni a Koufonissi mi sembrano una buona idea. Sicuramente una vacanza tranquilla all’insegna del relax.


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