Last July, we went to the Cyclades for the first time. We’d been tempted by these Greek islands for so long! We had already visited several islands in Greece: Corfu, Kefalonia and Ithaca on the Ionian Sea, and also Crete, but we didn’t know the Cyclades yet. We first considered renting a sailboat, but I was wary of the infamous meltem, the strong wind that can be fierce in summer… If I’m not mistaken, Ulysses had some trouble with it… I didn’t want to deal with it: Papa Voyage is a good skipper; I’m not quite a top crew member yet! So, we opted to travel between the islands by ferry. And on each island, we chose to get around on foot and by bus! Which Cyclades islands to choose? We chose Santorini, Milos and Sifnos. Three islands, three vibes. We loved all three for different reasons. Here’s our take on each and the details of our itinerary…

Santorini with kids: 3 nights

We started with Santorini, the most touristy, because we thought it best to visit as early in the season as possible. I was expecting such huge crowds that we were pleasantly surprised. It was not crowded at all! The island was very calm and most tourists gathered only in Oia at sunset – yet there are so many other spots to admire the setting sun!

Santorini, the “pros”:

• The caldera, the caldera, and the caldera! You can’t get enough of those views from the edge of the ancient crater! Hiking the trail between Fira and Oia is a must!
• The typical Cycladic architecture: little white houses, blue domes, windmills…
• Oia in the morning with no one around for a refreshing dip at the bottom of the steps.
• Plenty of villages to explore: Megalochori, Pyrgos, Emporio…
• Frequent buses to get around the island.

All the details of our walks and visits in Santorini are in my article Santorini, with kids, on foot and by bus.   Santorini, the “cons”:

• Santorini isn’t the island to choose if you’re mainly after swimming spots, so I don’t think it’s ideal for a holiday with young children. Ticoeur and Titpuce enjoy hiking, so it was perfect for us, but for little ones, there are more child-friendly islands! That said, every morning Ticoeur and I enjoyed a swim at Amoudi Bay, a little cove at the foot of Oia (the sea temperature was around 20 degrees).
• Oia from 5pm onwards is chaotic: people queueing to take photos at specific spots… If you’re like us and not a fan of crowds, don’t go to Oia in the early evening.

Good addresses in Santorini:

We loved our accommodation in Finikia, 20 minutes on foot from Oia. Those 20 minutes made all the difference! Our village was very peaceful and really pretty, with very narrow alleys. Our Cycladic home was called: The House of the Seven Ships.

In the peaceful alleys of Finikia

As for restaurants, we tried to avoid trendy places. At Taverna Mou (in Finikia), we felt like we were back in our previous trips to Greece. Live traditional music in the evening, small tables, and homemade food. For good ice cream, stop at the The Family bakery in Megalochori.

Milos with the family: 4 nights

Milos mainly tempted me because of the beauty of its coves – and indeed, when it comes to swimming, we absolutely loved it! It’s an island with a history marked by mining. The population was very poor and worked extracting sulphur and minerals. Many remnants of that time still remain. Milos is also the island of the famous Venus! And sorry, we didn’t manage to find her arms!

Milos, the “highlights”:

• Swimming in dream locations! Firopotamos, Sarakiniko, Firiplaka, Kleftiko…
• The colourful village of Klima!

Milos, the “downsides”:

• As on other islands, we got around by bus and on foot, but we ended up walking quite a bit along roads (granted, they were quiet) because there were no pedestrian paths.
• Boat excursions were a bit of a headache! It’s a big business on the island and prices vary widely! I didn’t always feel the price matched the service… I’ll tell you more about our experience in my Milos blog post.

Good spots in Milos:

We liked our accommodation in Triovasalos (called “Milos Cottage“, found on Airbnb): a former little shepherd’s house, very simple (warning: it’s really tiny! If you need space, skip it…). Our host Elena was lovely. We did have quite a few mosquitoes… but that might have just been bad luck… Also in Triovasalos, there’s “this flat with a terrace“. In terms of buses, staying in Triovasalos means changing at Adamas; however, it’s convenient for walking to several places. In Adamas, I didn’t find any accommodation that suited us, but have a look anyway. As for restaurants, our top favourite was Ergina in Tripiti (we ate there twice!). Medusa in Mandrakia was also nice, though more touristy.

Sifnos with the family: 4 nights

Sifnos was the obvious stop between Milos and the Athens port. I’d read it was a favourite island among Athenians, so I was surprised to see that 100% of the tourists were… French!! The island was peaceful, quiet, not too busy so there was no issue with crowds, but it did feel a bit strange – like being in France. I didn’t know the island was so popular among French families. Some even seem to have second homes there.

Sifnos, the “highlights”:

• The perfect island for hiking! There are marked trails all over! To enjoy it fully, go in spring or autumn. Still, we explored a fair number of trails and it was really pleasant to walk along such well-maintained paths.
• The village of Kastro where we stayed! Note: it’s very small so best to avoid during high season. In July, it wasn’t too crowded.

In the alleys of Kastro

• An island mainly visited by families because, although it’s great for hiking, there are plenty of child-friendly beaches: clear, shallow water.

Sifnos, the “downsides”:

• The bus connection timetables don’t seem to be well thought out. As we enjoy walking, it wasn’t a problem for us: instead of waiting for the next bus, we often continued on foot. But for families relying entirely on the bus, there can potentially be a long wait in Apollonia.

Recommended places in Sifnos: While we loved Kastro, I wouldn’t recommend our accommodation as it was really too small and had only a tiny outdoor space. I think it would have been fine for two people. But staying in Kastro is lovely, so take a look at what larger options you can find for a family: accommodation in Kastro. To optimise bus travel, you could also look for a place in Apollonia. It’s pretty and lively, even if I prefer Kastro. As for restaurants, we loved eating at Kaptain George, run by a family of fishermen located right at the bottom of Kastro, in the cove where Ticoeur is playing in the waves:

Before or after the Cyclades: a break in Athens.

Summer isn’t the best time to visit Athens, because unlike the Cyclades, it gets extremely hot! But as you’ll likely spend a day or two there before or after taking the ferry, feel free to reread the article I wrote during our previous trip to Athens in spring 2018. For accommodation, if it’s your first time in Athens, I recommend staying in the charming district of Plaka. As this time we were just passing through, I booked a more impersonal and out-of-the-way hotel, but it had a pool so the children could cool off. We could even see the Acropolis in the distance: Athens Panorama Projects. Not a charming hotel, but modern, practical, and good value for money.

Practical information for visiting the Cyclades:

Weather: in July, we had temperatures between 25 and 28 degrees Celsius. The seasonal averages for July-August are 27–28 degrees. Of course, the weather can always surprise you, but we chose the Cyclades because they’re known to be cooler than other southern European destinations, thanks to the local wind (the Meltemi). For me, as long as it’s under 30 degrees, it’s perfect! The sea was 22 degrees in Santorini and 25 in Sifnos and Milos. Tourism: we recommend going early in the season… even Santorini was pleasant! If you have no choice but to travel during peak season, you might skip Santorini and keep Sifnos and Milos on your itinerary, replacing Santorini with a less touristy island, such as Serifos, which lies on the ferry route between Sifnos and Athens, or Folegandros to the east of Milos. Budget: it was clearly more expensive than our other trips to Greece. The ferry prices in particular were very high — especially for a family of four. It’s definitely motivating me to sail next time! Prices vary greatly, especially depending on fuel costs, so I recommend checking fares for your planned routes before booking a trip to the Cyclades. For reference, I booked our ferries a month in advance, but had been monitoring them for three months and saw no change. Fortunately, we saved a lot by not renting a car at all on the islands: lots of walking and a few buses — it was perfect for us! Finally, I’ll soon be writing a detailed article about each of these three islands!

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Have you been to the Cyclades? Which islands would you recommend?