Two weeks in the Cyclades

The Cyclades attract a lot (a LOT) of people in the summer, and it's not always clear how to visit them.

For our first family trip to the Cyclades (in 2016), we took a route that seems great for discovering the islands: - Flight Paris / Santorini (Transavia) - 3 nights in Santorini - Ferry Santorini / Milos - 4 nights in Milos - Ferry Milos / Sifnos - 4 nights in Sifnos - Ferry Sifnos / Athens - 3 nights in Athens - Flight Athens / Paris

Santorini is the postcard image of the Cyclades... but not really any beaches for kids. My tip: you should stay in Oia because it's really "the spot" on the island. We chose the Pension "The Flower": simple but very well located and with a pool for the kids. Another tip: rent a car as soon as you arrive at the airport because the island is vast.

Our favorite moment: Oia around 6:00 AM, a paradise for photographers. It’s nothing like the daytime, or especially the evening when all the crowds rush in for the famous "sunset." Another favorite, the hike between Fira and Oia, 10 km, 4 hours of walking with extraordinary views (especially around Imerovigli). For the rest, we toured the island—it’s nice but nothing to marvel at.

After a 2.5-hour ferry ride, we arrived in Milos, home of the famous Venus de Milo. This is our favorite island in the Cyclades (though we haven’t seen them all!). In the port of Adamantas, we stayed at the Liogerma Hotel (very well located near the port).

Our favorite experience: the boat tour around the island (and swimming at Kleftiko). Absolutely a must-do, but book it as soon as you arrive because it’s often fully booked for the next two days.

I also recommend renting a car to explore this island. Other favorites: the incredible fishing village of Klima with its colorful boat houses, the rocks of Sarakiniko (best in the morning sun), the beach at Tsigrado (with its ladder access through the rocks), Plaka, the caves of Papafragas, the waters of Firopotamos, and Fyriplaka...

Just a 1-hour ferry ride, and you’re already in Sifnos. A small island with a bus network that means you don’t need to rent a vehicle. We stayed in Kamares (Hotel Afroditi).

Sifnos has charming villages typical of the Cyclades (Kastro, Apollonia), beautiful chapels (Chrisopigi, the Church of the Seven Martyrs...), and lovely beaches (Cherronissos, Platis Galios...). Our favorite: hiking around Faros and the Chrisopigi Monastery.

A 3-hour ferry ride takes you back to the port of Piraeus to visit Athens: the Acropolis, its museums, and the Plaka district. A little favorite of ours: the Archaeological Museum, slightly off the tourist trail... With this route, you’ll see the diversity of the Cyclades and Athens without wasting too much time on ferries.

PS: We also did the loop Mykonos / Paros / Amorgos / Mykonos, but that’s a good idea... for a second trip ;)

Santorini - Oia:

Santorini:

Milos: Our absolute favorite!

Milos, always Milos...

Milos then Sifnos (also very beautiful).

Sifnos:

And Athens to wrap up this wonderful family trip...

Thanks so much for this new update, Manu—it’s giving me even more ideas! 😎 Have a great day, Christelle

Thanks Christelle,

We recommend this itinerary for your first trip to the Cyclades. Santorini is really different from the other islands (even though Oia plays a big part in the charm of this island, which doesn’t have many beautiful beaches).

Milos and Sifnos are typically "Cycladic" islands, and as you’ve gathered, we fell HARD for Milos—it’s the most beautiful island from our two trips to the Greek islands.

Ending with Athens adds a "cultural" touch, even though we mostly just did the Acropolis and its surroundings (the summer heat didn’t allow for much more, whereas on the islands, we never suffered from the heat... there was always a little breeze to "cool us down").

Hi Manu

Thanks for the lovely photos 🙂

I’m thinking about a (first) trip to the Cyclades in spring or autumn, and I’m a bit lost when it comes to choosing which islands... they all look amazing (not to mention everyone’s different favorites 😎). Especially since I was also considering Mykonos (not for the bling-bling side but for the visit to Delos and the direct flight). Result: I change my mind every two days! Anyway, I’ll keep exploring....

We only passed through Mykonos. The airport is well connected, and we found a really nice little family-run hotel for the first and last nights of our stay: Galini Hotel - Laka Square Tel. 306944923960 galini-h@otenet.gr

As the lady put it, "it’s really more for 18-year-old girls with legs a meter long!"...

Hi Muriel,

A direct flight to Mykonos is definitely convenient, but watch out for accommodation prices on the island. You might find a cheap flight, but if you have to pay 300 € a night on Mykonos, it quickly becomes less appealing. Luckily, there are always ways to find budget-friendly rentals, but avoid spending too much time on this island if you're no longer 18 or don’t have 1.20 m legs 😉 You’ll also find several huge cruise ships full of Americans there—not exactly a change of scenery That said, Delos is a must-see, and unfortunately, the easiest way to get there is through Mykonos.

Sifnos and Milos are really nice, as you can see from Manu’s photos! But since their trip in 2016, prices have gone up quite a bit.

Elenitsa

Just so you know, the Galini was 122 € per night (back in 2020). Expensive, but it’s in Mykonos and super well-located (5 mins from buses and taxis)

Hi everyone,

I’m way past 18, and anyway, I never had legs that were 1.2 meters long

Otherwise, I’ve spotted a few places to stay for under 100 € a night (in May), but I haven’t looked into the details yet—like how easy it is to get around—until I’ve settled on my route.

These photos are gorgeous! We’re heading to Greece from May 1st to May 18th, 2026. We land in Athens and plan to stay there for 3 nights. For now, the island I *really* want to visit is Amorgos, so that leaves 2 more to choose... not easy to decide 🙂 ... especially considering the boat trips... Also, do you think it’s important to book accommodations well in advance? We won’t be traveling *right* in peak tourist season...

Thanks! Christine

Hi Christine,

No, there’s no need to book accommodations too far in advance. A month before is plenty. Just make sure to return to Athens a day or two before your return flight. There can be boat delays or other issues, and you wouldn’t want to miss your plane.

Happy planning! Elenitsa

Thanks! I’ll definitely keep that in mind!!!

🙂 Christine

Hi Christine,

In May, there will indeed be fewer people than in August. But why wait until the last month? Personally, I'm an "early bird" and I book way in advance with a "cancelable" option.

For your choice of the 3 islands, you already have Amorgos as #1. You also need a second island with a return airport (to avoid going back through Athens (?)), so I recommend Santorini as #2 (and especially I recommend staying in Oia).

That leaves the 3rd island... we've done Paros and Mykonos, but they're further north. We also loved Sifnos and Milos... and I suggest Milos as #3 (even though one is full west and the other full east of Santorini). The real issue is that Amorgos is very far from Athens...

You'll have the white villages and the crater of Santorini, the wilder side of Amorgos, and the charm of the beaches and the blue sea at Milos...



A few photos of Amorgos to tide you over until spring...

It's a good idea to book in advance too, but sometimes not all accommodations are listed online. That said, even a month before, you can always find something. Just keep in mind that this works when traveling in May, but definitely not during peak season!

Personally, I can't stand Santorini and Mykonos—they're way too touristy even off-season, too expensive, and no longer authentic. Amorgos is indeed far from Athens, but that’s why it’s stayed quieter and more authentic since it’s less accessible than islands with an international airport. From Amorgos, you can also head to Koufonissi and Donoussa, which are the "Little Cyclades." They’re very peaceful. I also really like Sifnos and Milos. From Milos, you can spend a day on Kimolos, just 30 minutes away by boat. This tiny island is a haven of peace—you’ll feel like you have the whole place to yourself. It’s really lovely.

Note that you can also fly back to Athens from Milos. Some ferry schedules for May are already online. Check out www.ferryhopper.com. Have a great trip!

Thanks for this travel journal and the really lovely photos.

It's good to book in advance too, but sometimes not all accommodations are listed online. That said, even a month before, you can always find a place. Just keep in mind that this works when traveling in May, but definitely not during peak season!

Personally, I can't stand Santorini and Mykonos—they're way too touristy, even off-season, too expensive, and no longer authentic at all. Amorgos is indeed far from Athens, but that’s why it’s stayed quieter and more authentic since it’s less accessible than islands with international airports. From Amorgos, you can also visit Koufonissi and Donoussa, which are the "Little Cyclades." They’re very peaceful. I also really like Sifnos and Milos. From Milos, you can spend the day on Kimolos, just 30 minutes away by boat. This tiny island is a haven of peace—you’ll feel like you have the whole place to yourselves. It’s really lovely.

Note that you can also fly back to Athens from Milos. Some ferry schedules for May are already online. Check out www.ferryhopper.com. Have a great trip!

Hello! We actually didn’t plan to visit Santorini (it’s probably very pretty, but too touristy for our tastes). For now, here’s what we’ve decided: from the 2nd to the 5th, we’ll visit Athens, then head to the Cyclades, where we’ll spend 3-4 days on each island: Amorgos, the Little Cyclades, and Paros. Or Amorgos, Paros, and Serifos or Sifnos—but I’m worried that flights back to Athens might be less frequent from those islands (Serifos or Sifnos) since we’re traveling in May. Our flight to Montreal is on May 18th. You mentioned a flight from Milos to Athens—is it expensive? Since you live in Greece, I think your advice is really valuable. I’ll also check ferryhopper.com.

Thanks in advance for your suggestions.

Christine

Hi there,

For the price of the Milos-Athens flight, it’s like any flight ticket: it depends on the period, the days, etc. Two airlines serve Milos: Sky Express https://www.skyexpress.gr/fr and Aegean https://fr.aegeanair.com/. Check these sites for the price on your desired date.

From Sifnos and Serifos, there are 2 or 3 departures per day in May. Some days, there are even 4 departures to Athens.

ELenitsa

Hi there!

Thanks for the info... it’ll be really helpful. Stay warm in Quebec tonight—snowstorm and all! ;-) Christine

Thanks for your reply and the lovely photos!!

We haven’t quite decided on the islands yet... aside from Amorgos. We’re considering either Amorgos, the Small Cyclades, and Paros, or Milos, Amorgos, and Paros with a return flight from Athens. The idea is also to not waste too much time on boats and to visit islands that each have their own unique charm... To be continued... 🙂 Christine

So Amorgos and Paros are confirmed. The only question is whether to choose Milos or the Small Cyclades.

I don’t know the Small Cyclades, but Milos remains our favorite island in the Cyclades...