Which Cyclades islands should we choose?

Hello,

In the past, I’ve met travelers—twice, actually—who did things this way over a long period: they’d book accommodation on one island and then take short trips (3 or 4 nights) to other nearby islands. They were Americans and Australians.

I’m not sure if this is exactly what you’re considering, but it *can* work. That said, it means you’ll keep paying for nights on your base island even when you’re away, and you’ll also have to pay for round-trip ferries instead of just one-way hops between islands. On the plus side, it lets you leave some luggage behind and only take the essentials for 3 days.

If you go with this method, Paros and Naxos are both solid bases, each with its own advantages depending on ferry routes. But don’t expect to visit another island with just a day trip or even a single overnight—3 nights (2 full days) is the absolute minimum.

With the islands you’ve picked, here’s what I’d do instead:

Athens → ferry or flight → Paros → ferry → Naxos → ferry → Santorini → direct Aegean flight → Istanbul.

Another option is to take a connecting flight to Naxos, Paros, or Santorini the same day you arrive in Athens, and save Athens for the end of your Greece leg. From Athens, you’ll have daily flights to Istanbul, whereas Santorini only has 2 direct flights per week (at least in Sept/Oct 2026).

For the island portion, you could also do something like: Santorini → ferry → Naxos → ferry → Paros → ferry or flight → Athens.

You can easily cut Santorini down to 3 days instead of 4 (or even 2 days/3 nights). Up to you!

I can’t really comment on the Greek islands, except that I’d have planned one extra night in Athens to adjust to the time difference and enjoy the city (unless you’ve already visited it).

In Istanbul, there’s a lot to see in the area around Hagia Sophia: Topkapi Palace, the Blue Mosque, the Museum of Islamic Art, the Roman Mosaics Museum, and the Basilica Cistern. Not far away is the Süleymaniye Mosque.

The European district (Pera) is a big change of atmosphere. Around Istiklal Caddesi, there’s a huge number of restaurants and shops tucked away in small side passages—pick out some restaurants in advance. You can eat *really* well in Istanbul! Near Istiklal, there’s the Museum of Innocence if you’re familiar with the author Orhan Pamuk (if not, you’ve got time to read the book of the same name!).

At the end of the Golden Horn, there’s Miniaturk Park, which features replicas of all the important buildings from the former Ottoman Empire (like the Mostar Bridge, etc.). In the western part of the city, you’ll find the Byzantine church of Chora (Saint Savior in Chora) and a beautiful mosque nearby. Along the Bosphorus, several palaces and attractions are worth visiting (Dolmabahçe Palace, Ortaköy Mosque, Beylerbeyi Palace, etc.). Finally, if you’re a bit of a foodie, you can cross over to the Asian side—Kadiköy has several streets with fruit and vegetable markets and great restaurants.