Ferries between Naxos and Milos don’t start until June 7th (one each way, every day after that). Ferries between Santorini and Milos start April 28th and there is one every day in each direction. And there are always ferries between Naxos and Santorini. So if the dates work I would fly to Santorini (the longest leg) then ferry to Milos then Naxos and back to Athens. But if you need to travel between Naxos and Milos before the 7th then ferry Athens to Milos to Santorini to Naxos and back to Athens.
I’m traveling to Greece for the first time, and I’m so fortunate to be staying for about 9 weeks (peak season, unfortunately, I’m an educator and it’s summer!). I have ample time planned in Athens, and the Peloponnese (with rental car). Here’s where I need some help and suggestions. I have 5 weeks saved for the islands and I’m still trying to figure out how to spend them. I’m not sure if I’d like to cover just a few islands and soak them in a bit deeper with longer stays…or to travel at a quicker pace covering several islands in each main area (the Cyclades, Ionians, Crete-Rhodes Dodecanese, Eastern Islands) I’m an easy traveler and enjoy diversity. I crave spending time with locals and interacting with families – home stays at times, I enjoy the water and I’m an avid diver, I like hiking and exploring. Also, want to perhaps relax a bit – food/wine tasting welcomed). I’m excited about the trip and my ideas are racing all over. Do you have some ideas and suggestions to share? A rough sketch itinerary for Greece? Thanks so much!
Nine weeks in Greece is a dream itinerary it certainly gives you lots of flexibility. As you seem to have Athens and the Peloponnese sorted, you just need to sort out your five weeks on the islands. What you need to realize, however, is that the islands are not all mutually interconnected, but rather they are ‘grouped’ – both administratively and from the point of view of transport routes. Here are the main groups.
I’m hoping you can help myself and a friend decide where to go. We are hoping to go away around mid August for 10 days-2 weeks. We’re looking for a sunny place and beaches to tan and relax during the day, with some big nightlife and a good strip (the odd daytime activity maybe too). However we are in mid 20s so want to go somewhere with the same age group or older. I’ve been to Zante and although it was super fun at the time (I was about 18) and loved having the strip etc, just don’t want to be the older people there anymore! Money is also fairly tight, so nothing too expensive (was thinking santorini maybe before hearing the price along with it).
The Greek islands have beautiful weather in the months just before and after peak season. It’s a great time to see the islands, save money, avoid the crowds, and still have great weather (though not as hot as July and August). If you want to see the super-popular islands of Santorini, Rhodes, Corfu, and Crete without the tourists then this is a great time to visit.

Hi! I have fallen in love with the cyklades and have visited Santorini, Ios, Naxos and Folegandros in late june. Folegandros was the best, a fantastic island. We are now thinking about going to Paros the last week in September. Naoussa seem to be a great place. What’s the weather like in late September? Is it still quite warm? I also wonder about the sea conditions. May the sea be rough at that time of the year? I don’t like wavy ferry rides 😨 Thank you for a good sight!
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