Hi All:
It's our first trip to Greece for us! We're booked on the 14 day Rick Steves' Greece tour in September, 2026. We would like to put together a bit of island touring following the conclusion of the Rick Steves tour. My guess is we have between 7-10 days available.
What itinerary would you recommend for first timers in the Greek Isles?
Many thanks in advance.
Excluding those in the Saronic Gulf, since I believe Hydra is part of the Rick Steves tour, the most easily accessible and best-known islands from Athens are the Cyclades. Those 22 islands are listed here:
https://www.visitgreece.gr/islands/cyclades/
9 or 10 days is a good amount of time to visit two islands, provided they are connected by ferry routes. So if you want to visit two islands in the same trip, first check how you can travel between them.
There are several ways to determine which island you want to visit.
If you're bothered by searching, just look at the most touristy and easy-to-combine islands, which will certainly be recommended here. These are Santorini and Naxos (which have airports). There's also Naxos and Paros, which is another easy pair to combine.
I don't recommend going to Mykonos unless you want to party, see celebrities, and spend a lot of money.
The other approach is to know why you're going to this island rather than another. I've visited many Greek islands, but I've never chosen an island without knowing why I chose it over another, and without considering what I could see/do there. So there are quite a few other possibilities if you do a little research.
Also consider transportation. If you really want to explore an island, a rental car is essential, and you'll need at least four or five full days. If you don't plan on renting a car, be aware that while some islands have a good bus network, others have almost none.
What are the dates for your tour? if it is in the second half of September you will end up with some of your extra days in October. The weather will be cooling down and the tourist season will be slowing down and the weather could be changing.
You may want to get to Greece before your tour and use that time to get over jet lag and do you island adventure. It will give you time to become familiar with the people of Greece and how their culture operates.
As already mentioned Naxos and Paros are two good destinations. There are daily excursion boats based in Naxos which go to Paros then go to Santorini, our the popular Delos ancient site plus a couple of hours on Mykonos. This will give you the opportunity to visit those very busy popular islands without having to pay for the expensive dining and hotels.
Here are some images of Naxos.
Naxos town 2024 https://www.flickr.com/photos/stanbr54/albums/72177720318203165/
Trip around Naxos https://www.flickr.com/photos/stanbr54/albums/72157634605629689
STanbr's "keyboard stutter" giving "Our" for "or" may give impression that a day-excursion covers both Mykonos & Santorini. Luckily, each is separate. Especially useful if cruise-happy friends insist you MUST see Santonini... this allows a few hours on the island for the Main Attraction... the Famous Caldera View ... a stroll along the rimside path will provide lovely photos ... then at 4:30 or so, you can hop back on the excursion vessel, and be back on Naxos for sunset in a relaxing environment.
To help sort through Stan's good suggestions, I'd add not to worry about the prices of dinners and hotels on Delos.
The island has been uninhabited for centuries, and the last temporary inhabitants were a few pirates. :)
OK, I was in a hurry which is the only excuse for the hiccups on my post.
Perhaps some images of Delos and Mykonos will make it all clear.
Day trip Delos and Mykonos https://www.flickr.com/photos/stanbr54/albums/72157637922138466/
Perhaps another option: ferry Athens to Sifnos, ferry to Milos, fly back to Athens. Worked well for us on our first trip to Greece. We loved beautiful, relaxing, unspoiled Sifnos. Milos is lovely but more touristy. Would happily return to Sifnos for an extended visit. But, then, we have not been to the more popular islands. Happy planning!
Which tour are you on (start date)? We are leaving on Sept 22 in Athens for 14 days. Then we are heading to Mykonos for a few days! It's our first visit to Greece as well so I will be following on this thread!
