Seeking help with my itinerary for a first time trip to Greece in May

We were in santorini in this past May and it was busy but according to people there, nothing like the peak tourist season.

I would skip Mykonos and go to either Naxos or Paros instead. Why go to the two most touristed islands? We picked Naxos and absolutely loved it. As my twenty something sons said “it is even better than santorini!” I close Naxos because had gorgeous beaches, history, charming towns, and mountains. We were there 4 nights and would have happily stayed another night or two.

Naxos has a tourist infrastructure but is cheaper and far less crowded than either santorini or Mykonos.

We stayed at Kymata in Naxos and would highly recommend it.

It will be plenty busy. Paros and Naxos are very similar in terms of things to see and do. I prefer Paros, and from there you can easily take a daytrip to Antiparos. If you want to go to Delos the boat trip in the open sea from Paros is shorter than if you begin on Naxos.

I too would skip Mykonos and replace it with either Paros or Naxos. I preferred Naxos ... St George Beach .. Hotel Kalergis, right on the sand, perfect for long walks but yet close to town.

I’m not sure if the day trips to Mykonos will be running when you’re there in May, but if not there is plenty to do on Naxos (or Paros, if you choose that).

Is there anyway you cannot stay in Fira? Instead stay in Oia or in between Fira and Oia, like in Imerovigli on the caldera? Fira gets the crush from the cruis ship boats and is more tacky. Oia is classically beautiful. You will have it to yourself early in the morning and in the evening. You say you are fit, so you would adore the old donkey trail between Fira and Oia (takes about 3 hours, stunning landscape against the bluest of seas).

I went to Mykonos before Naxos in October when it was not party season and enjoyed it. But when I finally got to Naxos, I enjoyed it more. So yes, split your time. You are young and have energy. See both islands.

I visited Mykonos, Naxos and Paros in September. Mykonos was nice but Naxos and Paros (Naoussa) were outstanding. As a single woman I would pick Naxos as there is alot to explore in the old town including a few nice little museums, more dining options and a pleasant beach walk. Nice water to bob in and beach cafes lining it. We also stayed at St George Beach area.

On Santorini, my wife and I stayed in Imerovigli, and found it to be a great location!! For meals, Aktaion (in Firastephanie) was one of the best I have ever tasted: authentic, full of flavour, highly recommended by our Airbnb hosts. Galini Cafe served a delicious breakfast, and it gives a beautiful view of the Caldera.

On Naxos, you’ll find even more delicious, authentic Greek cuisine, for a fraction of what it costs in North America! Among our favourites: Doukato, and Apostolis Taverna were great for memorable suppers, and Boulamatsis was amazing for more casual lunch, with delectable comfort food. Flamingo offered a beautiful courtyard with music, and entertaining service, and the food was quite good, but just a notch below the others.

I see you are getting several suggestions that you skip Mykonos but not really why people are suggesting that. Mykonos town is lovely and is well worth a visit. However Mykonos has chosen to market itself as a high end jet setter party island. Its not really a party island in May thats more common in the high season. However while Santorini has that outstanding Caldera view Mykonos doesn't offer anything more than Paros and Naxos. They have the same white and blue buildings, as good or better beaches and at prices less than half of what you will pay on Mykonos. Mykonos is priced like Santorini and many of us are not willing to pay that kind of money when there are options that provide a more authentic Greek experience nearby.

If Delos is a must see for you it can be done twice a week by excursion boats from Naxos which stop in Paros on the way. The trip gives you about 3 hours on Delos and three in Mykonos.
Here is what that is like
Day trip Delos and Mykonos http://www.flickr.com/photos/stanbr54/sets/72157637922138466/

Our favourite island is Naxos. It will probably be more active than Paros in May. At that time of year you will want to stay at St George beach as it is part of Naxos town and the whole tourist infrastructure will be up and running. You get a beach vacation plus all the activities of town.
Here is what St George is like plus images of several hotels we have visited.
St George Beach Hotels Naxos http://www.flickr.com/photos/stanbr54/sets/72157632162394787/
St George Beach Naxos http://www.flickr.com/photos/stanbr54/sets/72157632113170279/

And here is why we love Naxos.
Naxos Town http://www.flickr.com/photos/stanbr54/sets/72157632094558042/
Trip around Naxos http://www.flickr.com/photos/stanbr54/sets/72157634605629689/
Naxos sunsets https://www.flickr.com/photos/stanbr54/albums/72157700728046481

Hi everybody,
Thank you for all of your suggestions. I really appreciate it.
I decided to split up my time and visit Naxos and Mykonos with 2 nights each. I checked the ferry schedules and with at least 2 mid day ferries running on each segment I should have 1.5 days to explore each island, obviously not enough time but a good start. I finalized the hotel bookings this weekend and ended up booking Kalergis Studios Naxos at St George Beach and Hotel Pelican for Mykonos, within walking distance from Mykonos town but away from the bars.
Santorini is the main reason for this trip and i’ll have 3.5 days/ 4 nights at the beginning of my vacation. I was able to secure a room at the caldera with view in Fira in a basic but beautiful hotel recommended by Rick Steve’s. I was more than willing to pay extra for the view and it’s still cheaper than most of the fancy resorts that were way out of my price class.
From santorini it’s off to Naxos than Mykonos and than Athens for 3 nights/ 2 full days before flying back to NY.
Stanbr, thank you for sharing your beautiful pictures. I’ve seen some of them before in different forums and they were the reason why I considered adding Naxos to my itinerary.

What are your must sees and does for Santorini, Naxos and Mykonos? Specially inland villages and such.
Stanbr, do you know the name of the island tour in naxos that you mentioned? A tour might be easier with my limited time there.
Also Is Rafina or Piraeus better connected via public transportation to the Syntagma area in Athens?

Thank you!