That sounds like a wonderful trip. On our last visit, we arrived in Greece on May 11 and spent almost a week each on Naxos, Amorgos & Antiparos — ending in Milos. So you’ve picked some of our favorite islands.
On Naxos we stayed right on the sand at St George Beach at Studios Kalergis. We had a ground floor room with a private patio surrounded by lush flowers, just steps from the beach. Great place. No breakfast but it had a little kitchenette. Highly recommend this island. For sunset happy hour, walk down the beach (away from town) to Flisvos Sportscenter where you can settle with your ouzo on comfy couches on their front porch.
We also loved Amorgos. It’s a short ferry ride from Naxos. There are two ports — we chose Katapola, staying at Porto Katapola pension. We had a large room with huge balcony overlooking the busy harbor. The owner, Giannis, is one of those smiling hospitable Greeks who can’t do enough for you. The island had lots to see— lots of walking — rent a car for a day or two. A highlight is the famous Hozoviotissa Monastery built into a cliff.
We went from Amorgos to Antiparos, an even smaller island! Here we stayed at Mike’s Place with the lovely owner Lillian. Not as much to do or see here but a lovely place to relax. We did have a great boat trip — Lazy Day with Captain Ben. Spent the day sailing around Antiparos — good food & drink.
On both Amorgos and Antiparos, we were just the second guest in our hotel that season. The islands were definitely open for business, but quiet. It was a perfect time. All of the places we stayed were amazingly inexpensive, and each island had great restaurants.
If I had to choose between Amorgos & Antiparos for your third island? I’d probably pick Amorgos, if you can stay at Porto Katapola. That hotel really made the island for us.