Some Santorini and Naxos questions

Santorini- walk down to Amoudi Bay in Oia for a waterside meal at a fish taverna.
Visit Akrotiri, the ancient site.

Buy the tickets on Naxos while you're there. It's best to buy in advance so you can avoid a line. You'll probably walk past the ticket office at least a couple of times while you're there.

My hotel arranged a driver to get from the ferry pier on Santorini to Firostefani (the outskirts of Fira). It took nearly an hour - in mid-October. Maybe you can go by boat to Oia from the ferry pier.

If you walk past the fish taverns in Amoudi Bay below Oia, you will find some rocks that people swim off of. It is a little rough getting there but worth it. The four young adults all jumped off the man made cliff. I went in the water while my husband and his brother stayed dry. Your young adult daughters will love it!

And if you like hiking, walk from Oia to Fira and then take the bus back. It is the most beautiful hike I have ever taken. It took us about three hours with lots of pictures. The first part from Oia is a hike with rocks and somewhat rough terrain. About half way, you walk the rest of the way on a sidewalk.

Thanks All for the great recs! Since we are flying to Santorini, then Ferrying to Naxos .. not sure if we should buy the tickets online since we wont be at the pier before hand? Not sure if you can easily buy them in Oia?

Sorry, I misread your plans. I bought my ferry ticket in Fira. The office was on the main street. (Each ferry line has its own office). You'll still want a private transfer to the Santorini ferry pier.

I used this website to find ferries. Choose the sailing you want and google the ferry company to find their offices on Santorini. They are probably all in Fira, but you'll be in Fira at least once while you're in Oia, surely.

I also took the ferry from Santorini to Naxos. I bought my ticket online when I was in Athens, but then I got instructions to go into the ferry company’s office in Fira, to turn my online transaction into an actual ticket, which I did the day before the ferry trip. So, I’m not sure there was any benefit to buying online in advance. The ferry was not crowded, in mid-June of 2017. The trip was a pleasant 2.5 hours, after waiting quite a while in the pier area before being allowed to board. And yes, there is some time and expense involved in getting from your lodging to the ferry pier.

I purchased our tickets online ahead of time via the Champion Jets website. That did need to be converted to an actual ticket at their office on the island. Unfortunately for us, there was a one day strike on the day of our sailing, so we ended up having to fly to our next island. STEP warned us about the strike one day ahead of time; the ferry company gave NO advance notification about it. Once we were back home, I requested a refund and Champion Jet was very prompt in issuing that.