We are staying in Siena for a few weeks and are planning a side trip for 2-3 days to Elba and another 2-3 trip to Arezzo. Any suggestions for places to stay and must sees?
Yes. The Island of Elba. Sorry about that.
Hi again! My wife and I went to Elba in 2019. We got on the ferry at piombino with our rental car (which was a little scary but without real issues). We were on Elba two nights. Our impression was really mixed. The scenery is nice, but the food on the island in our opinion wasn't great. And very few of the Islanders understood English. What we really loved was the town of Capoliveri, but you can find beautiful towns everywhere. If we were to plan our trip again, we would in all honesty skip it for more time in Tuscany proper.
Totally not saying you should skip it, just giving some honest impressions! If you do go, be sure to visit Capoliveri for some amazing views. Can't say we enjoyed our hotel all that much, so I'm no help there.
We have not been to Elba, but we spent five nights in Arezzo in 2017. We enjoyed it but, truthfully, I would be interested whether there might be other more interesting places in Italy you have not yet visited. There are many spots I would put ahead of Arezzo for one of your 2-3 day stays, as in Montepulciano, Volterra, Cortona.
I don't know how long you'll be in Siena, but Arezzo has a big-deal antique market on the first Sunday of each month and the preceding Saturday.