Where to stay - Capri or Anacapri? Day trip tips?

You might be better using Sorrento as a base. You can enjoy Sorrento for a day or two, and make a day trip to Capri, the Amalfi Coast and other destinations.

You didn't say where you are arriving is it Venice ?
If you haven't gotten your tickets yet, you can depart from Naples.

We have booked flights already - we arrive in Verona, and we depart from Naples!

My guy is set on basing ourselves in Capri after Rome! My original thought had been Sorrento as well, but I gave in. Plus the more I research Capri, the more excited I am about spending more time there!

I wouldn't stay on Capri and plan on day trips....the ferry schedule would be severely limiting for me, beyond a trip to Sorrento and maybe Amalfi or Positano....if he wants to be most relaxed, then spending time in the different areas of the island would be VERY relaxing....

Casa Mariantonia in Anacapri is where I stayed 2 years ago for 3 nights. The hotel is wonderful (family run) and easy to get around. It's walkable in Anacapri and if you want to use buses is easy to get all over the island. My room was one of the larger i have ever had in Italy and very comfortable. We did not use Capri as a base to see the Amalfi, but I guess you could.

As said above, daytrips from Capri to the Amalfi coast will be difficult - you have to be sure not to miss the last ferry or hydrofoil back. There's frequent service from Capri to Naples and Sorrento, but they're not on the Amalfi coast. There's much less service to the actual Amalfi coast towns of Positano, Amalfi, or Salerno. If you take a boat to Sorrento, you then have to take a bus to the Amalfi coast towns.

Moral of all this: before taking any daytrips, check all the schedules carefully! If your bus back to a boat is running late, you may have to find and spring for a taxi - which won't be cheap, if its from (say) Amalfi town to Sorrento.

On the other hand, while many say Capri is only good as a day trip, I've read accounts from those who did stay a few days, and how much they enjoyed settling in and relaxing. In particular, if you take hikes to some of Roman ruins, you get away from the mobs fast. Capri sounds like Venice in this regard - all of the people are visiting the same few places, and if you go elsewhere, you're nearly alone.

We were considering doing a day trip to Ischia (nearby beautiful volcanic island with thermal hot springs) as well as visiting Positano.... I can only hope at least some of those ferries will be operating through early Fall!

Re. the suggestion about hiking around Capri - that is definitely on the agenda! We're pretty outdoorsy. Thanks for the advice everyone, keep it coming!

MsMaroonEsq, I have to agree with others that Capri doesn't make a good base for exploring the Amalfi or anywhere else. The ferries do not run late in the day, have limited runs to some locations, and can't dock in Positano if the seas are rough (true for any ferry any which serves this port ).

Both Capri and Anacapri towns will be very crowded during the day so there is no avoiding that although hiking away from the main areas will help. We stayed 2 nights on the island, did some hiking, and enjoyed it very much but wouldn't have chosen that location if intending on day trips elsewhere. Sorrento is a better base for that, and affords different opportunities should you have a rainy day.

Current (may change for fall) ferry schedules are here:
http://www.capri.net/en/ferry-schedule?from=ischia&to=capri

For what it's worth, we stayed in Capri for one night in May at Hotel Della Picolo Marina. There was a young German couple who were staying there for five nights and had been hiking all over the island. They had taken an early ferry to Sorrento one day and took the bus round trip up and down the coast. The weather had been too rough for the Blue Grotto for four days, and we connected with them (through the front desk at the hotel) on their fifth day and spent the afternoon on a private 3 hour boat tour of the island with "skip the lines at the Blue Grotto." A spur of the moment decision for us, but it was a glorious afternoon. They were leaving from there to stay on Ischia for a few days.