Dear fellow travelers,
I'm turning 50 in October, my sister and I have settled on Italy to celebrate (she's 56, we're both single and need two beds accommodations). We're experienced travelers and did the "big" stops in Italy years ago backpacking through Europe (each separate trips), so we've been to Rome, Florence, Venice, Pisa, don't necessarily need to go back and wanting new locales. We enjoy road trips, it's not one of our trips unless we get lost :-), so don't mind driving, we've done plenty, know how to drive stick/manual and capable of reading (paper) maps. We like history, culture, good food/drink (no shortage of that here, I know), walking/hiking, museums not critical to see, but like churches and interesting sites. Approximate length of trip 3 weeks leaving around October 7 from Chicago.
We're thinking of doing Amalfi Coast first for better weather, fly into Naples (no car), take ferry and base in Sorrento for approx 8 nights, be there over my birthday (14th). We're considering splurging for this part and staying in nice hotel (w breakfast included) with nice view and walkable to city center. Day trip the AC, Pompeii, Herculeum, Capri, Paestrum, maybe side trip to Sicily (I'm probably getting spelling wrong on some places). Good amount of time, too much? Hotel suggestions in Sorrento (keep under $250 - $300 per night)? I know apartment cheaper, but we want a bit of pampering on this part and fed a nice breakfast to start the day. So this would be approx Oct 8-16. I've seen online Hotel Ambascitori, good/bad, other options? Some suggestions in other posts I've looked up don't have availability for the dates.
Back to Naples and pick up rental car for road trip. I want to go to Bologna for sure, I've read good things about it. There's the Eurochocolate Fest in Perugia Oct 13-22 that might be fun stop for a few hours, maybe stay overnight in area. Trying to decide if go to Cinque Terre (if yes, where to stay?), and/or Tuscany (neither of us got there before,if yes, where to stay?) or where else to go in time remaining. We have no interest in Milan, but may fly out for convenience/better flight options out, unless another suggestion.
Hopefully I gave enough info for feedback. Feel free to offer restaurant recommendations too. Rest of trip is flexible on costs, not super expensive, we'll splurge if we feel it's worth it, but also open to lower cost things.
We haven't booked flights yet, but know need to do soon. We're used to not pre-booking accommodations and winging it or call ahead from the road if we find something. We do plan to pre-book Sorrento though if we do that at front end.
Thanks!