First timer's trip to Italy for two weeks

Also side note, does anyone have any experience with use of Airbnb in Italy. Found a charming apartment in Positano for our 6 nights there but have never booked through something like this before.
https://www.airbnb.com/rooms/1609381

Congratulations! I have no experience with airb&b but many others here do. I travel on a budget, so my hotel recommendations are generally inexpensive.

I love the idea of spending a chunk of time on the Amalfi Coast. After Rome it's my favorite place. Be sure to visit Ravello, some of the other towns on the coast, if you can get to Paestum it's a great place (perhaps you could squeeze in an overnight). In Paestum, I like Hotel Poseidonia Mare, they will pick you up at the train station, loan you bikes. Paestum has mozzarella farms, a nice beach, a very good small museum, and the archeological site.

In Naples, I like the family-run B&B Sweet Sleep, a few blocks from Napoli Centrale (easy walk with luggage). There's a rooftop terrace with a hot tub and sauna. Look at photos and reviews on booking.com.

In Rome, if you like breakfast served in your room, Hotel Teatror Pace is just a street away from Piazza Navona.

In Florence I like Hotel Bigallo, just around the corner from the Duomo.

I use airbnb a LOT - all over US (Boston, San Fran, San Diego, LA and more) and Europe (London, Bath, Paris, and other places) including in Venice, Florence, Rome and Atrani (near Amalfi). I've never had issues - used it for both apartment rentals as well as rooms where the person was there.

Always always read thru the reviews and make sure that people aren't complaining about cleanliness or noise or too cold/too hot. I always make sure it has the amenities I want (wifi, parking if you will be renting a car, which floor is it on and does it have an elevator, ac, laundry if you want it) and I also try to use the street view option if it is there to get a feel for the area. The one downside is meeting up with the person. Sometimes it can be a pain in the butt. I try to tell people within a few hours when we hope to arrive, and a lot of people have different schemes for giving people keys and whatnot...but you can feel like you are being hurried if you know someone is waiting for you to show up - things can happen that delay you and I hate the feeling of knowing someone is sitting around waiting and you are delayed (because I hate sitting around waiting). I could tell you a few stories, but I won't go into it... But we have had some amazing places - the apt in Rome with views of the Colosseum for $150 a night (Canadian) - you'd NEVER get that price for a hotel that was half as nice as this apt was.

My tip - hopefully you are a morning person...even if you aren't, force yourself to get up early and go out (even if only for an hour then go back to your room/apt for breakfast). I tell you, there is nothing like Venice at St Mark's Sq at 7am with maybe 15 other people there (as opposed to the 1500 that will be there at 10am)...Rialto Bridge almost devoid of people, no fighting elbows to see the Bridge of Sighs. Or in Rome (we stayed very near the Colosseum) to wander over to the Colosseum, or to wander around Amalfi (or whichever town you stay in) with the sun coming up over the water...

We used Sorrento Silver Star car tours for a private day trip around the Amalfi coast - 8 hrs...hitting Ravello (my fav - make sure you spend a day here!), Sorrento and Positano. They will tailor the day to what you want to do. We used Walks of Italy for a tour of the Vatican (after hours) and they also offer food tours and whatnot in Venice, Florence, Rome...I was tempted to do one, but passed.

We've almost always gone over mid-Sept - we've always had almost perfect weather - hope you have a blast!

OMG - I was checking out the airbnb listing - that looks amazing - the view melts my heart! She looks like she is already booked for much of Sept tho, so unless you are going to be there at the end, you may be out of luck...otherwise, you'll have to decide and book soon before it's gone! Also - when you book airbnb, you do have to pay right at the time of booking - I know it sucks to be charged when you are still so far away from going, but at least it's paid for! Make aure you check out the cancellation polices - some are very strict and will issue NO refunds if you cancel...some may refund half, some may refund all - just be certain of you get a place with a strict cancellation policy...

That listing will only give a 50% refund if you have to cancel...

I would take away one day on the coast and add a day to Rome, I find it to be such a romantic city and just has this wonderful Eternal City vibe. There is a lot to see and a lot of walking so I think four night would be better.

Thank you for the practical advice. The only thing that concerned me about an airbnb, besides the cancellation policies, would be not having the local advice regarding sights and restaurants of hotel staff. Still need to choose accommodations for Venice, Florence (or may stay in Siena instead), and Rome if anyone has any recommendations. Budget is approx 100-250 a night.

Got your private message (I'll reply when I have a few more moments)...I just wanted to respond to recommendations about restaurants and what not - a lot of the airbnb's I've stayed at have had info on what to see/do/eat/shop nearby. The one in Atrani had a binder with all pertinent info including where to get some groceries, transportation, suggestions for restaurants, what to do with the garbage - actually, I'm sure the Rome and Venice ones did as well. And the owners are generally more then happy to give recoms. I would imagine so many of the people staying with them ask these things, they have the info all set up - you shouldn't have any problems there :)

I think your schedulle looks perfect the way it is. If you've dreamed about going to the AC since you were a young girl, do it! I would not change the Florence portion of your trip to stay in Siena. IMO Florence just has so much to see, explore and enjoy, and Siena is a nice place to spend an afternoon. I took a day-trip from Florence to Siena and was very happy that I'd chosen to base in Florence.It's pretty, but the HIstory/Art are in Florence.

As far as airbnb, I am going to Italy and Germany in May and have booked 3 of my places at airbnb. I do want private bathrooms, which I have found. All 3 hosts have responded quickly and have offered helpful hints.

The best is that all were 70-80 Euros a night for 2 people! And very centrally located.

Good luck!