First trip to Italy itinerary help!

We like to walk and explore and would like to stay away from all of the very touristy areas and would rather live like the locals. We'd like some time at the beach?

Unfortunately all of the sights you mention will be very very busy in late May. They are some of the most touristed locations in Italy. Rural Tuscany with a car will not be bad. With the time you have try to narrow it down to three maybe four locations. Whatever you choose it will be a great time.

Welcome to the forum!

16 days is a nice amount of time but just as you suspect- you probably have too many places.
Count your trip in NIGHTS- so how many nights do you have on the ground in Italy?
Each time you change location you lose at least a half a day- keep that in mind.

A 2 night stay is really only 1.5 day in location.

BTW the beaches in New Jersey far surpass any beach in Italy, I wouldn't make a beach day priority in Italy.

I'll give you what I think is the minimum number of nights needed for each of your locations- then you can decide which location can be cut.

Fly into Venice easier to fly IN than OUT of.
Venice-3 nights
Lake Garda- 2- 3 nights
Cinque Terre- 3 nights- because of the time it takes to get there
Florence- 2 nights if art is not your thing
Tuscany- 3-4 nights - ( could day trip to Florence - but not with car! Florence is a good place to pick up your car and head out of town)
Amalfi Coast- Positano- 4 nights- again because off the time it takes to get there
Rome bare minimum would be 3- but if you really are not interested then 2 can work. (All of Rome is an historical site ) If you come from AC it will take til later afternoon to get there so 2 nights really only 1 day here.

Fly home from Rome

So that's 19-21 nights.
Both CT and AC will be slammed with tourists- I'd drop one of these. And I'd probably drop Lake Garda as well. Visit just 1 "water" location.
Tuscany is probably the only place you can really get away from crowds a bit. Might prioritize that area with a car. Pick 2 bases- one near Siena, one near Montepulciano and give each base 3 nights.

Be careful with the wine tasting you will need a designated driver. Also need to do homework on driving n Itay but that advice can come later.

Most of the places on your itinerary are in very touristy areas! Wine and food won't be a problem.

If you're not into historical sites, there's really not much point in spending any time in Rome. Maybe spend a few nights in Verona instead. Light on historical sites, but outstanding food and wine. Honestly, I would take Lake Garda off your list. It's pretty, but IMHO, not in the same class as your other choices.

You could take a train from Rome to Salerno, and use it as your base for visiting the Amalfi Coast. Salerno is your best chance at living like a local.

We were just in Sorrento/ Amalfi Coast this past May, and were actually disappointed in the area, to be honest. The lack of infrastructure and the resulting congestion resulted in no efficient or quick way to get anywhere, whether using public or private transportation. Things just don't work well, and northern Italy shines in a comparison.
We found the regional trains ( Naples, Pompeii, Sorrento) in Southern Italy to be erratic, SRO, and without air conditioning. The trains were kind of on time in the mornings, but ran later as the day progressed. We used a private driver on the Amalfi Coast day trip, but still sat in congestion on the roads. And- the crowds, even in May, which from reports, are repeated in the fall. Shoulder season isn't much different than high season, crowd-wise. Positano was packed with tourists shopping in the same high- end stores that are everywhere. Amalfi town was shoulder-shoulder people on the main drag- and again, this was May.
Perhaps if we were better versed in the realities on the ground we wouldn't have been so disappointed. We had just left the calm and beauty of Lake Como, and wish we had stayed. We are seasoned travelers, but missed these very important details. I'm afraid the area has become a victim of its Instagram success.
In reading reviews after our trip, I think recommendations to train and stay in Salerno would have been an improvement. Then perhaps ferry to Sorrento? However, the ferries are very weather- dependent.
Also, if the weather is bad, which it was for some of our trip, there aren't many indoor options for entertainment.
I'm glad we went, especially to Pompeii , but I have no need to return to Southern Italy. I'm wishing you a better experience. There is a wealth of info posted here on the Forum, as visiting Sorrento/ Amalfi Coast is a weekly topic. Safe travels!
https://community.ricksteves.com/travel-forum/trip-reports/venice-lake-como-sorrento-amalfi-coast-with-lots-of-rain

PS
You also are pretty late to the game lodging-wise. Many travelers book the AC 8-9 months out- those crowds are sleeping somewhere! Lodging availability may influence your itinerary.
Good luck.

Sounds like you have 15 nights and 14 full days. To experience places adn things you cannot do at home consider the following.

Spend 4 nights and 3 full days in Venice and roam the areas away from Piazza San Marco and the Rialto Bridge. Just take walks, Rick has some in his book and if you can find it, get a copy of "24 Great Walks in Venice" which will guide you to out-of-the way calles. find cafes, have coffee, admire the architecture. Include a trip to Torcello, far out in the Laguna where Venice was first settled. This will get you away from the crowds. DO consider a dawn walk to Piazza San Marco when the tour groups have not yet arrived. After dark it is magical as well.

5 Nights and 4 full days at the agriturismo. This will be a restful centerpiece for your trip. Depending on how far you want to journey for day trips and exactly where the agriturismo is, you might be able to visit the beach in Tuscany. Make sure you can park and ride the train or a bus to get to Florence for your day trip. Parking nightmare and driving disaster zone.

3 nights, 2 full days in Liguria, but NOT the Cinque Terre. Consider Camogli or Santa Margherita Ligure or Rapallo for a less-touristy experience but plenty to explore. You can day trip to the Cinque Terre if you like.

3 nights, 2 full days in Rome. Another great city to wander and get into neighborhoods where real Romans live, if historical sights are not your thing. So atmospheric! Consider staying in Parioli, a nice Roman upscale neighborhood near Villa Borghese, or in Prati, the other side of the Tiber but don't stay near the Vatican. Stay north of there. This is another upscale Roman neighborhood. Consider a daytrip to the coast at Sperlonga or Ostia Antica to see an Italian beach scene off-season. Seriously, no one will be there! There is also a "24 Great Walks in Rome" book I highly recommend. Should be available used.

Ciao!! Ditto what Lauren said..that is a lovely..less touristy..if that is possible..itinerary..all of the above advice is excellent..however. I am a big fan or the south but the infrastructure is just not there for a first time visitor. I also would consider a train as much as possible and getting a driver to your day trips. Totally agree re Santa Margherita..one of my fav places..have been there 8 times for lengthy stays..as there is a VERY convenient train station..5 min to Camogli..and if u must go to CT..u can do a day trip or take the ferry out of Santo Margherita..super easy..right in town. I do enjoy Venice..for a half day trip or so consider the 25 min train to Padua..less touristy..beautiful. then you Tuscan part..I love the above idea of centering your stay..your agiturismo can assist with transport to small villages. Lots of good info here from seasoned Italy folks!! Remember..what u see and experience you will love..you will NOT be disappointed with what you did not see. I know your trip will be wonderful!

I would suggest staying in northern Italy and skip Rome and points south. Is there a reason you have especially flagged Positano? Nice, but.... I have been to Sorrento pre-covid in Nov. I loved it BUT getting there even pre-covid was a pain and the bus to Positano was an experience in not getting car sick.

I would focus this trip on northern Italy.
Fly into Venice and stay 4 nights minimum. Wander and wander but, even though overpriced, get a drink and pastry at one of the cafes in St. Marks square. Take vaparetto rides and get off wherever.

From there go to Tuscany for your 4-5 night stay in a agriturismo. Although I am Rome averse, I LOVE Florence so I would highly suggest staying there for a few nights. Florence is nothing like Rome. Stay a 2-3 nights.

From there, I would go to Garda or another lake for the remainer of your time before taking the train to Milan for an overnight before flying out.

I was last in the CT early 2000s, pre flood and pre cruise line excursions. The area was not the mob scene it is reported to be today. Although the area is stunning in natural beauty, maybe stay nearby?

Have a great trip.

Hi and welcome to the forum, jerseygirl!
To echo the others, you have too many locations on your wish list, and nearly ALL of them are tourist magnets. As well, you won't be "living like a local" without the language or being able to settle into one location for more than a few days; you'd need months if not years for that.

That said, Laurel has given you a lovely itinerary that will place you in less visited towns and neighborhoods. As an American who has had the rare opportunity to be a resident of Rome for a number of years, her advice - based on that firsthand experience - should be given serious consideration, IMHO. :O)

Avoiding the CT and Positano/Amalfi Coast is especially important if wishing to avoid the masses.

She mentioned the Prati area in Rome? We stayed in that district and number of years ago and enjoyed it very much; it's just far enough removed from the major tourist attractions to feel more residential but you can still walk all over the historic center from there, as we did, if up to expending the shoe leather. It's a city best experienced on foot anyway. And even if not "into the historical sites" I'd at least make a point of viewing some of them externally 'cause it's sure not stuff you're able to see at home.

Thank you everyone for your input! Looks like we'll have to reassess!