Help with 2 week itinerary

Hi Renee. Just 1 opinion, but yes, go to Venice, if even for a day. People have mixed feelings, but it is unique; since you are so close, you should go. When leaving Rome (day 4 or maybe day 1 or 2?) take the train all the way to Venice - in 4 hours you're there. Then work your way back to other destinations. Enjoy your trip!

I will admit I was very iffy about going to Venice when we were planning our three week trip (currently in Italy in Florence), and I am really glad we went for two nights. Venice is very unique and you can really see the highlights in 1-1.5 days. Do the touristy stuff near St Mark's Square and then just wander the streets away from that area.

Sorry, but how many floating cities teleported from the 18th Century have you already visited in your life? That's what Venice is behind the crowds at San Marco and the restaurants for tourists: a time-machine.

You could fly into Venice and depart from Naples. The High speed trains from Venice to Salerno stop in Florence, Rome and Naples.

I wouldn’t skip Venice- there is nowhere else like it
Fly into Venice and give it 3 nights

Will you have a car while at Tuscan agriturismo? Likely necessary

We spent 9 nights in Amalfi area but that was the focus of our trip. Not sure how relaxing your time there will be, especially in July heat and crowds.

Looks like you have 14 or 15 nights? Hard to tell. Count your trip in Nights rather than days, gives you a better picture
Each time you change locations you lose at least a half a day- checking in/out, transit to/ from, getting oriented.
A 3 night stay means just 2.5 days of sightseeing and you arrival day will be a jet lagged blur.

4 locations in “2 weeks” is almost already too fast paced so you might reconsider - choose Tuscany or Amalfi for a more relaxed time. (On a first trip I’d drop Amalfi )
Do keep in mind it will be wicked hot. Make sure your accommodations have AC!

Having just come from Amalfi, I would definitely swap Amalfi for Venice & Verona.

I don't believe in "musts" in general, but watching Tucci last night makes me want to go to Venice myself! Just an idea of how you might get some coastal relaxation time in but still have time for Venice (assuming you cannot add days): add Venice between Rome and Florence, and then choose somewhere coastal in Tuscany. The Amalfi coast is going to be absolutely mobbed this summer--all the coast gets busy in July, but the southern Tuscan coast is gorgeous and you'll be surrounded by fewer international tourists than you will at Amalfi.

Well, I guess I'm alone as a counterpoint, but we just did a trip in which I felt we couldn't miss Venice and we went from Rome up to Venice and then back to Cinque Terre. I don't think trading a day somewhere else for a day in Venice is a real thing. It's trading a day somewhere else for a day of travel and a little time in Venice. Even if you stay a couple nights, it would only really be a single day on the ground there. Venice is amazing, but so is the rest of Italy and I wouldn't trade 3 days somewhere else for 1.5 days in Venice.

Thank you @sleight. I was questioning everything. While this is our first trip, the plan has always been about relaxing in Tuscany and spending time on the Amalfi Coast, with some sights in Rome and Florence sprinkled in. It was never meant to be a whirlwind tour to squeeze in as much a possible. We want to meander a bit: stay too long at local vineyard, take a private boat along the coast, and have a little touch of Il Dolche Far Niente after the madness of the last 2 years. It's about reconnecting with each other.
Maybe it will be an excuse to bring the kiddos someday...

Your itinerary looks great. We have been to Italy 3 times and still have not made it to Venice. It’s your trip and you get to go where you want. 6 days in Amalfi is not too much. There are lots of places to explore.

Now do I want to go to Venice? Most definitely! Another trip!

So many choices, so little time! Venice is my most favorite city and I try to do time there on every trip. It is so magical, especially getting off the main tourist routes and into the neighborhoods. Venice Lido does have a nice beach, probably be less crowded than Amalfi in July. Venice area has much to see and do. I find it's a great place to recover from jet lag and ease into my vacation.

If you haven't bought airfare, consider flying into Venice and leaving from Rome. Venice, then Florence, Tuscan Agritourismo, Rome. You will break up time in a big city and your relaxed time.

Whatever you decide, it will be a great trip!

My wife was hesitant about going to Venice and a number of our well traveled friends advised against it but we loved it. Nothing like wandering around looking for cichitti's at the various bars (little appetizers, a bit like a wandering happy hour with tiny bites). And then there's the magic of the dueling orchestras at St Mark's Square, an amazing experience. Plus if the crowds get to you all you have to do is wander a block off the main path and it gets nearly deserted.

https://firsttimetoitaly.com/venice
https://theromanguy.com/italy-travel-blog/venice/where-to-eat-the-best-cicchetti-in-venice/

Your going in July which is going to be very hot, I would cut Florence and go to the Alps. Florence sits in a bowl at the foot of some mountains, cold and windy in winter and hot in summer. The alps might have some rain in July but they will be pleasant and green. A must for me any and all trips to Rome is the Gallery Borghese, and go ahead and do Saint Peter's twice (or a million times, that works too). J