First Time Visitors- Looking to avoid the typical crowd favorites

One resource that we've found to be particularly helpful is the guidebook "Backroads Italy" from DK publishing. It's full of off-the-beaten-path excursions and locations that you'll not find in other guides. Though it's geared towards independent travelers with a car, we've found that much of the information is of interest to those traveling by rail too. The guide is a terrific planning tool for independent travelers who want to explore a bit further afield than the usual tourist..
There's another called "Backroads Northern Italy" that we used on our last trip to Tuscany and Umbria which is also quite good.
You can find used copies on Amazon for just a few dollars.

I think Umbria and the Ligurian Coast are beautiful areas that are relatively little-traveled by US tourists. Puglia is getting increasingly popular, but it's hard to get to.

BLQ is a better airport than FLR.

FYI vis à vis "these were recommended by Chat GPT"
ChatGPT produces CO2 equivalent of over 250 transatlantic flights monthly, study finds
https://www.emergingtechbrew.com/stories/2025/01/16/chatgpt-co2-knownhost-study

As it's your first trip, allow time to accustom yourselves to being in Italy - it's an easy place to be but everything from eating in a restaurant to using transportation will still be quite different. Assuming you'll be jet lagged, count on 2 days minimum in Rome. I love Chiavari as a place to be, but it lacks significant landmarks that attract visitors. Livorno lacks both the classical aspect of Italian cities and significant attractions due to bombing in WWII and I would skip it. Lucca would be a good choice and nearby Pisa airport is also better than Florence airport.

Are you planning to rent a car?
I have stayed in Orbetello and toured the area twice. I’ll first note that it will be very hot and buggy, just making sure that is okay. It’s a summer family trip area and full of lovely beaches, great seafood, plus there are many pretty hill towns in the vicinity and many Etruscan sites. Car needed.
Chiavari area would be nice, very typical seaside with day trips close by. No car needed.
Livorno is larger and I think probably not exactly what you are looking for.
For any coastal place, you need to start looking at accommodations asap.
I suggest you skip AI and use a book or vetted website.
I would pick just one base, especially in summer there is no need to move around that much.

I know the Cinque Terre has got to be jammed this time of year, but I feel like most places will be anyways, especially so on the coast. So, maybe that’s still a decent choice? I agree you probably need to take a step back and check out a few books. You have to be a little careful about that too, because some books seem to try to make every place sound interesting. Italy is jam packed with worthwhile sights, and it feels like ChatGTP is working way too hard. There’s a happy medium between places like Florence/Venice and these real “not in the travel book” places. Florence too much? How about Lucca? Venice too much? Padua, Verona and Vincenza await. You’re first timers too. Don’t let yourself get scared away from the bigger/mid cities. It sounded like you have 9 nights? If you split that into 3 stays that’s a decent amount of exploration with being too rushed.

Have you watched the travel videos by Stanley Tucci and Alex Polizzi? You'll get some good ideas

All of the comments have really helped me refocus the trip- I appreciate all of the help! I have engaged with two different travel companies- JayWay and Vagabondatravel- I may just be in too far over my head to make all of the plans for such a trip- It may be worth the extra cost considering all of the time already spent and getting nowhere--

Go to the “Our Tours” section of this website, then look at the various Rick Steves’ tours that include Italy. Rick Steves covers the most important places in Italy for a first time visitor. Obviously in 10 days you can only cover so much, therefore try not to go too far from Central Italy since Rome is one place you need to be,

Rome is by far the largest airport, so you might find that the best flight solution might be flying in and out of Rome, depending on where you come from? By the way it would help to know where you are writing from and which your home airport is. In this forum there are people asking questions from all continents. with the possible exception of Antarctica, but I’m sure sooner or later there will be a question from a penguin willing to visit Italy at some point.