We are going to cobble together an Italian trip, 10 to 14 days in mid October and want the biggest bang for our buck, and time. Several days and lots of Rome is a given. Then what? What did you love?
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Don’t try to pack in too much so you only get to experience it like in the movie Vacation.
If you’ve never been, I’d devote the remainder of your time between Tuscany and the Ligurian coast. Specifically, I’d plant in Sienna and day trip from there. Then I’d plant in Camogli, Chiavari, or Sestri Levante, and day trip from there. Those towns are ones that tourists typically only day trip to from more crowded, touristy cities like Florence and the cities in Cinque Terra. Certainly those are both worth seeing, but the places listed above are magical after tourists leave.
I also love the off the beaten path areas of Venice, and the Dolomites are spectacular. If either speak to you more than Tuscany and/or Liguria, I can give recommendations there too.
The bottom line is this probably won’t be your last trip to Italy once you experience it. 
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14 days and mid-October are both excellent starts. It really boils down to what you want to do AND enjoy. Of the more touristy places, I am not a fan of Rome but both Venice and Florence have their charms. Milan could be a hit or a miss depending on what you are into. But the lakes region north of Milan is quite possibly one of the most beautiful regions I have ever been to.
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For our honeymoon in September/October 2006 we flew into Rome and spent 3 nights there in a small BandB by the pantheon. We loved Rome and saw all the city sites and enjoyed the food. Then took the train to the Amalfi coast. I recommend staying in Amalfi for easier access to travel. We stayed somewhere along the coast but were either stuck at our hotel because the busses were too full and would pass by or pay for a taxi like $25 usd each way back then. We did about 4 days there and saw so much from the Mediterranean, Pompeii, the beautiful small towns and the amazing lemons.
We got back on the train to Florence and rented a car. We didn’t stay in the city any longer. My H isn’t a museum guy and we saw so much in Rome we were ready for peaceful country side. Our apartment was in Greve in Chianti for 5 days just lounging around the town square, walking by farms/groves, driving into other Tuscan towns and we loved buying pasta, sauces, breads, and produce from local shops to cook in the apartment. This was our favorite part of the entire trip.
We turned the car in and got on the train to Venice where we rented an apartment for 3-4 nights, can’t remember. I hated Venice, it’s too expensive, touristy with terrible food and this was before cruise ships took over. We did a day excursion to north Italy to see the Dolomites and wish I had stayed there instead, it was so beautiful! We flew home from Venice airport. I feel like I really got a good taste of Italy and if I can travel to Europe again would choose a different country to see.
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I’ve been to Venice 3 times. The secret is where you stay and what you see while there. The Dorsoduro behind the Academia is a wonderful neighborhood, with a transcendent little wine/chicetti bar called Schiavi. If you go to Venice, stay away from the heavily traffic areas and spend your time in the sleepy sections of town.
That said, and I LOVE Schiavi, I’d choose Cortina, Canazei or Ortisei every time. It really depends on how much you love the mountains.
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We wandered all over Venice and certainly worth seeing but 2 days would have been plenty for me. Our apartment was away from the tourist areas. We did have to walk on platforms for much of the time due to flooding which honestly I didn’t mind as much as the prices for food. This west coast girl loves mountains. Our day trip stopped at a working farm and they served us the most amazing cheeses and salami type meats I’ve ever had and had since. I was 6-8 weeks pregnant by then and so much pork everywhere made it so I couldn’t touch it the rest of my pregnancy but that salami didn’t affect me! I don’t remember the name of the town in the north we visited. It has bronze statues all over the main road, very charming. The shop people would speak to me in German thinking I was a German tourist rather than the obvious Americans (or Brits) we were everywhere else. You must have been there many times, I’d loved to see more of the country but had to cut somewhere. There was a fresh water fishing trip in the countryside near Venice that was the last thing I cut out.
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I just googled it and it must have been Cortini! Thanks for jogging my memory.
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Tuscany in the fall is beautiful……
Montepulciano - need I say more?
Pienza - Really beautiful town with many buildings from the 1400’s, where Romeo & Juliet (1968) was filmed
Siena - fabulous architecture - famous for the Palio race.
Florence
Verona - great vibe in this city, great sight seeing, Roman amphitheater (still used for opera), and of course Romeo & Juliet scene
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We’ve been to Italy 4 times and Sicily (that was a separate 2 week trip). We don’t enjoy hopping around and try to pick places where we can stay for 3/5 nights and dig in to an area with day trips.
On our last trip we visited Bologna/Modena/Parma and it was not long enough. Plenty of small towns and great food. On an earlier trip we hiked in the Dolomites, visiting Bolzano and Castelrotto. Really lovely.
We also stayed in an agristurismo outside of San Gimignano, which was a great location for side trips to Sienna, Volterra, and other smaller towns.
We did rent cars on these trips so we could get outside of the larger cities. Plus we had our girls with us and that was easier than trains.
We also enjoyed flying into Venice and out of Rome.
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If northern Italy is of interest, then Lake Como and Bergamo are two of my recommendations. Add Cremona if you’re into in classical instruments.
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I cannot believe no one has duggested the Amalfi coast! Possibly my favorite place on earth. I’ve only been once, 20 years ago, but also in early October. Weather was perfect.
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I’ve been to Italy 3 times already, my suggestion is not to crame to much in one trip. My husband and I actually loved Milan too, have passed through Lake Como on the way to Switzerland, our plan is to go back someday but COVID happened.
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Florence but stay out of the city center, assuming you’re in relatively good shape and can handle a 10-minute walk tp the main sites. Day trip to Tuscany. We did a Rick Steves-recommended trip that was amazing.
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Maybe you could tell everyone a little bit about what you like and what you like to do on vacations. Italy is a big country in the sense that areas are very different from one another and Sicily is a world unto itself ( great place, btw).
Also, most Americans go to the touristy places, but if you like to see things and have fewer crowds you can find places that are just as beautiful and often are cheaper. And the food is authentic as opposed to what a tourist would eat.
For that amount of time, I’d pick three places maximum. Any more and you are just spending most of your time moving around. For a first trip, I’d suggest flying into Rome, driving down the coast to Pompeii, and Herculaneum and then deciding between spending a few days in the countryside ( not Tuscany) and maybe flying out of another city (Genoa/Milan). IF you are adventurous and love art/architecture you’d build a different trip than if you want to spend time visiting vineyards. Think of what you want to do then build your trip on that basis.
Rome should not be missed, nor should Florence. But do both and that’s at least a week. So given your itinerary maybe chose one and then spread out.
Stay away from American guidebooks/Rick Steves videos etc unless you like that type of trip. Those places are filled with folks from CA 
which might be what you are looking for. And if you are, that’s great too.
Thinking of hiking? Don’t miss Bergamo and Bolzano many Europeans have discovered these areas but they get fewer visits from Americans. And if you are South of Rome, there are lots of places to explore.
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Lots of pickpockets in the cities - constant vigilance! (But a beautiful country)
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The train station has a lot of people pretend to help you with your luggage, especially if you look a bit lost, don’t fall for that scam.
When I travel, I always have a purse with proper lock over it except in England, nothing happened to me.
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Hire a private tour guide for a day in Rome, especially one who knows the Vatican (don’t miss!). Then explore by foot. At least a week.
Lots of charm between Rome & Florence. Sienna is a great base to do bike trips from.
Florence. loved. At least a week.
Venice? ehhh. 2 days max. If you have to cut any place, I’d ditch Venice.
Pisa: SKIP.
I do look at the Rick Steve’s books—and then avoid those areas.
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Usually, I’m all for skipping tourist traps. This is an exception in my book though. There are people EVERYWHERE, but there is open space around the tower where the public can’t go. You will get a good view. It’s like seeing David in person, or the Eiffel Tower. There’s nothing else like it, and it’s worth it to do it once. I say that if you’re in the area, say traveling between Tuscany and Liguria. I wouldn’t go way out of my wat to see it.
If you go to Florence, the market is great. Take the tour to the top of Brunelleschi’s Dome. Fabulous views, and more interesting than just walking up the tower.
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We’ve been to Italy several times over the years and have loved it all. My suggestion is to figure out what type of things you’d like to see on this trip as a starting point. Roman ruins? The coast? Medieval hilltowns? Museums? A place less trafficked by English-speaking tourists like the Adriatic side? Large cities like Florence and Bologna, or more rural?
One way to start narrowing things down is by viewing travel videos. You can find many online or at your local library. Rick Steves offers all his shows free on his website. Samantha Brown. Others on PBS. Many travel videos on Youtube (quality varies depending on who made the video).
Then, since you’re going to Rome, I suggest picking at most 2 other destinations. Keep in mind you lose about a half day each time you change places when you think it thru (finish packing, check out, go to train station, travel to next place, check in to hotel). If you can, go for 14 days. The flight cost is the same but you amortize it over a longer trip.
You don’t need a car in cities but it can be convenient for Umbria/Tuscany; if getting a car be sure to look up areas restricted to locals (called ZTL) so you don’t get expensive tickets. Some of our favorite places were found thru serendipity; going for a drive in Umbria or near Bari, seeing a place off the highway or road, and deciding to go take a look.
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Yes!! You will have to pay for tickets in advance but you/your group will skip the lines (often long) and not spend time trying to find things. Worth every cent. Also go to busy places like the Vatican early (private tours often open at 7AM). You’ll beat the crowds and enjoy the early morning.
That’s pretty much what I’d do too !!
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