Would you add Rome to this trip or stick farther north?

Save Rome for your next trip. Where are flyin and out of?Are you spending at least a night in Mulsn to see da Vinci’s The Ladt Supper?

I've been to Cinque Terre at the end of October; weather was quite lovely and the towns were less-crowded. Also, I would consider to visit Portofino (stay in Santa Margherita Ligure) and to see the leaning tower in Pisa (en route to Cinque Terre/Ligure).

But, hard not to visit Rome if you're in Italy and you've never been.

Without more details it is difficult to recommend anything. Just a function of how time to spend in each location. Could certainly add Rome. Fly into Venice and come home from Rome is a very doable arrangement. You can catch bad weather anytime but generally Oct is very pleasant. It is our preferred month travel - generally dry and warm. Days are getting a little shorter but not a problem.

If I had 12 days for a first trip to Italy I’d probably do 2 nights in Venice (beautiful, compact, expensive, crowded and touristy. 2 days was enough for me.), 3 days in Florence (check out their 3-day pass for 72 Euro), then spend a couple days in the Tuscan countryside (we’ll be staying in Montepulciano for 3 nights in June with side trips to Pienza, Orvieto and Siena) before at least 3 nights in Rome (one day for the Vatican, one for Ancient Rome, and one to just slow down and enjoy the city.). We’ll be visiting the Cinque Terre and Lake Como as well on our trip and skipping Venice since I’ve already been there before taking an overnight train to Paris to end our trip. FYI Cinque Terre is definitely well traveled and it’s tough to find an Air B&B for under $100 a night, at least in the summer. Bear in mind if you’re set on taking a future trip to southern Italy you’ll likely pass through Rome so it’s really up to you.

You are wise to not try and do everything. Twelve nights = three places, IMO. And thinking in nights, versus days is useful.

3 nights in Venice is nice. You can decompress from travel in this unique city. Fly into Venice if at all possible.

Take the train and spend 4-5 nights in Florence allows time to see the city and perhaps take a day trip by bus to Siena.

Your remaining 4-5 nights can be in the Tuscan countryside. Rent a car to leave Florence and enjoy the hill towns. Rick Steves' guidebook is an excellent help in deciding where but I will say we love Montalcino and have used it for a base. Returning to Florence to fly out is probably the most efficient but unless your flight is late in the day, you might want to put the Tuscan countryside portion of your trip before ending in Florence to avoid the need for a one night stay before flying..

October is generally pleasant on the first half, then as you approach the end of the month it gets rainy, although not cold. End of October and early November is statistically the wettest time of the year, but nobody can predict what will happen when you go.

If you decide to add Rome, make sure you have enough time for all you need to see. The consensus in this forum, is that the ideal allocation of time is:
Venice: 3 nights
Florence only: 3 nights (add one night for each day trip in Tuscany you want to take while based in Florence)
Rome: 4 nights

Since you say you have 12 nights available on the ground, you could add 2 to Florence (so you would have 5 in total) and use some days to visit the countryside or the smaller Tuscan towns near Florence (Siena, Lucca, San Gimignano, or the wineries of the Chianti hills, since you like wine)

The ideal flight arrangement for the above plan is an open jaw multi city flight, flying into Venice Marco Polo Airport (VCE) and returning home from Rome-Fiumicino Leonardo Da Vinci airport (FCO).

If you do decide to save Rome for a future trip, here are some other places that I really liked in your general area. I like Verona very much. From there it is easy to go to Lake Garda, Sirmione is a lovely little town with a picturesque castle right on the waterfront. I very much enjoyed Ferrara, again a castle, great piazza and old town area and you are not going to encounter hoardes of tourists here. If you stay north, Trento and surrounding area is very scenic. The hard part is trying to narrow down so many great choices.

Thank you all for your helpful ideas! I’ll study these more closely. There is of course so much we want to see but we try to not cram in too much and feel blurred and exhausted. Our flights are up in the air depending on the final itinerary but we’re definitely planning to fly into Venice and out of whatever airport is closest to our ultimate final destination. We are not really box ticking people trying to jam everything into one trip just to say, well, we’ve done Italy! That one’s off the list! That’s why we plan at least one more trip there to see the southern part. That’s why I’m a bit torn because it’s hard to go and not see Rome as first timers but I also want time to do it justice.