Venice, Florence and ??? (UPDATE)

Padua is nice and not too small, good train service. It is, however, very close to Venice and daytripable from there if you want to just extend Venice to 6 or 7 nights.

Lucca is close to Florence but feels a world apart. Small, not too small. Good train service to Florence and Greta pedestrian area.

Look at Vicenza. Padua, Vicenza and Verona are all easy day trips from Venice but they’re all also nice places to spend a couple of nights.

We did Vicenza on the most recent trip and the architecture is incredible. There’s quite a few Palladian villas to see. And Vicenza has the Teatro Olimpico - which is worth the trip in and of itself.

I have a nice guide we used who will walk you around for a few hours, showing off the Palladian architecture.

I really liked it there. Padua was great on this last trip as well for Scrovegni Chapel and a tour of the university but it’s Vicenza that has stuck with me.

I can suggest a slow transit from Venice to Padua....a barge down the Brenta Canal...but you would need to confirm dates for late October. https://www.ilburchiello.it/en/tour/ It makes a couple of stops at Palladian estates, goes through canals, sees a part of Italy we often miss.(but in full confession, I haven't been back to Italy since I learned about it. I just keep
Dreaming about it.).
Bologna is also enroute to Florence and either enjoy the city itself, or use it for some day trips to foodie or car buff locales. Parma for ham and Parmesan, Modena for balsalmic Vinegar. Both Ferrari and Lamburgini have museums nearby and if you got interest and money, you can drive them. I think that woild be fun (and yes, there is a copilot)

Padova: https://tinyurl.com/ycb5euy3

The Scroveni Chapel is in the Musei Civici; the entire complex meriting exploration. Town also has the Prato della Valle, the largest square in Italy; one of the largest in Europe.

Rome is likely the city where you will fly in or out (or both), being the largest airport, so Rome might be in your future, whether you like it or not. Venice has some options to North America, but mostly seasonal except for JFK (with Delta), which is year round. Florence has no flights to North America and the closest intercontinental airport is indeed Rome. So you might as well include at least your last 3 nights in Rome before coming home. If you can't fly to Venice directly and you can only find decent flights in and out of Rome, you can always reach the either Florence and Venice from Rome airport by high speed train (2 hrs to Florence and 4 to Venice), and I would do so as soon as you land, if you land in the morning or early afternoon.

Assuming 14 nights on the ground in Italy you could split them into (the exact allocation up to you):
4-6 Venice
4-6 Florence
3-5 Rome
Always leave the city you depart from for last. If that is Rome, spend your last 4 nights in Rome.

Tuscany has lots of nice villages you can visit, many within 1 to 2 hours by train or bus from Florence (Florence is Tuscany's capital city and main transportation hub). So if your husband is interested in smaller towns too, you could stay in Florence a number of nights to permit to visit the surrounding areas. Just devote at least 2 full days to Florence, however.

Padua is a small city that can easily visited while you are in Venice. It's only about 25-30 min by train.

From Venice’s S. Lucia station, you can take a direct 30m train to Padua / Padova for the day. Buy tickets for the Scrovegni Chapel before leaving home. To get from Venice to Vicenza takes 1h.
Why not sleep in Venice and Florence only? There are lots of good day trip options from Florence too. You can take a bus from Florence to Siena (1h 15m) and a direct train from Florence to Lucca (1h 30m). You can also take a direct train to Pisa (1h 15m), etc.

Tammy, I would spend three nights in Padua. With five each in Venice and Florence, there's your two weeks!

Look at Bassano del Grappa with its Alpine setting yet close to Venice. Not a big city.
The Lakes? We have been to the big three, and have been to Lake Como four times.Besitiful scenery.
Dolomites? Stunning scenery accessed from charming Ortisei!
Bologna is fabulous but your husband doesn’t like cities. It might change his mind!

The South Tyrol museum of archaeology, in Bolzano, has the remains of Ötzi the Iceman.

Verona - the city of Romeo and Juliet and Roman ruins and coliseum.
Bolzano/Trento/Merano and the Dolomites
Bergamo, Sirmione, Bologna, Modena etc
From Florence, rent a car and explore Tuscany

Personally, I would not stay 5 days in Venice. I have been to Venice three times - including a few months ago - and I found the place annoying now - completely overrun with tourists, horrible expensive restaurants with bad attitudes, stunningly expensive gondola rides. The only way I got a good meal was to leave Venice and take a short train to Treviso.

I'm a big fan of Padua, though it is not a tiny place. To me it has more to see than Vicenza--though the latter has half the population and definitely feels smaller, which may be a plus for you on this trip.

I know not everyone agrees, but I have a hard time paying inflated hotel rates in a super-popular city and taking multiple day trips to cheaper towns. Padua has enough sights to keep you busy for multiple days, and some of the Brenta villas are accessible by bus as well as by (slower, more expensive) boat.

Not as geographically convenient but worth considering is Ravenna. In terms of population it's between Padua and Vicenza in size. The mosaics are magnificent, the historic center is attractive and the city wasn't remotely inundated with tourists as of last September.

Even staying only five days in Venice, the weekly vaporetto pass for 65 euros might be very worthwhile. Single tickets are now 9.50, which I agree is exorbitant; it feels like a tourist tax.

Hi Tammy, which airport will you use to fly home? If Malpensa, maybe do something like Parma, Cremona, or Bergamo (stay in the Citta Alta). If Venice, then Verona, Ferrara (day trip to Ravenna for the mosaics), or even Mantova.

Lucca can be a day trip from Florence or many options. Any interest in attending a local festival? Those can make a smaller city into a wonderful destination.

In the north, consider Siena, Lucca, Pisa, Ravenna and Verona. However, you are missing Rome and can easily do it if you have two weeks in Italy.

Padua is a small city rather than a village and personally it doesn't give me the feeling of a quiet and relaxing place despite the amount of sights and monuments (personal opinion).
From Venice there are several options:
- Treviso, the small Venice, easily accessible by train from Venice (30 minutes).
- Vicenza, on the same railroad line of Padua and Verona.
- Bassano del Grappa, a small town near the alps and famous for Grappa liqueur, accessible by train but if you have a car it's better since the train station is a little bit far from the center.
- Asolo, a real "village" near the hilly region where prosecco is produced. The town extends around a fortress built on the top of a cliff
from which you can enjoy a nice view of the lands below, (acessible by car).

Thank you so much everyone. I am off to happily research some of these options! We are not sure of flights yet, but hope to fly into Venice or Milan.

Tammy, you have a lot of great suggestions for the area. I think you are wise to save Rome for another trip--it deserves at least 5 nights, preferably more. We had 8 nights and loved it, as part of a trip that included Naples, Pompeii, and the Amalfi Coast.