50th birthday stop between Venice and Rome
 

My husband and I are Travelling by train from Venice to Rome in early November. I am celebrating my 50th birthday and need suggestions as to where to stop for 2 nights for my birthday, somewhere between these 2 cities, preferably somewhere easy access by train although we are not opposed to car rental. The previous week we are spending in Tuscany (Florence, Pienza, Montalcino, San Gimignano,). Would like suggestions for a nice restaurant for birthday dinner and an interesting place to explore.

Would you be interested in Bologna?

It's a nice stop for early November because the streets are covered, so if you get rain, you can still go out and about sightseeing (as long as you are dressed warmly). If you like pasta, Bologna is a LOT of fun.

Downside is that November hotel rates tend to be pricey, but you can get around that somewhat with a b&b stay, and many of them are VERY nice. For a special treat, I would suggest Antica Casa Zucchini, and to check out Bologna nel Cuore.

There are some very nice restaurants in Bologna depending on your taste and budget. The stars of the show in Bologna is pasta and pork, but there are also some restaurants who do other dishes -- fish, veg, turkey, truffles -- nicely.

Or -- if Bologna doesn't float your boat and you don't mind making a dogleg for art, then Ravenna is spectacular and great for lovers of seafood and non-touristy places. If you would prefer someplace smaller than Bologna, with a brief change of trains in Bologna, you can have either pretty Modena (food, Pavarotti and cars) or atmospheric Ferrara (history, bicycles and fog).

You cannot miss Florence

Bologna is a great suggestion because you'd probably have a fantastic meal there, one fit for a milestone birthday. I love Ravenna too but its a little out of the way. If you like mosaics - definitely investigate Ravenna.

Another option would be Verona - it is a gorgeous city with lots to see and do. I had a wonderful meal at Tre Marchetti there but that was three years ago.

We love Orvieto. Wonderful Duomo, magnificent views in every direction, some good restaurants.

Byrd

I loved Orvieto and from there would love to visit Civita di Bagnoregio for something unique.

Second and third the suggestions for Bologna and Orvieto - Orvieto could be a base to visit nearby Montepulciano, a classic hill town easily gotten to by train and bus via Chiusi. Bologna is much bigger and can easily occupy a few days - Bologna to me is one of the vastly overlooked cities in Italy just because it is dwarfed in folks minds by Venice, Florence and Rome. and in November's often foul weather many Bologna walkways in the city center, which is said to have more medieval buildings or such than any city in Italy, the walkways are covered with porticos. A large university right in the town center livens the city up and yes I can see and smell the chestnuts (maroni I think) roasting from street vendors booths at that time of year.

I just came back from an Italy trip where I've stayed both in Bologna and Orvieto. Bologna is indeed an underrated destination. I found it a much nicer place to stay than, for example, Florence, if only for its lack of tourist crowds.
As commented above, it would give better chances of finding an appropriate restaurant than small-town Orvieto.
Bologna is just two hours from Venice with the cheap regionale train and another two hours by the express Frecce train to Rome. (Advance booking for the express train to Rome on https://www.lefrecce.it gives you a considerable discount: EUR 24 instead of EUR 49, which can be invested in that anniversary diner.)

Another vote for Bologna!