Florence and one other city? Bologna? Siena?

If your wife loves Florence, just stay in Florence and visit other places from Florence on a day trip.
Bologna is 36 minutes away via high speed train. That’s shorter than a lot of people’s daily commute. Siena is even closer than Bologna, but, since there is no high speed train, the bus ride is 75 min. Siena can easily be visited in a day. You also have a bunch of other beautiful cities within 1 hour from Florence: Pistoia, Arezzo, Lucca, Pisa, to name a few. You can also hire a private driver to take you on a four hour tour of the Chianti countryside or other small towns in the area, like San Gimignano and others. Florence is a perfect hub for Tuscany, and, thanks to high speed trains, Emilia Romagna as well. You can even take a day trip to Venice or Rome. Both deserve more than a day, but if you want, they are within 2 hours from Florence.

What Roberto da Firenze said.

Listen to Roberto!

Especially listen to the first line of my reply.
Because you are in your early 30s and probably not married for too long, but I, at my age and after almost 30 years of marriage I can assure you that a happy wife makes a happy life, whereas a sad spouse puts you in the dog house.

Thanks so much, Roberto and others!

My wife has expressed she'd like to sleep in one more city than Florence. Since we enter Italy via Rome (a city I love but don't plan to visit this time) I'm considering perhaps one stop inbetween before we finish the 4-5 days in and around Florence. With that, I was considering some of Rick's 'Heart of Tuscany' recommendations, such as Montepulciano.

We'd spend a couple nights there, make our way to Florence to enjoy the city, add one or two day trips to Lucca and/or Bologna sprinkled in before flying home.

Thoughts? Other suggestions?

Orvieto is a nice stop for a night or two.

Agriturismo Marciano just outside of Siena is a great place to sleep. The owners often serve multi-course evening dinners for guests at a communal table, pairing each course with one of the organic wines they produce. Hands down, the best food I had during my 3-week trip through Italy in 2015. I'm not sure how COVID is impacting this. https://www.agriturismomarciano.it

nik, welcome to the forum. It's hard to parse your question, especially with the statement that two 30-year olds are taking a six month trip around the world during Covid and finishing (?) in Italy. Are you in fact flying home after these 7 days in Italy? How many times have you been to Florence? How is it that you didn't hit Siena on those past trips?

Maybe English is not your first language, but it's also puzzling that you use the word "trip" twice to refer to one week of a six-month journey. It would help if you added your home city to your visible Profile for this newsboard.

It seems obvious that Venice is a "finish BIG" destination, one with lots of air options and no tedious drive back to Rome. Does finish BIG mean a super-luxury hotel, or is this a budget trip? It's also fair to consider Siena a big finish for someone who has been to Florence multiple times but never to Siena. They are the ultimate in contrasting Renaissance centers.

You wrote: The culture, the food, the people. We enjoy art, history, and architecture, but that is not the main driver for us. There are a lot of smaller cities in E-R where you might not hear English spoken during your one-night visit. But it sounds like you want a destination-restaurant for your last meal on the trip. And you'd want to be in a town on its market-day.

If you plan any time outside cities (you mentioned Montepulciano/Val D’Orcia area) you should rent a car either when you leave Florence (90 min drive to Montepulciano) or in nearby Chiusi (some rental car companies are walking distance from the Chiusi-Chianciano train station, located in the town of Chiusi Scalo (Scalo means station). A car is recommended to visit those rural areas where public transportation options are scant.

My wife and I spent 2 weeks in Florence in (I think) 2019 or maybe it was 2020. During that time, we took day trips to Siena and Pisa. I absolutely loved Siena. In particular, the cathedral. That cathedral is definitely on my top-10 list of things I have ever seen. The contents of that cathedral- the art, the walls, the floor, the architecture- were overwhelming. So I highly recommend Siena, just for that cathedral, although the rest of Siena is pretty amazing, too.

Siena is great, Bologna didn't blow me away.

Since you haven't been to Siena I would go there for 2-4 days. While it can be visited as a day trip from Florence, it is different to spend a few days (and evenings/nights) there. My first time there was on a day trip (via bus) from Florence but on a subsequent trip I stayed for three nights and loved it even more. If your wife wants another place to stay to combine with Florence it would be perfect.

I found Bologna quite to my liking and it is a good base if you want to visit several towns, because it's a rail hub. You can day trip to Ferrara, Modena, Parma, Padua, even wonderful Ravenna (though it's a longer ride).

The problem with Siena is the transportation. Trenitalia shows travel time of at least 3 hours (and up to 4.5) and at least one train change from Termini to Siena.

Orvieto is worth considering. Easy to fill 2 full days there, and good restaurants, lovely views . The underground tour is really interesting. Fast trains from Termini and to Florence.