My business trips look a lot like leisure travel as I visit our producers (vendors). This post includes ideas in no particular order.
On some of my trips, I’m alone at night so I often like to be in town to walk to dinner.
A beautiful resort in the Chianti Classico: Dievole. Find the web site. It is fabulous and located between Siena and Florence.
Also outside Florence in Bagno a Ripoli is this very nice small resort and excellent restaurant.
http://www.ristoranteal588.com/it/
http://www.borgoivicelli.com/en/
As a family, we stayed in this apartment in Florence. It is a 5 minute walk to Santa Croce and one of the neighborhood markets is nearby, San Ambrogio. This is an easy walk to the Ufizzi and the Duomo.
https://www.vrbo.com/68776
No one has mentioned Lucca, an amazing small city between Florence and the sea on the western coast. They are famous for music concerts in the summer and the walls of the city are a ring for walking or bike riding.
Do you know about Panzano? It’s a small town in the Chianti Classico — and the big feature is the larger-than-life Dario Cecchini, the Dante-quoting butcher — with his collection of restaurants. Dario’s mission is that if one is going to butcher an animal, there should be no waste.
Oh, and Verona is just gorgeous — the old city, the river … The opera (amphitheater).
Near Montepulciano, in Montichiello, Daria has a couple of restaurants and apartments. Take a look.
https://www.ristorantedaria.it/en/ristorante-daria/
Of course, Bologna is fascinating, the restaurants are great, and there are fabulous food tours to Modena and Parma.
If you go to Rome, I’ve stayed in this apartment twice:
https://www.vrbo.com/en-ca/cottage-rental/p384199vb
In Livorno, I’ve stayed at this hotel. It’s old and classy. But the rooms are modern. It’s across the street from the sea.
https://www.ghpalazzo.it/en/hotel-livorno/
I’ve lost track. Did I mention Ancona? A smallish city on the Adriatic. It’s certainly the less touristed side of Italy. I took a train from Bologna and the ride along the coast was beautiful. I stayed outside the city at Azienda del Carmine, an agriturismo: https://www.aziendadelcarmine.it/
This year I’m hoping to get to Calabria, or maybe Sicily. I’ve been as far south as Campobasso, and to the north I’ve been from Milan to Trieste (fabulous, but beyond Venice).
We once used airline miles to fly into Zurich and then took the train to Milan and beyond. I can’t think of a better train trip.
Note: if you drive, many of these towns have ZTLs (restricted driving areas). Learn the signs and ideally have GPS that warns you with enough time to stay out of the zone.