Hi all! I'm planning my first trip to Italy in early April with a friend. We're doing a few days in Rome and Florence before renting a car and driving down through Tuscany from Florence to Rome (flying in and out of Rome). I'm super excited and also super combating FOMO, and at this point I'm trying to trim down the itinerary so we don't overextend ourselves. That's not la dolce vita! I wanted to get feedback and opinions from those who have visited Tuscany, especially on what hill towns and Tuscan villages are must-sees and which ones can be missed.
On our first day we're planning on driving from Florence to Siena with a couple of pit stops at wineries on the way, making another pit stop at San Gimignano and ending the day in Volterra (our Airbnb is nearby). I opted to skip Monteriggioni in favor of San Gimignano - is that the right move? Am I trying to pack in too much here? I suspect that I am, but... FOMO.
On the second day we'll drive down to Montalcino, Pienza, Montepulciano, and the thermal baths at Bagno Vignoni before settling into our Airbnb nearby for the night. Of those three towns, how would you rank them from must-see to can-skip? Are there other villages in the area that we should consider instead? What wineries thereabouts are worth visiting? It's only about 3 hours of driving between all points (according to Google maps) as there's not a lot of ground to cover.
We don't plan on visiting any of the museums or anything at the towns, just walking around and sort of getting a feel for the places. I'm aware it's a bit of a whirlwind tour through Tuscany and we won't get a deep dive into any of the places we visit, which is fine by me for this trip. Still, any advice or a hard dose of reality from more seasoned travelers would be greatly appreciated!