Florence/Tuscany Itinerary Advice?

I wouldn't split nights since you are staying only 5 nights in Tuscany, including Florence, and changing hotels is time consuming.

It's hard to give advice on whether to stay the entire time in Florence and do day trips out of town by bus/train/organized tour or if rent a car, stay out of town (or at least out of the Florence city center, which is closed to traffic) and visit Florence from that out of city center/ out of town location. That is really a decision that only you can make, depending on your interests and budget. Renting a car will cost you approximately $100/day these days, although accommodation costs maybe a bit less away from the city.

July is hot everywhere, and Florence, which is a furnace at the bottom of a narrow valley, is no exception, therefore wherever you decide to stay make sure it has AC. If you stay out of town, or out of the city center, I would also look for a place with a swimming pool (in the city center hotels with pools can be counted with the finger of one hand of a person who has lost some fingers).

If you prefer to stay out of Florence, based on the places you want to explore by car, it is probably best if you stay somewhere not too far from the freeway that connects Florence to Siena. That will give you quick access to Florence, Siena, San Gimignano, Chianti, Montalcino, and also Montepulciano, although Montepulciano is a bit farther south from Siena.

I agree that I would not recommend changing locations for 5 nights. And our making sure you have AC. Touring wineries in Italy is not like touring wineries in the US (I'm assuming you are US or North America based}. Look for a wine and our food and wine tour. I highly recommend ToursbyRoberto but if you are talking about this July he might be booked. parking in Florence could be an issue. We have come to us private driver a lot more then renting our own car mostly because of the parking issues.

Thank you so much for your insight Roberto and Donna! After thinking more about it, we have decided to take out renting a car. Especially because we are most excited about the wineries and probably not a good idea to drive after wine tastings.

I’m leaning towards staying in Florence all 5 nights with a couple day trips out to the countryside. The first couple days we would hit the major sights in Florence. Then our top day trips outside of the city are Chianti vineyards, Montalcino/Montepulciano vineyards and seeing Siena. I spoke with Roberto from ToursbyRoberto and he does have availability for a food & wine tour that includes Chianti and Montalcino, leaving from Florence. He said Montepulciano is easier to get to from Siena. I guess I thought Montalcino/Montepulciano were the same distance. But if we had to pick one I would love to do Brunello wine tastings in Montalcino.

Knowing the things we would like to do and see outside of the city, would it make more sense to do 3 nights in Florence, and 2 nights in Siena? Or should we just do 5 nights in Florence, day trip to Siena and one of the tours to Chianti/Montalcino. Not sure if this matters, but after our last night we are heading to Positano, so assuming we would have to be in Florence anyways on the last day to take the train from there to Naples.

Also, I spend a lot of time reading comments from these forums. As far as hotels, Roberto, it sounds like you highly recommend La Scaletta. I love the views from the terrace. If we stayed in Florence all those nights it would be nice to have a rooftop to come back to for a drink and take in the views. I wanted to ask, for a couple that has never been to Florence (and Italy in general), will we be fine staying across the river? For context, the things we want to do in Florence: Accademia, Uffizi, Climbing Duomo, Boboli Gardens. And just explore the city ourselves. I know there are pros and cons to staying across the river as opposed to near the Duomo. The other hotels that still have availability for this July are Hotel Duomo, Hotel Centrale, Hotel Silla, Relais and Maison Grand Tour, and Galileo hotel. Clearly I only use recs from RS haha. I’m torn between booking a hotel that’s near the major sights or across the river.

Montalcino and Montepulciano are equidistant from Florence, but they would be reached using different routes.

The route to Montalcino is via Siena through the Raccordo Autostradale (the freeway to Siena). The route to Montepulciano is via the A1 freeway via Arezzo/Bettolle. Either requires about 1.5 hours drive from Florence.

Both would be more easily reached from Siena, which is closer to both, but even from Siena we are talking about 1 hour drive, so not much closer. I would not waste time changing hotels (always time consuming considering packing/unpacking and check-out and check-in process) to save just half hour drive. You would spend that much time just to pack and check out of your hotel.

You can find Brunello tasting anywhere, not only in Montalcino. I've done Brunello tasting in Pienza, in Montalcino, in Montepulciano, or even in Florence. If you care more about wine than anything else you can go to the Enoteca Zanobini next to the San Lorenzo Central Market on Via Sant'Antonino and drink Brunello to your heart's content (I do every time I pass by it).

La Scaletta is a hotel where I have stayed and I recommend (I think Rick Steves also recommends it) but there are many others. The location is excellent since it's just 1 min walk from both Ponte Vecchio and Palazzo Pitti (Boboli Gardens). Piazza Signoria and the Uffizi are only 5 min walk away, the Duomo about 10 min walk, and the station less than 20 min walk. As long as you are inside the historical center (which includes the Oltrarno) you are never more than 20 min walk from everything. The Oltrarno is generally less crowded with tourists, however via de Guicciardini, the main street between Ponte Vecchio and Palazzo Pitti where La Scaletta is, has a lot of foot traffic, especially during peak tourist season (Apr-Oct).