1st Time in Italy - Tuscany Recommendations

With only six nights and without a car, I think I would just stay put in Florence as a base of operations. You can do day trips via bus or train to Siena and Lucca and smaller towns in the Tuscan countryside, and you don't need to plan these in advance, so you can do as few or as many day trips as you want.

Alternatively, you could spend a few nights in Siena, which is a wonderful place to be in the evenings. If you decide to do this, I would head to Siena immediately on arrival and spend your first two or three of nights there, and the remainder of your time in Florence. One reason for doing it this way is that Siena is more of a medieval city and Florence is a Renaissance city, so it makes good historical sense to see them in that order. Also, from a purely logistical standpoint, you have a morning flight out of Florence, so you should end up there. If you do stay in Siena, Montepulciano is a closer visit from there than from Florence.

If it's within your budget to rent a car for just one day, I'd advise it. As you say, your time is short, and you'll waste a fair amount traveling by bus. With a car for a one-day rental in Siena, you could visit a handful of charming small hilltop villages and stop at a dairy farm to sample some cheese or at a vineyard to sample some wine.

Wine tastings are possible in town, but if you want to visit an actual vineyard and winery, you might want to book a tour, especially if you don't decide to do a car.

I'm concerned that if I don't land until around 6:30pm it'll be too late to get to Siena that night. Thoughts?

Buses from Florence to Siena run in the evening. Whether you would want to ride a bus in the evening after a long flight, only you can decide.

Your original plan is doable by public transportation, I have done it many times. What month you travel in might affect transportation schedules, so look into that before you commit.

I'll be traveling in November. it appears the last bus leaves around 2115 (having a hard time finding a current schedule). I would love to make it to Siena on day 1 but I think it will depend on how quickly I can get through the airport and into Florence.

Any other suggestions?

It will be dark by the time you get to Florence. Stay there for your first night and relax, you are in Italy, mission accomplished! Florence has plenty of amazing wine and espresso on every corner. Take off for Siena in the daylight when you are rested, you will even see some rolling hills.

My friend and I have a similar itinerary but we are staying longer and want to spend two nights around Montepulciano. Your recommendations in the 2016 Rick Steves book are booked. Do you recommend any others? We are interested in a farm environment with farm food and 4 star setting. Preferably two beds or rooms. So excited... will be in that area 04/10/16-06/10/16. Thanks so much!

Make sure to stay at least 3 nights in Florence. Have you booked accommodation? Are you alone (hotel and B&B) or a family (in that case an apartment is more comfortable).

Bus from Florence Bus station ( downstairs SMN) to Siena

Travel time

Notes
5:28
7:31
2 h 03 min
Change train in Empoli

6:25
7:55
1 h 30 min

6:46
8:39
1 h 53 min
Change train in Empoli

8:33
10:05
1 h 32 min

9:15
10:53
1 h 38 min

10:33
12:13
1 h 40 min

11:15
13:03
1 h 48 min

12:25
14:20
1 h 55 min
Change train in Empoli

13:23
15:05
1 h 42 min

14:09
15:35
1 h 26 min

15:17
17:05
1 h 48 min

16:00
17:34
1 h 34 min
Change train in Empoli

17:09
18:34
1 h 25 min

17:23
19:09
1 h 46 min

18:15
19:55
1 h 40 min

19:13
21:11
1 h 58 min

19:25
21:11
1 h 46 min
Change train in Empoli

20:30
22:08
1 h 38 min

23:07 00:50