6 Nights in Florence

With six nights spend three nights in Florence and buy tickets for the Uffizi Gallery before leaving home.
If you can find a driver to pick you up in Florence and drive you to Volterra that would be perfect. Spend one night in Volterra and the next day hire a driver to drop you off in Siena. Spend two nights in Siena and after your first night in Siena hire a driver to take you to Montepulciano through Val d’Orcia for the day: https://lovefromtuscany.com/scenic-drives-in-tuscany/.

Welcome back!

My vote is usually to stay put and do a couple day trips. Bologna is a half hour away by train, so is Pistoia. Siena is an easy bus ride and I would think it would be wonderfully uncrowded in February.

In February, I'd probably just do a wine tasting at an enoteca in Florence, or drink a different wine with every meal.

For Florence itself, there are so many things to see that it would help to have some idea of what you are interested in.

Will you be flying in and out of the Florence airport? It may be a bit more expensive than using Milan or Rome, but it's so convenient and doesn't waste your time. If you use Google Flights alerts, you should be able to find a really good deal because you are going in February.

Glad to hear that you are making this dream trip come true. Lots of options to consider. First of all, are you flying in and out of Florence or another city?
Possible daytrips from Florence if you stay all your nights there: maybe a daytour of the Tuscan countryside, wineries, medieval towns. My family did a full joinable Tuscan daytrip with Roberto Bechi a few years ago and enjoyed that. Look up Tours by Roberto. He is featured in several Rick Steves videos. Last year I did a daytrip to Siena and San Gimignano withTours in Tuscany. There are lots of tour companies in Florence with good reviews that offer all kinds of daytrips. San Gimignano was very pretty and nearby Volterra is also attractive. Lots of wineries in Tuscany. maybe an overnight stay in an agriturismo? Siena is lovely in my opinion, either by daytrip or overnight for two days. You can go there with a daytour group, or private driver or bus or train. Pisa or Lucca are easily done as a daytrip on your own by train and seem to be popular destinations. . Make sure you go to Piazzale Michelangelo across the river in Florence for great views of the city.

You can get ideas about destinations from this forum, guidebooks, Trip Advisor, YouTube videos, Instagram Tuscany accounts, etc. Search the forum for previous posts about Tuscany and possible daytrips from Florence. Enjoy your trip!

Updating to include that we plan to fly in and out of Florence. Thank you all for the tips so far!

Stay in Florence the whole 6 nights, and if you can fly to Florence even better, because if you fly out of Rome, you will have only 5 nights, as you would need to spend your last night in Rome since all flights back to North America depart in the morning and they require that you check in 3 hours prior to departure.

Just to see the very basic sights in Florence you need at least 3 nights in Florence. If you can manage to stay 3 more nights, you can take up to 3 day trips. There are at least a dozen prime destinations that you can reach within 1.5 hours of train or bus travel from Florence. I wouldn’t travel farther than that, since days in February are short (dark by 6pm).

We'll be staying 5 nights in Florence next April as part of a Taormina/Salerno/Florence/Rome 16 day tour by train. It will be our 3rd time in Firenze, but our cousins' first. I think the first key is to stay at a central hotel or AirBnB where you can basically fall out of bed and wander around, or take a break from touring and nip on up to the hotel for a catnap. We've stayed at a hotel in the central shopping district on via Tornabuoni, and then have stayed at an apartment across the street from the Florence SMN train station overlooking the Santa Maria Novella piazza itself. Both had their pros & cons, but I like near the station better. Less frantic it seemed, but that was February.

Very walkable, even across the Arno River to the Oltrarno area. But the main allure--at least for me--to staying put for all 6 nights as Roberto correctly recommends is developing a routine, shopping the market (Mercato Centrale) each morning, finding a vendor you like. Stopping each morning for a espresso & cornetto after a morning walk. Much easier to assimilate and get the Florentian vibe.

Our first trip, we did take one day and a guide picked us up along the river and drove us about 25 km south into Chianti, where we went to a winery where we met the vintner, toured the facility, sampled the SuperTuscans & had a private cooking class as well. It was a little expensive but wonderful. You must see the rolling hills of Tuscany.

We did visit Florence nine years ago, as part of a month in Italy.

We spent the entire six nights in Florence itself and then hired a driver for day trips and a transfer to Rome via some other sites.

We love wine and wanted to do lots of tasting, so driving ourselves wasn't a great idea, plus for us Australians it is the wrong side of the road.

We found this to be be a perfect way of seeing the city and lots of the stunning surrounding countryside.

I did do a blog about it so will add the link if you are interested in what we did.

http://v2.travelark.org/travel-blog-entry/djh1959/7/1431710456

Deb H thanks for the post about your great blog. I especially liked that you said what you ate at the restaurants.

Unless you want to rent a car for a few days to drive around Tuscany your best bet is to just stay in Florence as Roberto has suggested. Florence is the transportation hub for the region, so you'll be able to see many of the nearby hill towns independently using local trains and buses, or by signing up for organized day trips and tours according to your interests ... there are plenty to choose from.
6 nights/5 days really isn't much time - suggest simplifying your logistics by just staying put in Florence for the duration of your stay.