Tuscany 6 nights
 

This is a last-minute trip to Tuscany. We haven't even decided which city to fly into yet. Which is the best airport to fly into to spend one night maybe two nights and then drive into a city in Tuscany to use as a homebase. There are three adults. One of which has been in Tuscany several times. Interest our wine, food, and maybe a cooking class

Forgot to add. February 25 through March 6

It depends on the flight options from your home and where you intend to base in Tuscany. To which airports can you fly non-stop? How many connections would you have to make to arrive at Florence, Bologna, Pisa, etc. Milan and Rome "work" for Tuscany if you can fly non-stop.

So, where is your base?

Has the one traveler in the group driven in Italy? If not, you need to do some research on ZTLs (zona traffico limitato) which have been established in almost every town of any size in Italy. You can't just "drive into a city" unless you have permission to violate the boundaries of the town's zone in order to reach your lodging. When sightseeing, you park outside the ZTL and walk into and out of the towns. Whoever will be driving needs to get an International Driver's Permit.

We just go 5 nights into Florence in May. Just Florence.
In your case I would base there too and day trip to Siena San gimignano or Pisa. 2 day trips.

Tuscany is BIG! I think you first have to decide if you want northern Tuscany or Southern Tuscany--Val d'orcia. Each area is different and worth seeing in their own rights. Having been to Florence on a different trip, we spent 6 days in Southern Tuscany in September, based in Pienza and loved it. We used Montalcino Wine Tours (montalcinowinetours.com) for a winery tour and had an AMAZING time. At lunch that day we met other couples who were doing a multi-day tour with the same company--cooking one day, wine tasting another day and perhaps something on the third day. The owner's name of the tour company is Giovanni Paris.