My husband and I will be spending 5 nights in Tuscancy in early March, sleeping in Montecatini Terme and taking day trips from there. We have both been to Florence so we've decided not to spend any time there on this trip, instead focusing on several of the small towns in the area. We definitely have Lucca, Siena and San Gimignano on the list, but are also interested in touring a few of the wineries in the Chianti region. Looking for recommmendations on which ones and whether to do it on our own or hire a guide. We will have a rental car.
If you are serious tasters, hire a guide!
Because it's over that way, I'll mention that Antinori was a disappointment. The James Bond architecture is impressive, but the visit experience was poor. Poggio Antico was much nicer. Our favorite, Aviognesi is not near your visit.
Note that the better wineries require bookings. We chose to have our big meal of the day at wineries with ambitious lunch restaurants, rather than dinners. Our hotel was helpful in advance bookings. You do not need a tour or a guide.
I have some that, 5 nights in Montecatini Terme. We did day trips almost every day.
Rent a car and be sure your hotel has parking.
Montecatini Alto for dinner, cute little town above your home base.
Vinci, cool little Italian town with Leonardo museum, he was born near here.
Panzano, see the Dario the butcher for an interesting time
Go north of Lucca to the Devil's bridge, pretty drive up the river
Volterra for Etruscan and Roman history
Montepulciano for wine, or, www.decanter.com/wine-travel/italy/top-10-tuscan-wineries-to-visit-13770/
for many different chianti's, Antinori is good, we visited a winery near San Gimi that have vernaccia, we liked it.
And there is always Pisa, go see the Campo Santo while there, the burial ground by the duomo that was destroyed in WWII, in the book Saving Italy.
There is no shortage of things to do.