We are staying nights in Tuscany, just outside of San Gimignano. Our tentative plans include 1 day in Florence, 1/2 day the Mall Firenze (looking for ideas what to do after that)?, 1/2 day at Antinori Chianti winery (looking for ideas after that), day driving south to Pitigliano.
Big question, should we spend our last day doing Siena & Montalcino. We are very interested in possibly a 1/2 day tour from Sienna which would include wine, cheese tasting, or is it something we could set up on our own? And, if so, ideas please for a winery in Montalcino for Brunello tastings?
thanks

Just recently returned from 2 weeks in the same area. We stayed in Colle di Val d'Elsa, about 15min from San Gimi. "We" included 3 generations ranging from 18yr old guys to their mid 70's grandma.
When you say "We" who does that include?

I would definitely recommend a day in Siena. Beautiful city, easy to get to/from. Just avoid Wednesdays which are big market day.

Other day trips included.

- 1 day at the beach, @ Cecina
- several 1day trips to Siena. Downloading the SiPark mobile app was very helpful to find parking. We used the Santa Caterina lot and it was easy in/out from the highway.
- go-karts, near Siena
- many short or long walking/biking excursions. The Via Francigena (pilgrims path) runs through San Gimi. If walking some of that trail interests you look up their website or download the app.
- Florence. Once by car (a hassle getting into the city and parking) and once by bus. You could also take a train from Poggibonsi, although bus is faster. For bus schedules, look at Tieme.it website.

If you want a "Tuscan/Chianti experience" I do NOT recommend Antinori. It is a mega scale commercial tourist operation - easy to get to from the highway, but massive scale. They have wines from all over Tuscany, and they'll be happy to let you spend $50 or $100 a bottle, if you want to. We were happy with $4-5 Chianti classico wines from the local supermarket. We did a short wine tasting at Antinori that was at best an ok experience, but not what we expected, and definitely not intimate or personal. Wines were excellent. Let me dig up some recommendations from our landlord & come back on post them here in the next day or so. I think one of them was Cesani, right near San Gimi. We did an in-town wine tasting right near our apartment that was fun.

Pitigliano is quite a distance from San Gimi - around 3hrs drive. Is there a reason you want to go there? You'll drive by dozens of other hill towns a lot closer to your base including Volterra, Monteriggioni and many others.

Happy to offer other tips/suggestions on the area so fire away.

Here are links to 2 posts of mine on rental cars and us immigration
Italy car rental options - what would you do?
US Immigration using "Mobile Passport" app

Thanks so much for your helpful reply. There are 3 couples and we are renting a 9 passenger van. The reason we are going to Pitigliano is because of the Jewish history of this city. I know it is a far drive, so we are looking for ideas as where to stop on the way back. It's our 1 "long" day we are having. I know Antinori is $$, but our friends are insisting on going there. I do like your other ideas and will get together tonite and see if we can incorporate some of these. Thanks again. Candy

Sounds great!

Our issue with Antinori wasn't the price, but rather the mega scale concrete /glass & commercialism. All of the wineries will let you spend $$$. I've done winery tours / tasting in Tuscany in the past where you've been in a room next to their vats and presses, and can feel & smell the earth as you taste the wine made right there. At Antinori you feel and smell the concrete, glass, and air conditioning and taste wines made up to 100's of miles away.

You will need to pre-book /reserve a spot if you want to do anything more than a walk-in tasting at the bar. They have limited spots and do fill up. Since your friends insist on going there, that's fine. Caveat emptor.

For dining nearby Antinori we were told this small town was worth stopping "Badia a Passignano" - a few small places, all of them good.

Depending on how early you leave Pitigliano, you could stop at either Abbazia di Sant'Antimo or Abbazia di Monte Oliveto Maggiore. There isn't much to see at Sant'Antimo, so it wouldn't be a long stop. In contrast, Monte Oliveto Maggiore has much to see and beautiful grounds to walk through (wonderfully shaded if it's a hot summer day). But unless you leave Pitigliano immediately after lunch, I'm not sure you'd arrive in time for a meaningful visit.


http://www.antimo.it/en/abbey.html

https://www.monteolivetomaggiore.it/

If you were thinking of a town to visit after Pitigliano, Montalcino is halfway between Pitigliano and SanG. You can do wine-tasting, including Brunellos, right in the town. No need to seek out a specific winery.

I would want a full day to see Siena.

The drive to the Mall Firenze will take you 90 minutes each way, and it doesn't open until 9:30 (June/July/Aug.) or 10:00 (rest of the year). I'm not sure if it works as a half-day excursion, but you could drive through Chianti on the way back. You could also drive through Chianti after Antinori or visit Monteriggioni, Volterra or Certaldo.

Thanks so much for your quick reply. I really appreciate it!

Thanks so much for you quick reply. I really appreciate it!

A note about Siena. Entrance to both the Duomo and up the bell tower both require timed entry tickets. I don't know if you can buy these online ahead of time but it's worth looking into. Of the 2, I'd say going inside the Duomo is the most amazing. No other place like it, and right up there with the most amazing churches anywhere. The view from the bell tower (400 steps up) is also amazing, and worth the 10 euro or so charge.

Re 9 passenger van and parking in Siena. Scratch my reco of Santa Caterina parking lot, as it's a tight, underground /multi level lot with height/size restrictions and tight turning radii. Definitely avoid the Stadio lot as well. Look at the SiPark app, or Parcheggio Siena online to see if they have anything about size restrictions. Parking near the train station may be your easiest bet, even if there is a walk (for the driver & navigator, at least). Fortezza is probably ok too, and easy to get to from the highway you'll be taking.

Or look in to taking a bus from Poggibonsi or San Gimi.., but with 6 of you the van is probably easiest. If you're looking for supermarkets, there are 2 mega stores in Poggibonsi. A Coop near the highway exit, and a Pam, on the side of town closest to San Gimi. The selection at these 2 stores rivals the biggest US supermarkets - so one stop shopping including lots of products for specialty dietary needs.