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Tuscany day trip suggestions sought

Hello! We are looking for day trip suggestions for Tuscany region. We will have four full days to explore, June 10-13, 2025. We are staying at a property just a few miles from San Gimignano .
Day trips being considered, not necessarily in this order:
San Gimignano (very near our lodging). We will probably spend ¾ day here, including lunch, and then return to our lodging to enjoy the pool and have dinner onsite.
Sienna. Should we allow a full day, including staying for dinner?
Looking for suggestions for our other 2 days.

Just a note: about 20 years ago, we visited Volterra. We were not planning on spending the full day there on that particular trip, but found it delightful and stayed all day. The Etruscan museum was great! We’re not opposed to visiting Volterra again as 3 of the 5 of us have not visited there before. Thoughts?

As for winetasting, only 2 of the 5 of us drink wine, so not a big priority to visit wineries, but would like to try to visit one or two incorporated in during our day trips. Any specific recommendations?

Thanks so much for any suggestions!
Amanda & Dave

Posted by
9021 posts

Volterra which is fairly near San Gimignano has a wonderful Etruscan museum and quite a few Roman ruins. You could combine it with your visit to SG.

Siena is worth a day -- and is ringed by parking lots (be sure you take clear note of where you park as it would be easy to forget which of the garages that circle the historic center you used. Note the streets you took and the gate you used to enter the old city.

Lucca and. Montepulciano are two favorites of ours. And there are several wonderful rural abbeys -- pick one on the way to wherever else you are going. The possibilities are endless.

Posted by
3403 posts

Not sure how fare Montepulciano is from where you’re staying but if you can drive through Val d’Orcia to get there you won’t be disappointed.

Posted by
331 posts

I will add another vote for Volterra and Lucca. And if you make the drive to Val d'orcia for Montepulciano, I would also suggest Pienza.

Posted by
331 posts

Forgot to mention Certaldo, which is in the general area of SG and Volterra.

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8 posts

If you’re visiting Tuscany and want a wine tour that goes beyond the usual, I can’t recommend this enough. Whether you’re a wine lover or enjoy good food, beautiful landscapes, and authentic experiences, this tour is a must.

You can find all the details and book your spot here: https://www.italyandwine.net/san-gimignano-wine-tour

The day started with a drive through the gorgeous Tuscan countryside. Rolling vineyards stretched as far as the eye could see, dotted with olive groves and charming stone farmhouses. Our guide, a true wine expert, made the journey even more interesting, sharing stories about the region’s history, wine traditions, and even a few local secrets.

Our first stop was a family-run winery specializing in Vernaccia di San Gimignano. Now, I’ll be honest—before this trip, I wasn’t the biggest fan of white wine. But tasting Vernaccia here, where it’s made, completely changed my mind. It was crisp, elegant, and full of character, with citrusy and mineral notes that made it perfect for a warm Tuscan afternoon.

We walked through the vineyards, learning how these grapes thrive in the unique sandy soils of San Gimignano. The winemaker took us into the cellar, where rows of oak barrels held aging wines, and explained the production process with the kind of passion that only a true artisan can have.

By midday, we arrived at the second winery, this one famous for its Super Tuscans—rich, bold red wines that have put Tuscany on the world stage. But before diving into the tastings, we were treated to a homemade Tuscan lunch on a beautiful terrace overlooking the vineyards.

The food? Divine. Fresh bruschetta with olive oil from the estate, handmade pasta with a rich wild boar sauce, local cheeses, and tiramisu to finish—it was a feast. Each course was paired with a different wine, and the combination of flavors was pure perfection.

Trust me, it’ll be one of the best days of your trip. 🍷