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Villa della Regina

I think bringing a picnic is a great idea. The gardens are beautiful, and it's nice to enjoy some food there while taking in the views.
Make sure to check for any special wine tasting events before you go. I stumbled upon one, and it added so much to my visit!

If you can, try to squeeze in a short visit to the wine shop. They have some unique selections, and I found a lovely bottle to take home that wasn’t available elsewhere.
Poggio Rubino
Poggio Amorelli
Il Poggio Farm

I recomment bringing a picnic and enjoying the gorgeous views. The grounds are stunning, and they don’t mind you noshing while sipping their wine.
Antinori in the Chianti Classico
I heard the wine tasting is great, but try to book it in advance to avoid missing out. I went without a reservation and had to wait longer than I expected, which was a bit of a bummer.
Cantina Sant'Andrea Winery Di Gabriele Pandolfo

My advice is to buy a bottle or two to take home. Prices are pretty reasonable compared to what you’d find elsewhere, and they taste sooo much better fresh
Ca 'Dei Frati Farm
Azienda Agricola Ca 'Dei Frati
Tenuta Torciano
Fattoria Al Dotto Lucca

If you wanna save some cash, buy a bottle to take home instead of the tasting package. I spent less this way and had a nice souvenir.

I suggest arriving around 3 PM. I found that's when the sun sets beautifully over the vineyard. Perfect for some Insta-worthy photos!