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For a tasting in Maremma, I would first look at Rocca di Frassinello, Fattoria Le Pupille and Tua Rita : they offer three quite different experiences. At Rocca di Frassinello, near Gavorrano, the visit combines the cellar designed by Renzo Piano, a space dedicated to the Etruscans and a tasting of five wines with charcuterie and cheeses; allow about 60 € per person and book in advance. It's a good choice if you also want to see the place, not just taste.
To discover the Morellino di Scansano, choose Fattoria Le Pupille, near Grosseto: several options allow you to compare Morellino, Riserva and more ambitious cuvées. The tastings are customizable, but the prices are not clearly displayed online; it's better to ask for the price and time slot before leaving. At Tua Rita, in Suvereto, the introductory package includes a visit and a guided tasting of five wines with local products: 90 minutes, €50 per person. It's in the Alta Maremma, so less convenient if you are staying in the south of the region.
Book in any case, especially on weekends and in summer: schedules and availability may vary. If you are near Castiglione della Pescaia, Le Mortelle is also an option to check; the cellar is a few kilometers from the town and offers tasting tours, but you need to check the time slots directly with the estate.
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