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Tuscany Wine Trail: Chianti Classico & Brunello di Montalcino

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The route

11 stops·5 wineries · 3 restaurants · 2 hotels · 1 shop

1. 01

   WineryToscana

   Antinori nel Chianti Classico

   Taste Tignanello and Chianti Classico Riserva at this iconic estate's stunning hillside cellar, built by one of Italy's most legendary wine families.

2. 02

   WineryToscana

   Castello di Verrazzano

   Thirteenth-century Tuscan castle where explorer Giovanni da Verrazzano was born and elegant Chianti Classico still flows today.

3. 03

   Restaurant

   Buca dell'Orafo

   Tuck into massive bistecca alla Fiorentina and ribollita at this beloved Florentine trattoria steps from the Ponte Vecchio.

4. 04

   WineryToscana

   Ricasoli – Castello di Brolio

   Italy's oldest winery, where Baron Ricasoli literally invented Chianti in the 1800s at this stunning Gaiole fortress.

5. 05

   Hotel

   Relais Vignale

   Settle into this converted noble residence in hilltop Radda, where vineyard views meet a welcoming wine bar.

6. 06

   Restaurant

   Osteria Le Panzanelle

   Hand-rolled pici and seasonal truffles shine at this family-run Tuscan osteria with a thoughtfully curated local wine list.

7. 07

   WineryToscana

   Banfi – Castello Banfi

   Medieval castle vibes meet world-class Brunello di Montalcino at this Montalcino legend, complete with thorough cellar tours.

8. 08

   WineryToscana

   Biondi-Santi

   Brunello's birthplace offers a cellar full of 19th-century vintages that'll make any serious collector weak in the knees.

9. 09

   Shop

   Enoteca Franci

   Montalcino's premier wine shop stocks an exceptional range of Brunello, Rosso, and Super Tuscans on the main street.

10. 10

    Restaurant

    Il Leccio

    Il Leccio pairs refined Sienese dishes like wild boar pappardelle with an impressive Chianti-focused wine list in Villa a Sesta.

11. 11

    Hotel

    Borgo San Felice

    This restored medieval hamlet in Chianti Classico doubles as a luxe hotel with its own winery, perfect for sleeping where the grapes grow.