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Tuscany's Greatest Hits: Chianti Classico, Brunello & Beyond

Wine Spectator is the world's most influential wine magazine, with over 400,000 print subscribers.

The route

12 stops·6 wineries · 3 restaurants · 2 hotels · 1 shop

1. 01

   Hotel

   Check-in at Castello di Casole

   Sleep in a restored 10th-century castle where Belmond luxury meets Sienese vineyard vistas.

2. 02

   WineryToscana

   Antinori nel Chianti Classico

   Antinori's gravity-fed hillside headquarters crafts Tignanello and Solaia, two of Tuscany's most legendary Super Tuscan wines.

3. 03

   Restaurant

   Lunch at Osteria di Passignano

   Michelin-starred Tuscan cuisine meets 14th-century stone walls and Chianti Classico at this refined Antinori estate restaurant.

4. 04

   WineryToscana

   Castello di Ama

   Gaiole's Castello di Ama pairs world-class Gran Selezione Chianti with an exceptional contemporary art collection that rivals its wine credentials.

5. 05

   WineryToscana

   Barone Ricasoli - Castello di Brolio

   Where the Baron literally wrote the Chianti rulebook, now producing the classics from a gorgeous Gaiole fortress.

6. 06

   Shop

   Enoteca Italiana

   Explore Italy's regional wines from a curated selection housed inside Siena's historic Medici Fortress, then grab a bottle to take home.

7. 07

   Restaurant

   Dinner at Osteria Le Logge

   Siena's most charming dinner spot occupies a 19th-century pharmacy and nails every traditional Sienese dish alongside wines that actually belong there.

8. 08

   WineryToscana

   Biondi-Santi Tenuta Greppo

   Montalcino's pioneering estate where Brunello was born, now housing a library of collectible vintages stretching back to 1888.

9. 09

   WineryToscana

   Casanova di Neri

   Montalcino's Casanova di Neri crafts Brunello so exceptional their Cerretalto earned a perfect 100-point Wine Spectator score.

10. 10

    Restaurant

    Lunch at Trattoria il Pozzo

    Rustic trattoria in Sant'Angelo in Colle dishing out pici al ragù and roasted meats with affordable local wines.

11. 11

    WineryToscana

    Sassicaia - Tenuta San Guido

    Bolgheri's legendary estate that sparked the Super Tuscan movement with Sassicaia, a Cabernet powerhouse that earned its own DOC.

12. 12

    Hotel

    Check-in at Relais San Pietro in Polvano

    Settle into this olive-estate agriturismo near Cortona for valley views, a pool, and the kind of quiet that makes Tuscany worth the trip.