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Tuscany Through a Glass: Chianti, Brunello, and the Art of the Slow Sip

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The route

12 stops·5 wineries · 3 restaurants · 1 cafe · 1 hotel · 1 activity · 1 shop

1. 01

   Hotel

   Check-in at Castello di Casole

   Sleep in a restored 10th-century castle overlooking 4,200 acres of Tuscan countryside at this Belmond estate.

2. 02

   WineryToscana

   Antinori nel Chianti Classico

   Antinori's jaw-dropping hillside winery showcases Tignanello and Chianti Classico Riserva through cellar tours and tastings.

3. 03

   Restaurant

   Lunch at Buca Mario

   Florence's venerable 1886 institution serves bistecca alla Fiorentina and ribollita in a setting as storied as its menu.

4. 04

   WineryToscana

   Castello di Ama

   Gaiole's Castello di Ama merges world-class Gran Selezione Chiantis with an stunning outdoor contemporary art collection by Kapoor and Bourgeois.

5. 05

   WineryToscana

   Dievole Wine Resort

   Medieval Tuscan estate crafting benchmark Chianti Classico, where vineyard strolls and tastings unfold across storied rolling hills.

6. 06

   Shop

   Enoteca Italiana

   Siena's fortress wine library spotlights smaller Tuscan producers in a setting that's as impressive as the bottles themselves.

7. 07

   Restaurant

   Dinner at Osteria Le Logge

   Refined Tuscan fare and stellar regional wines await in a 19th-century pharmacy that's become Siena's most cherished dining destination.

8. 08

   WineryToscana

   Banfi (Castello Banfi)

   Castello Banfi's medieval charm and pioneering spirit shaped modern Brunello, now showcased through castle tours and a wine museum.

9. 09

   WineryToscana

   Poggio di Sotto

   Tiny biodynamic producer in Castelnuovo dell'Abate crafting collector-worthy Brunello di Montalcino that rewards patience.

10. 10

    Cafe

    Coffee at Caffè Fiaschetteria Italiana

    Founded in 1888, this atmospheric Montalcino café serves the perfect espresso pit stop before tackling the town's medieval fortress.

11. 11

    Activity

    Walk the Walls of Montalcino

    Climb medieval ramparts for sweeping vistas of UNESCO-listed Val d'Orcia's iconic cypress-studded hills and sculpted landscape.

12. 12

    Restaurant

    Dinner at Trattoria Il Pozzo

    Wild boar pappardelle and pici cacio e pepe shine at this beloved Sant'Angelo trattoria, best washed down with local Brunello.