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The Ultimate Tuscany Wine Crawl: Chianti, Brunello, and Everything In Between

Thrillist is a digital lifestyle media brand focused on food, drink, and travel for millennial and Gen Z audiences.

The route

11 stops·5 wineries · 4 restaurants · 1 hotel · 1 shop

1. 01

   WineryToscana

   Antinori nel Chianti Classico

   Built into a Tuscan hillside, this architectural stunner is where Antinori crafts legendary Tignanello and Solaia wines.

2. 02

   Restaurant

   Badia a Passignano

   Dine in a medieval monastery on Antinori's elevated Tuscan fare paired with their own Chianti Classico.

3. 03

   WineryToscana

   Castello di Ama

   Gaiole in Chianti estate pairing critically acclaimed single-vineyard Chianti Classico Gran Selezione with contemporary art installations.

4. 04

   Restaurant

   Osteria Le Panzanelle

   Locals queue up for handmade pasta and grilled meats at this rustic Chianti trattoria that's been the real deal for decades.

5. 05

   WineryToscana

   Poggio Antico

   High-altitude vineyards outside Montalcino yield structured Brunello di Montalcino built to age gracefully.

6. 06

   WineryToscana

   Casanova di Neri

   Casanova di Neri's legendary Cerretalto Brunello commands reverence from collectors willing to hunt and pay for perfection.

7. 07

   Restaurant

   Il Leccio

   Honest Tuscan cooking in Sant'Angelo in Colle where bistecca alla Fiorentina and handmade pici justify the detour south of Montalcino.

8. 08

   Hotel

   Hotel Il Pellicano

   Perched on Monte Argentario's cliffs, this legendary hideaway is where Italian film royalty lounges poolside and remembers why they came for wine.

9. 09

   WineryToscana

   Sassicaia — Tenuta San Guido

   Bolgheri's revolutionary estate that literally invented Super Tuscan wines and still makes one of the planet's most coveted bottles.

10. 10

    Shop

    Enoteca Italiana

    Siena's historic Medici fortress harbors an extraordinary rotating selection of wines from every corner of Tuscany.

11. 11

    Restaurant

    Osteria dell'Orcia

    Slow-food Tuscan classics meet cypress-lined hill views at this farmhouse gem in Val d'Orcia.