Tuscany

If you’re dreaming of a road trip through Tuscany, this is everything we loved, bookmarked, and would do all over again.

Road Trip Route:

• Cortona

• San Gimignano

• Certaldo

• Siena

• Val D’Orcia

• Arezzo

• Florence (for all Florence recommendations, please click here!)

Where to Eat:

Cortona:

• La Bucaccia - Da Romano

• La Dispensa del Preludio

• Pizza e focacce

• Ristorante La Loggetta Cortona

  • Has a view overlooking Cortona’s main square!

• Ristorante Locanda al Pozzo Antico

San Gimignano:

• Ristorante Fuoriluogo

Certaldo:

• Ristorante Il Castello

  • Panoramic views - even if you can’t eat here, grab a spritz!

Siena:

• Golosi di Gelato

• Pizzeria Alle Scalette

Val D’Orcia:

• Podere Spedalone

  • Homemade pasta!

Arezzo:

• Vasari Cafe'

  • Casual Bar that has great views of the Piazza

Recommended Wineries:

*Reservations Recommended

• Fattoria Casa Sola 🏆

• Poggio Amorelli Chianti Classico 🏆

  • Book their wine tour & lunch - you won’t regret it! This was my favorite experience in Tuscany.

Things to Do:

Cortona:

• Walk through Le Viine Park

• Piazza della Repubblica

• Piazza Garibaldi

• Villa Bramasole

  • Also known as the Under the Tuscan Sun House

San Gimignano:

• Piazza della Cisterna

• PUNTO PANORAMICO

Certaldo:

• Funicolare di Certaldo

• Wander through the historic old town of Certaldo Alto

Siena:

• Duomo di Siena

• Piazza del Campo

Val D’Orcia:

• Cipressi di San Quirico d'Orcia

  • Viewpoint and Photo Spot with Cypress Trees

Arezzo:

• Duomo di San Donato

• Piazza Grande