After a perfect five days spent soaking up the last of the Italian summer sun at Le Sirenuse in Positano, we hopped in our convertible and drove north through the Italian countryside to Tuscany. As we sped down cypress-lined roads, we watched in awe as the temperatures dropped and the leaves slowly changed from green to gold. There’s something about the Tuscan color palette, the waning light, the abundance of the harvest season, and the warmth of the Italian people that makes Tuscany a truly dream destination in autumn. Scroll down to see our road trip and the best places to eat, stay, and explore in Toscana!
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- Borgo Santo Pietro: The epitome of relaxed Tuscan elegance, every inch of this intimate countryside retreat is tasteful and elegant. Set in a 13th-century villa, Borgo Santo Pietro is home to a gourmet cooking school and a Michelin-starred restaurant, plus a casual trattoria with an outdoor wood-fired pizza oven. We have been fortunate enough to stay at Borgo Santo Pietro several times and each visit it just keeps getting better.
- Villa Cicolina: If your Tuscan dreams consist of exploring the famed Val d’Orcia region from sunrise to sunset, Villa Cicolina is a beautiful option outside of Montepulciano. While the amenities are basic, the villa and gardens are absolutely lovely and the location simply cannot be beat.
- Villages: The medieval hill towns of Tuscany are truly exceptional and must not be missed. Our favorites are Montepulciano, Montalcino, Monticchiello, Pienza, and San Quirico.
- Abbey of Sant’Antimo: Go when the monks are chanting for an incredibly memorable experience.
- San Biagio: One of the most iconic sites in Tuscany, San Biagio is my favorite place to watch the sunset. On warm summer evenings, bring a bottle of wine and picnic.
- La Foce: The gardens are La Foce are truly iconic. Be sure to check the hours as it is also one of the best wedding venues in Italy and can sometimes be closed for private events.
- La Grotta: Outside of Montepulciano by San Biagio cathedral, this restaurant is utterly romantic.
- Caffè Poliziano: An iconic historic café in Montepulciano, stop in here for an espresso and be sure to peek out back to admire the absolutely breathtaking views.
- Alle Logge di Piazza: In the wine-centric Montalcino, this cozy café features incredible casual cuisine in a charming historic loggia.
Tuscany Wedding Photography by Molly Carr Photography