Top 6 Val d'Orcia Day Trips from Florence

1.Full Day Tour to Val d’Orcia and Gladiator’s Fields with Wines

★★★★★★★★★★4.5 · 1,106 reviews · 11 hours 30 minutes (approx.) · from $94Our pick

Ride from Florence through Val d’Orcia to Montalcino, Pienza and Montepulciano, with free time in each town and tastings of Brunello and Vino Nobile. A local guide leads the day, though the guide varies. Expect a long coach ride, hilltop streets, a cheese pairing and a brief look at the Gladiator filming area.

“Daniel was excellent guide. This trip is definitely for wine lovers. Two very special family run wineries. Amazing home cooked lunch and some free time in San Gimignano. Lots of wine so pace yourself”

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2.Val D’Orcia Tour with Wine Tasting

★★★★★★★★★★4.6 · 1,106 reviews · 11.5 hours · from $108

Travel from Florence by air-conditioned coach to Val d’Orcia’s hill towns. Visit wineries in Montalcino and Montepulciano for Brunello and Vino Nobile tastings, sample Pienza’s Pecorino, and enjoy free time in all three towns. An English, Portuguese, or Spanish-speaking guide leads the 11.5-hour day; lunch is not included.

“Our trip to Val D’Orcia was amazing. We had Julia who did an excellent job on a multilingual tour, and shared lots of different information (restaurants, key sights, etc) at each stop. For those looking to explore this area, you can beat this tour!”

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3.Val d’Orcia Brunello Wine Tour with Montalcino and Montepulciano

★★★★★★★★★★4.5 · 359 reviews · 10 hours 30 minutes (approx.) · from $277

Leave Florence in an air-conditioned van for a small-group day in Val d’Orcia. Visit a family winery near Montalcino, eat a three-course lunch in Pienza, then tour Montepulciano’s underground cellar and taste local wines with food pairings. The group is capped at eight; drivers such as Simona, Luca, and Mike have shared local stories along the way.

“Fantastic, what a fun excursion to the wine country in Tuscany. This was a small group who after the first wine tasting at a beautiful vineyard we all became friends. The guide was fun. We had a lot of laughs. We enjoyed quality wines, cheeses and the pairings perfect. The underground experience was unique. Highly, highly recommended this tour. Probably the best wine testing experience I’ve ever had and I’ve been to many.”

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4.Valdorcia Wine, Brunello Montalcino, Montepulciano

★★★★★★★★★★4.8 · 238 reviews · 10.5 hours · from $265Top rated

Spend 10.5 hours in Val d’Orcia, traveling from Florence by air-conditioned van with no more than eight people. Visit two wineries for guided tastings, explore Montepulciano’s underground cellar, and stop in Pienza for a three-course lunch. Drivers such as Simona, Paola, Mike, and Salvatore have shared local history along the way.

“The tour is a wonderful way to explore and experience three magnificent places in the Val d’Orcia in the Tuscan countryside. Our guide and driver was Simona and she was a great, safe and efficient driver through the highways and through the small towns, as well as being so well versed about the areas and towns and wines as well. Thank you Simona! The first small and beautiful family winery was very rewarding and they have very high quality Brunello wines and a very warm welcoming atmosphere!! Our second stop, the Medieval village of Pienza, words cannot describe the stunning views over the valley and the ancient walkways and stone…”

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5.Orcia Valley, Montalcino, Pienza with Lunch & Wine

★★★★★★★★★★4.7 · 225 reviews · 12 hours · from $123

Ride from Florence into the Orcia Valley for free time in Pienza and Montalcino, a visit to the Temple of Brunello, lunch with three local wine tastings, and a stop at Sant’Antimo Abbey. Your guide shares context along the way; guide assignments vary. The 12-hour day includes round-trip transport.

“Nice and small group and fabulous towns with amazing views. Had a wonderful time with friends”

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6.Monteriggioni & Val d’Orcia Optional Wine Tasting

★★★★★★★★★★4.6 · 180 reviews · 11 hours · from $51Best value

Ride from Florence to Monteriggioni, Montalcino, and Pienza, with free time in each and a Templar Museum visit when available. Add a Montalcino tasting of Brunello, Rosso, cold cuts, and cheeses, or choose the bus-only option. Guides have included Chiara, Vanessa, Anna, and Ilaria; your guide may vary.

“We loved our Medieval Experience! It was a very well-organized tour with enough time in each city. Our wine tasting in the Fortress in Montalcino was so much fun, and totally worth it. Our guide (whose name I cannot remember, but who was from Brazil but grew up in Florence and had the most calming way of speaking) was wonderful—very informative and helpful. It was a very organized tour and I’d highly recommend it as a way to get outside of Florence to experience the countryside!”

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