Category Val d’Orcia & Tuscan Hill Town Trips

Florence · VAL D'ORCIA & TUSCAN HILL TOWN TRIPS

Val d'Orcia & Tuscan Hill Town Trips from Florence Worth Your Time

Florence experiences, compared clearly

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

Full Day Tour to Val d'Orcia and Gladiator's Fields with Wines - Montalcino for Brunello: cobblestones, then cellar time

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 $94Editor's first choice

Florence day trip to Val d’Orcia with Brunello in Montalcino, Pienza on foot, Vino Nobile in Montepulciano, and Gladiator spots.

“Well planned tour of 3 beautiful villages in Tuscany (Montepulciano, Pienza and Montalcino). Itinerary goes through beautiful sceneries and shows the real rural Tuscany. Visits to two wineries have been very nice and informative and wine was excellent. Our guide Lorenza and driver Manjula have been great and very helpful all the time. Definitely recommend this tour.”

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From Florence: Val D’Orcia Tour with Wine Tasting

From Florence: Val D'Orcia Tour with Wine Tasting - Getting started in Florence: meeting point and coach comfort

Val d’Orcia Brunello Wine Tour with Montalcino and Montepulciano

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano - From Florence to Montalcino: winery tour, Brunello talk, and tastings

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

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

Brunello day trip from Florence with Montalcino winery, Pienza lunch, and Montepulciano underground tastings in a small group.

“Great day in Tuscany. I want to say thank you to Simona and the wineries for making our experience wonderful. Simona went above and beyond to help make it a great day. Thank you Simona. Ci rivediamo presto speriamo!”

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Florence: Valdorcia Wine, Brunello Montalcino, Montepulciano

Florence: Valdorcia Wine, Brunello Montalcino, Montepulciano - Getting Started in Florence, and How the Day Moves

4.Valdorcia Wine, Brunello Montalcino, Montepulciano

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

Small-group Val d’Orcia day trip from Florence with Brunello tastings, Pienza Pecorino lunch, and Montepulciano underground wine and olive oil.

“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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Florence: Orcia Valley, Montalcino, Pienza with Lunch & Wine

Florence: Orcia Valley, Montalcino, Pienza with Lunch & Wine - From Florence to Pienza: getting into the rhythm

Florence: Monteriggioni & Val d’Orcia Optional Wine Tasting

Florence: Monteriggioni & Val d'Orcia Optional Wine Tasting - Leaving Florence with comfort that actually matters

Siena, Cortona, Montepulciano & Val D’Orcia in a Small Group Tour

Siena, Cortona, Montepulciano & Val D'Orcia in a Small Group Tour - Porta Romana and the Tuscan Countryside Drive

7.Siena, Cortona, Montepulciano & Val D’Orcia in a Small Group Tour

★★★★★★★★★★5.0 · 107 reviews · 12 hours (approx.) · from $241Highest traveller score

Small-group Tuscany day trip from Florence with Cortona, Montepulciano farm tastings, Siena, and Val d'Orcia views, plus wine.

“Our tour was with Alessandro, hes very personable and friendly. He did a wonderful job getting us around, explaining each stop and guiding us through each area. With the each stop, the views got better! Thank you very much foe your hospitality Alessandro, we very much appreciated you.”

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Brunello and Nobile, Wine Lover Tour Montalcino and Montepulciano

Brunello and Nobile, Wine Lover Tour Montalcino and Montepulciano - Montalcino: walled-town vibes and the Brunello production zone

Medieval Tour in Monteriggioni and Val d’Orcia from Florence

Medieval Tour in Monteriggioni and Val d'Orcia from Florence - Monteriggioni’s walls and the feel of a 1200 AD fortress

Lands of Brunello wine Pienza and Montalcino with Gourmet Lunch

Lands of Brunello wine Pienza and Montalcino with Gourmet Lunch - Florence pickup, coach comfort, and how the timing really feels

Exclusive Brunello di Montalcino tour from Florence

Exclusive Brunello di Montalcino tour from Florence - First winery reset: taking the break you came for

11.Exclusive Brunello di Montalcino tour from Florence

★★★★★★★★★★5.0 · 45 reviews · 11 hours 30 minutes (approx.) · from $611

Private Brunello di Montalcino day trip from Florence with three winery stops, tastings, 3-course lunch, pickup, and a designated driver.

“It was one on the highlights of our vacation. My wife and I were picked up at our hotel in Florence and visited 3 vineyards. Great wines and delicious lunch served at Fanti vineyard. Unbelievable how beautiful the region is. A special thanks to our driver and tour guide Paola for making the day special.”

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From Florence: Siena, Cortona, Montepulciano & Val D’Orcia

From Florence: Siena, Cortona, Montepulciano & Val D'Orcia - Meeting at Porta Romana and settling into the mini-van rhythm

12.From Florence: Siena, Cortona, Montepulciano & Val D’Orcia

★★★★★★★★★★4.9 · 43 reviews · 10 - 12 hours · from $265

Private minivan day in Tuscany: Cortona, Montepulciano, Siena, and Val d'Orcia, with wine tastings and a Cinta Senese farm stop.

“The trip to Cortona, Montepulciano and Siena was fantastic. Our guide, Dom, was great at pointing out important places of interest. There were so much of the day to love - highlights were probably driving by the house for the movie Under the Tuscan Sun and the farm tour. Not only was it great to see a small local farm, it was the first and best opportunity of the day for our whole group to really chat and get to know one another. Overall, it was a lovely day in the Tuscan countryside!”

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VIP Brunello Montalcino, Montepulciano & Val d’Orcia with Lunch

VIP Brunello Montalcino, Montepulciano & Val d'Orcia with Lunch - Chianti hills and Monteriggioni: the scenic warm-up

13.VIP Brunello Montalcino, Montepulciano & Val d’Orcia with Lunch

★★★★★★★★★★5.0 · 40 reviews · 9 to 10 hours (approx.) · from $231

Small group Brunello day trip from Florence to Montalcino and Montepulciano with Val d'Orcia views, plus a winery lunch tasting.

“What a fun and relaxing day with Morad sightseeing in Tuscany and enjoying our lunch at a winery. Morad was very knowledgeable and made our day together one of the best ones of our trip. Highly recommend taking this tour.”

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Chianti Classico, Montalcino, Montepulciano by minivan: Wine Tastings & Lunch

Chianti Classico, Montalcino, Montepulciano by minivan: Wine Tastings & Lunch - Castellina in Chianti: cellar learning plus a classic tasting menu

14.Chianti Classico, Montalcino, Montepulciano by minivan: Wine Tastings & Lunch

★★★★★★★★★★4.5 · 32 reviews · 10 hours (approx.) · from $348

Florence to Chianti, Montalcino, and Montepulciano by minivan with tastings and lunch for a small-group day of wine country views.

“The landscape on the drive was surreal, everyone fell in love with Andrea at Mazzarrini. The wine selections were fantastic, and the Brunellos with pasta lunch put me in a coma on the drive back. 10/10 would recommend!”

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Val d’Orcia private tour: Montalcino, Pienza and Montepulciano

Val d'Orcia private tour: Montalcino, Pienza and Montepulciano - Cappella Madonna di Vitaleta: the short stop that hits hard

15.Val d’Orcia private tour: Montalcino, Pienza and Montepulciano

★★★★★★★★★★5.0 · 31 reviews · 10 hours (approx.) · from $654

Private Val d'Orcia day trip from Florence to Montalcino, Pienza, and Montepulciano with photo stops, free time, and wine lunch options.

“We were picked up by Clint at our hotel and traveled the beautiful countryside on our way to Montalcino where we enjoyed tasting of some of the best Brunello wines. Next stop was a beautiful small church with scenic countryside views. Then we stopped in Pienza, a quaint small city with plenty of places to have a nice lunch. Completed the day with a stop in Montepulciano for some more tastings of Nobile grapes. Overall an awesome experience 👏🍷😎”

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