Category 1-Day Tours

Small-Group Montepulciano and Pienza Day Trip from Siena

Small-Group Montepulciano and Pienza Day Trip from Siena - A Val d’Orcia farm lunch and Pecorino tasting: why this stop hits

1.Small-Group Montepulciano and Pienza Day Trip from Siena

★★★★★★★★★★5.0 · 281 reviews · 8 hours (approx.) · from $217Our pick

Small-group day trip from Siena to Pienza and Montepulciano through Val d’Orcia, with farm pecorino lunch and Vino Nobile tasting.

“Don't hesitate to book this outing! Our guide Keko was fantastic! He is extremely knowledgeable about everything the area has to offer from history to ecology. He is really kind as well and it was a pleasure to spend time with him. It was a fantastic day filled with the beauty of the landscape, a delicious homemade lunch at the Della Cinta Senese Pig Farm, wine tasting, and touring around two beautiful towns. A day we will never forget! Thank you for this special experience!”

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Small-Group San Gimignano and Volterra Day Trip from Siena

Small-Group San Gimignano and Volterra Day Trip from Siena - San Gimignano and Via Francigena: towers, alleys, and saffron

2.Small-Group San Gimignano and Volterra Day Trip from Siena

★★★★★★★★★★5.0 · 180 reviews · 8 hours (approx.) · from $217

Small-group day trip from Siena to San Gimignano and Volterra: Via Francigena walk, saffron lunch, and an alabaster workshop.

“The guide (Juliana) was excellent. Very knowledgeable about the area and the wine production. The visit to the winery was such a pleasure. I will definitely book a tour again through Viator !!”

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San Gimignano, Chianti, and Montalcino Day Trip from Siena

San Gimignano, Chianti, and Montalcino Day Trip from Siena - San Gimignano towers, piazzas, and the free-time reality

3.San Gimignano, Chianti, and Montalcino Day Trip from Siena

★★★★★★★★★★4.5 · 150 reviews · 11 hours (approx.) · from $168

Siena to San Gimignano, Chianti and Montalcino with wine tastings, Val d’Orcia views, and fortress-town time—no self-driving stress.

“Lovely day and easy itinerary - starts early but it's for the best - starting in san Gimignano before crowds arrive, then moving on to a great winery - lunch is an option there, unless you're bringing food or buy something to go in san Gimignano, this is really the only lunch option so I recommend it. The tour itself is a nice mixture of walking and wine interspersed so you never feel overly tired. Vincenzo was an excellent guide and really added a lot of history to what we saw. Great day overall highly recommend”

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From Siena: San Gimignano, Chianti, and Montalcino Day Trip

From Siena: San Gimignano, Chianti, and Montalcino Day Trip - Getting Started in Siena: Meeting Point, Group Size, and Comfort

5.From Siena: San Gimignano, Chianti, and Montalcino Day Trip

★★★★★★★★★★4.5 · 6 reviews · from $158Best value

Day trip from Siena to San Gimignano, Chianti, Val d’Orcia, and Montalcino. Tastings for Chianti and Brunello.

“Winery tour and information sessions were great. Free time in San Gimignano and Montalcino was amazing, more time in both would’ve been nice. The wines were good, especially in Montalcino, and the bruschetta and cheeses were a nice touch. The meeting point was not great. We were given a spot to meet at the train station but the van picked up in a different area. If I would’nt have called the tour operator they would’ve left us behind. They left another person behind who had to find their own way to San Gimignano to meet up with the group for the rest of the tour. The tour description said we’d…”

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Small-Group Arezzo and Cortona Day Trip from Siena

Small-Group Arezzo and Cortona Day Trip from Siena - Lucignano and the medieval lane-walk vibe

6.Small-Group Arezzo and Cortona Day Trip from Siena

★★★★★★★★★★5.0 · 4 reviews · 8 hours (approx.) · from $212

Small-group day trip from Siena to hill towns in Tuscany, with winery lunch and Chianti tastings, plus Arezzo and Cortona.

“It was a wonderful day in the Chianti region. Both Castellina and Greve in Chianti are beautiful towns not to be missed. The farm where we had lunch gave you a true and sincere experience of Italian family. I'm surprised that this tour is yet to be rated on Viator.”

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