From Siena Tours

TUSCANY

10 Best From Siena Tours In Tuscany

Tuscany's standouts.

The 10 from siena tours travellers book most often across Tuscany. Each one with the price you pay, the operator behind it and the day you actually get when you turn up.

10 Best From Siena Tours In Tuscany

From Siena: Chianti and Castles Tour with Wine Tastings

From Siena: Chianti and Castles Tour with Wine Tastings - Castellina in Chianti and Monteriggioni: towers, walls, and that Tuscan walk

1.From Siena: Chianti and Castles Tour with Wine Tastings

Most Popular★ 4.6

Half-day Chianti castles and wine tastings from Siena with a small-group minivan, two winery stops, and scenic hilltop towns.

“The guide was wonderful and explained to us all the places we were going to visit. We stopped in small towns along the way that were very picturesque and scenic, which really added to the atmosphere. The wineries were amazing and the wines were truly excellent — I enjoyed every moment.”

631 reviews5 hoursFrom $100by My Luxury Drive

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From Siena: Tuscany Hills Wine Tour

From Siena: Tuscany Hills Wine Tour - Monteriggioni and Chianti: the drive that makes the wine taste better

2.From Siena: Tuscany Hills Wine Tour

★ 4.1

Full-day Siena wine tour to Monteriggioni, Pienza, and Montepulciano with two tastings of Chianti and Nobile, plus free time in town.

“The tour was wonderful! It was really more about seeing the three towns than about food. The bus was modern and comfortable. The guide was very nice. We were basically left on our own to explore which was very nice. I recommend it.”

323 reviewsFrom $146.14by My Tour in Italy

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Hot Air Balloon Flight Over Tuscany from Siena

Hot Air Balloon Flight Over Tuscany from Siena - Safety briefing, crew coordination, and what to watch for

3.Hot Air Balloon Flight Over Tuscany from Siena

★ 5.0

Hot air balloon flight over Tuscany from Siena with small-group views, a sparkling wine toast, and a croissant picnic breakfast.

“Mornings can be cold so bring layers. Balloon team were professional and attentive to everyone’s experience. If you pay for pick up service, be sure you know how to use WhatsApp to be able to contact the driver in the morning.”

129 reviews3 hours (approx.)From $374.91by Balloon Team Italia

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Vespa Tour with Lunch&Chianti Winery from Siena

Vespa Tour with Lunch&Chianti Winery from Siena - Getting to the Start: Where You Meet and What to Watch For

4.Vespa Tour with Lunch&Chianti Winery from Siena

★ 4.0

Ride a Vespa through Chianti hills from Siena, stop in medieval towns, and enjoy a winery tour with tastings plus a light lunch.

“This day was amazing!!!! There are some things you should know before hand. It doesn’t leave from Siena. It is a little town about 20 mins away. If you don’t have a car you need to spend the extra for pick up and drop off. I didn’t see that until the night before and we…”

126 reviewsFrom $168.36by myTour in Italy

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Tuscany Hiking Tour from Siena Including Wine Tasting

Tuscany Hiking Tour from Siena Including Wine Tasting - The hike in Tuscany: olive groves, vineyards, and those plant facts

5.Tuscany Hiking Tour from Siena Including Wine Tasting

★ 5.0

Hike part of the Via Francigena from Siena to Monteriggioni, then enjoy a guided wine tasting in a walled hill town with a return ride included.

“Our guide shared impressive knowledge of the history and nature of the area. Comfortable pace and delightful wine tasting experience at the end.”

112 reviews4 hours (approx.)From $72.56by Tuscan Escapes by Papilio SRL

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From Siena/Chianti: Dinner & Drinks in the Chianti Vineyards

From Siena/Chianti: Dinner & Drinks in the Chianti Vineyards - The farm and winery stop: where your wine education becomes practical

6.From Siena/Chianti: Dinner & Drinks in the Chianti Vineyards

★ 4.0

Chianti vineyard dinner from Siena with sunset aperitif, winery walk, and candle-lit 4-course Tuscan meal with wine.

“Really enjoyed this experience. For Italy its a bit pricey but actually for Tuscany the price is somehow fair/even cheap, as the region is a bit more than other regions. The main negative was it was a little rushed. They could take longer and slow down the experience. Personally I would have also liked to…”

95 reviewsFrom $123.48by My Tour in Italy

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Small-Group Chianti Trip with Wine Tasting from Siena

Small-Group Chianti Trip with Wine Tasting from Siena - Getting out of Siena: the minivan ride and what the guide adds

7.Small-Group Chianti Trip with Wine Tasting from Siena

★ 5.0

Small-group Chianti castles day trip from Siena with tastings at Castello di Brolio and Castello di Ama plus a full Tuscan lunch.

“Daniel was very informative. A little disappointed that after 5 hours on a wine tasting trip we had had only one taste of wine. When we arrived at the 2nd winery...it would have been nice to have been given a taste while listening to how wine is made. Wish we knew lunch was not going…”

72 reviews8 hours (approx.)From $217.22by Tuscan Escapes by Papilio SRL

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From Siena: Chianti and San Gimignano Sunset Tour

From Siena: Chianti and San Gimignano Sunset Tour - Meet Under San Domenico Basilica and Enjoy the Small-Group Ride

8.From Siena: Chianti and San Gimignano Sunset Tour

★ 4.8

Small-group Chianti tasting, Monteriggioni fortress, and San Gimignano towers at sunset, finished with a farm dinner and wine.

“Eleanor was wonderful. Knowledgeable and fun. The vineyard visit was amazing. It was great to see Monteriggioni and San Gimignano without having to rent a car. The dinner and wine we had was delicious. Highly recommend.”

67 reviewsFrom $203.91by Tuscan Escapes by Papilio

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Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch

Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch - Getting behind the wheel: manual gears, license rules, and real safety expectations

9.Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch

★ 4.5

Drive a vintage Fiat 500 from Siena through Chianti to Monteriggioni and a winery for tasting and a 3-course Tuscan lunch.

“All! The Fiat and Vespas and two guides. All friendly and created a great time. GREAT JOB!! Route was scenic and explanation of where we were and wine tasting and food were very well thought out.”

52 reviewsFrom $191.58by myTour in Italy

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From Siena: Chianti Countryside E-Bike Tour w/ Lunch & Wine

From Siena: Chianti Countryside E-Bike Tour w/ Lunch & Wine - The 20km Chianti Ride: What the Route Feels Like Over 6 Hours

10.From Siena: Chianti Countryside E-Bike Tour w/ Lunch & Wine

★ 4.8

Guided e-bike ride from Siena through Chianti, with a medieval Monteriggioni fortress stop and a farm lunch with wine.

“Dom was a fantastic guide. The E bikes were great quality, the ride was beautiful and scenic and the winery experience was so lovely. The Wine maker was knowledgeable and friendly and Dom gave us lots of interesting facts and laughs throughout the day about the Tuscany Region. Perfect day out! Did I say the…”

44 reviewsFrom $203.91by Tuscan Escapes by Papilio

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