From Siena: Chianti and Castles Tour with Wine Tastings
1.From Siena: Chianti and Castles Tour with Wine Tastings
Half-day Chianti castles and wine tastings from Siena with a small-group minivan, two winery stops, and scenic hilltop towns.
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: Tuscany Hills Wine Tour
2.From Siena: Tuscany Hills Wine Tour
Full-day Siena wine tour to Monteriggioni, Pienza, and Montepulciano with two tastings of Chianti and Nobile, plus free time in town.
“The mixture of two winery visits and tastings, along with two beautiful towns and the scenery.”
Hot Air Balloon Flight Over Tuscany from Siena
3.Hot Air Balloon Flight Over Tuscany from Siena
Hot air balloon flight over Tuscany from Siena with small-group views, a sparkling wine toast, and a croissant picnic breakfast.
“Wonderful experience, even I had to wake up at 5am. We had to change the departure from Siena to Florence, because of the weather conditions. The way from Relais Toscano, Asciano (Siena province) was very foggy, but we managed to be in time.”
Vespa Tour with Lunch&Chianti Winery from Siena
4.Vespa Tour with Lunch&Chianti Winery from Siena
Ride a Vespa through Chianti hills from Siena, stop in medieval towns, and enjoy a winery tour with tastings plus a light lunch.
“The tour itself was great. However, a Fiat 500 in our group was having mechanical issues, and we spent a large part of the tour waiting on the road for the car to be exchanged. This led to us missing all of our stops except the one at the vineyard. The vineyard was great, anRead…”
Tuscany Hiking Tour from Siena Including Wine Tasting
5.Tuscany Hiking Tour from Siena Including Wine Tasting
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.
“This was a great way to see the beautiful Tuscan countryside. Our guide, Keko, provided lots of history and interesting information about the region. This is an easy 5 mile hike that ends in the cute town of Monteriggioni. There’s not much to the town but we sampled a couple of good Chianti wines.”
From Siena/Chianti: Dinner & Drinks in the Chianti Vineyards
6.From Siena/Chianti: Dinner & Drinks in the Chianti Vineyards
Chianti vineyard dinner from Siena with sunset aperitif, winery walk, and candle-lit 4-course Tuscan meal with wine.
“amazing, would really recommend this if you want good food, amazing wine and excellent staff who will teach you alot about the wine and how to taste it. thank you so much for the wonderful evening”
Small-Group Chianti Trip with Wine Tasting from Siena
7.Small-Group Chianti Trip with Wine Tasting from Siena
Small-group Chianti castles day trip from Siena with tastings at Castello di Brolio and Castello di Ama plus a full Tuscan lunch.
“Very thoughtful itinerary with a knowledgeable guide. Marco was great! We learned about winemaking, the Chianti Classico region, and its people. Lunch was amazing and beautifully presented.”
From Siena: Chianti and San Gimignano Sunset Tour
8.From Siena: Chianti and San Gimignano Sunset Tour
Small-group Chianti tasting, Monteriggioni fortress, and San Gimignano towers at sunset, finished with a farm dinner and wine.
“Guillermo was an absolutely fantastic guide! His knowledge of the history was impressive, and he brought each story to life in a way that made the experience truly unforgettable. He was also incredibly attentive to all of us, ensuring everyone felt comfortable and engaged throughout the tour. I can't recommend Guillermo highly enough—if you're looking…”
Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch
9.Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch
Drive a vintage Fiat 500 from Siena through Chianti to Monteriggioni and a winery for tasting and a 3-course Tuscan lunch.
“Of course, 1960s Fiat makes for an interesting challenge…and yes you can smell gas, but we LOVED this experience! The guide and other guests were so much fun. We bonded over laughs and poking fun at some lackluster driving moments, but this made for an experience we’ll never forget! The scenery, towns and wineries were…”
From Siena: Chianti Countryside E-Bike Tour w/ Lunch & Wine
10.From Siena: Chianti Countryside E-Bike Tour w/ Lunch & Wine
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…”
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