Siena · CHIANTI CLASSICO WINE TOURS & TASTINGS
23 reviewed
Chianti Classico is the closest wine country to Siena and the easiest first cellar day. These are the 15 best tours into the black-rooster hills, with the wineries and castles each one reaches, how generous the tastings run, and what to pay.
Full-day small-group Florence trip to Siena, Chianti wine tastings with lunch, and San Gimignano towers, with free time to wander.
“Definitely a recommend! Our guide gave useful tips on the way to the destinations and wine tasting was one of the highlight! We liked everything about the day trip!”
Half-day Chianti castles and wineries from Siena with a small van, hilltop villages, two tastings, and Tuscan bites for $100.
“Absolutely amazing, such a pretty way to experience Chianti. Love the small 8 people group. The first winery ( Poggio ai Laghi) was fabulous, and the second (Lornano) was quaint. We really enjoyed it and would recommend!”
Small-group Chianti trip from Siena with two winery visits, 7 wine tastings, olive oil sampling, and medieval village time.
“The tour was fantastic! Loved both wineries and the stops in the villages. Worth every penny! Our tour guide was great.”
Hands-on cooking in a Chianti farmhouse near Siena. Make bruschetta, fresh pasta, and tiramisù with wine and a recipe card.
“Beautiful setting in the Tuscan countryside. Chef Simone was very helpful and made it a great experience for everyone.”
Cook Tuscan classics in a Chianti farmhouse with chef Simone: ravioli, tiramisu, and wine in a 4-hour small-group class.
“The highlight of our trip. Chef Simone made us feel so welcome and we thoroughly enjoyed our cooking class set in the Tuscan Hills.”
Taste organic Chianti at Fattoria di Montemaggio: vineyard and cellar walk, five wines with olive-oil snacks, led by Francesco.
“Passionate staff providing deep insights about winemaking: it's been tremendously enlightening. The presenter truly took his time explaining and letting us taste the wines. Outstanding wines of great quality and high price have been provided to us.”
Vespa day trip from Siena to Chianti: guided convoy, winery tour and tasting, light lunch, and town stops like Monteriggioni.
“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 arranged Read more”
Greve in Chianti wine tasting at a family-run winery: vineyard history, olive oil samples, four red wines, and local snacks in English.
“Maurizio, il titolare della omonima cantina Brogioni, ci ha accolto con un affetto ed una cordialità eccezionali, tra l'altro minimizzando il nostro ritardo dovuto ad un inconveniente con l'auto. Con due parole ci ha messo a nostro agio e ci ha fatto dimenticare i nostri affanni. Ci ha raccontato con passione e trasporto prima la storia del Chianti (inteso sia come zona sia come vino) poi della sua tenuta. Una storia di un uomo follemente innamorato del suo lavoro che, in mezzo alle peripezie dovute alla perdita del padre in età giovanile, e della conseguente vendita della tenuta originaria, è riuscito passo passo a creare una tenuta tutta sua. Tenuta…”
Siena food and wine walking tour with gelato, sparkling Prosecco-style wine, and a classic Osteria lunch plus Chianti. Small group, 2.5 hours.
“Was a very small group so very intimate. Angie was a great guide. We were late because of confusion with our bus and then needing to get taxi. The tour operator was able to support us to catch up with Angie and the other participants so we did not miss out. Very informative tour on the location as well as the food and wine. Very enjoyable. Highly recommend this tour company. .”
Aperitif at sunset and a candle-lit 4-course Tuscan dinner in Chianti vineyards, plus winery tastings and wine with a Siena pickup.
“Valeska was a great guide!! The wine was wonderful, as was the food! 10/10”
Small-group Chianti day trip from Siena to Castello di Brolio and Castello di Ama, with lunch and wine tasting included.
“learned so much about the region and the history. the food and the wine were amazing as well. Loved out tour guide and would highly recommend!!”
Chianti wine tastings plus a paired lunch in San Gimignano, with comfortable van pickup from Siena and a medieval town stroll included.
“I have to say that my favorite part of this spectacular tour was meeting Sella at Monte Chiaro winery in Monteriggioni. Not only are the wines here outstanding but her love of wine, and regional foods are unmatched. She brings the wines to life with her presentation skills and we were sad to leave her. Sella says that "wine is food" and full of vitamins and nutrients. So, she has confirmed for me that wine for breakfast is a perfectly good way to start the day!”
Small-group Chianti and San Gimignano sunset tour from Siena with winery tasting, Monteriggioni fortress, and Tuscan farm dinner with 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.”
Small-group sunset trip from Siena to Chianti and San Gimignano with winery tastings, Monteriggioni walls, and farm dinner, max 8, $217.
“The tour was incredible, and our guide Elio was warm, funny, and very informative. He tailored the information to the group’s interests, made sure everyone was enjoying themselves, and was an awesome driver (those roads are no joke!). Our dinner was homemade and beyond delicious (saffron gelato was a surprising delight). Highly recommend!”
Guided e-bike tour from Siena through Chianti to Monteriggioni, with farm lunch and wine. Small group and easy-powered hills.
“This experience was amazing. The bikes were very nice, the tour guide was fantastic and it was a real adventure. The stop for lunch at a winery was a great experience too. 10/10 recommend.”
