Siena
The wine country at Siena’s gates: Brunello tastings in Montalcino, Chianti immersions and the Montepulciano-Pienza loop with pecorino between cellars. Three of Italy’s greatest reds grow within an hour; the designated driver comes included.
Discover authentic Brunello di Montalcino wines on this small-group day trip from Siena, including visits to three charming wineries, a Tuscan meal, and the Abbey of Sant'Antimo.
Most Popular“It was a boutique wine tour! Starting with an educated wine expert, great destinations & great wine, food & views.”
Experience authentic organic Chianti wines with stunning vineyard views, expert guides, and delicious local snacks on this immersive two-hour tour in Tuscany.
“Franceso was great very passionate about the boutique vineyard & explained lots about the history & the area. Wines were delicious & purchases were made to enjoy during the rest of our holiday. Would highly recommend going!”
Discover Tuscany’s wine heritage with a small-group tour from Siena. Taste organic wines, learn from a passionate guide, and enjoy a scenic countryside lunch.
“Best wine tasting we have been to in Tuscany. Everyone was so lovely and the guides were so informative. The wine and food were delicious and we came home with a few bottles of course! Highly recommend!!”
Discover the charm of Tuscany with this small-group day trip from Siena to Pienza and Montepulciano, including wine tastings, a cheese farm, and stunning scenery.
“The tour guide was fabulous, very entertaining. Farm house lunch and villages visited were great. Tour guide was very knowledgeable, fantastic day out.”
Discover Tuscan wines through an engaging 2-hour class in Siena, learning from local experts, tasting regional wines, and pairing with delicious bites.
“The absolute perfect evening! We learned so much about Tuscan Wines. Equal parts informative and so much fun! Can’t wait to do this again next time we visit Siena.”
Experience a hands-on Brunello wine region cooking class on a scenic Tuscan vineyard terrace, combined with castle tours and wine tasting near Siena.
“We took this tour and cooking class with 'Tours of Tuscany' and our entire group agreed it was a top moment of our entire Italy trip! The property where you take the class is one of a kind; a historic building and winery in the…”
Discover Tuscany’s best with this small group Chianti and castle tour from Siena, featuring visits to two wineries, picturesque villages, and stunning views.
“Great tour. The castles and the wineries were great. A lot of different wines to taste, but also gained knowledge of the region and the winemaking process. Just one warning. If you get car sick easily, make sure you bring your remedy. The roads are…”
Discover Tuscan charm on this full-day tour visiting San Gimignano, Siena, and Monteriggioni with wine tastings, lunch, and expert guides from Florence.
“We did this tour with free time in the cities only- no guided tour. Loved the cities and wine tasting. It is a convenient way to get to these cities without having to deal with public trains and busses. We did have some issues understanding…”
Experience authentic Tuscan flavors with a small-group cooking class in Siena. Learn to make pasta, pizza, and tiramisu at a charming Chianti farmhouse.
“This was so much fun! My husband even says he now wants to have date nights and cook fresh pasta at home (while drinking Italian Chianti Classico, of course). Would highly recommend this experience. Everything from the food, to the location, was perfect.”
Discover Tuscany’s highlights on this small-group day trip from Siena, including San Gimignano, Montalcino, and Chianti wine tastings—perfect for wine lovers and history buffs alike.
“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…”
Experience Tuscany's scenic beauty on a Vespa from Siena, visit a Chianti winery, enjoy wine tasting, and savor a light lunch in this full-day adventure.
“What an excellent way to see Chianti I on a Vespa! Fredricho was an excellent guide leading us and stopping @ 3 towns allowing plenty of time to sightsee, shop, and experience the local atmosphere. Stopping @ Casale Dello Sparviero Winery was amazing! Jada was…”
Explore Tuscany on this scenic half-day hike from Siena, including a walk along the historic Via Francigena and a delightful wine tasting in Monteriggioni.
“The hike was awesome. Francesco was amazing. He showed us all the different plant life, talked about his experience with the Via Francigena. He was delightful, full of life and very caring.”
Discover Tuscany’s finest Brunello wines on this small-group tour visiting two historic wineries with tastings, scenic drives, and a delicious pairing lunch.
“Nicola our guide was so nice and full of knowledge about Italian wine, especially about Brunello as he is from Montalcino. He is teaching you from the moment you get in the van. We stopped at a small winery there, tasted 5-6 wines with some…”
Discover Siena’s charm on a guided walking tour with authentic Tuscan food, regional wines, and hidden sights—perfect for lovers of history and cuisine.
“This was honestly one of the best tours I’ve been on, and I’ve done hundreds. Our guide was informative and interesting. We stopped for gelato tasting, wine tasting, and had a delicious lunch of traditional Tuscan cuisine. We saw so much of Siena and heard…”
Discover Tuscany's charm on this full-day Siena-based tour featuring visits to Pienza and Montepulciano, with wine tastings, stunning views, and free time.
“I was not impressed with this tour. The pic with the promo is not what you get. The tour guide was very professional and informative. But, this was not a Tuscan wine tour, far from it. The wine tasting was in a sterile wine factory.…”
A striped Duomo, a shell-shaped square and Brunello next door.