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“Leo was our guide and he was knowledgeable, courteous and funny, everything you want in a guide. The hosts and hostesses were wonderful. Simoni and Lucia were the best. Time and money well spent.”
Experience authentic organic Chianti wines with stunning vineyard views, expert guides, and delicious local snacks on this immersive two-hour tour in Tuscany.
“The wine’s were excellent but if you have food intolerances the food was fair.”
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.
“Great value - generous pours and lovely large lunch! We enjoyed being in the vineyards as well as the fermentation room”
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.
“Wonderful trip through Tuscany with beautiful scenic views, stops at two charming Tuscan towns, and a delicious meal at a farm. Our guide Billy was very informative and a lot of fun. He went out of his way to make sure I could join the…”
Discover Tuscan wines through an engaging 2-hour class in Siena, learning from local experts, tasting regional wines, and pairing with delicious bites.
“Very educational, and with a good portion of humor! Everyone in the class received a portion of personal attention.”
Experience a hands-on Brunello wine region cooking class on a scenic Tuscan vineyard terrace, combined with castle tours and wine tasting near Siena.
“This was the best day ever! We cooked 4x dishes (1x appetiser, 2x pasta, 1x dessert) and these were paired with 3 wines, plus we had a 4th wine while we cooked! Cooking and having lunch overlooking the winery was magical! The castle/fortress tour was…”
Discover Tuscany’s best with this small group Chianti and castle tour from Siena, featuring visits to two wineries, picturesque villages, and stunning views.
“Both wineries had excellent wine tastings with knowledgeable and friendly hosts. Our guide did a great job describing the Chianti region and history. The town and castle were highlights too.”
Discover Tuscan charm on this full-day tour visiting San Gimignano, Siena, and Monteriggioni with wine tastings, lunch, and expert guides from Florence.
“Just a nice time. Constantino ( I believe that was his name) was informative, passionate and funny. Much Enjoyed lunch and wine in Tuscany winery. The only (small) issue I had was the tour had English and Spanish translation. You should separate the 2 audiences…”
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.
“Wonderful trip with a great tour guide Veleaka. This was an 11hr tour and we were never bored. It was a leisurely trip with the best views of Tuscany we saw while in Italy.”
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.
“Our tour guide was great! We were a tad disappointed with the winery because they didn’t provide a full wine tasting. They only provided 2 glasses and it was not of the most famous Chianti bottles. Other than that the winery was beautiful and the…”
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.
“Fabulous! Great guide, perfect weather (late October), great like minded group of hikers. Was a good few hours (almost 4) of hiking but fairly flat and not a fast pace. Definitely recommend. The town of Monterriggioni at the end was the icing on the cake.”
Discover Tuscany’s finest Brunello wines on this small-group tour visiting two historic wineries with tastings, scenic drives, and a delicious pairing lunch.
“Excellent from start to finish. Everything was on time and lots of good wine to buy to send home. So much fun!”
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.
“Our tour guide Mohad was incredibly knowledgeable, not only about Siena’s history but also about all the food, wine and gelato places. Some of them truly hidden gems! Perfect mix of walking tour and tasting of local specialties, all within 3 hours and away from…”
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.
“This was a great wine tour! It was just the right amount of time spent at each winery and city to give you the opportunity to experience and explore the culture and wine. We stopped at 2 wineries with tastings, and a store tour winery…”
A striped Duomo, a shell-shaped square and Brunello next door.