Italy · WINE TASTINGS IN SIENA
Every itinerary has one free day too few. These 9 wine tastings in Siena earn the slot, priced and timed so you can decide quickly and get back to planning the rest.
Florence to Tuscany in one day: Siena, Chianti with 5 tastings and lunch, then San Gimignano towers. Guided, small-group tour.
“The guide was very informative and engaging. We had a fantastic day and got what we wanted, history, fantastic surroundings and wine yard.”
Small-group Brunello day trip from Siena: 3 winery tastings, family lunch, Sant'Antimo abbey, and free time in Montalcino.
“A very good tour, with a fine lunch and excellent wine. Our guide, Sara, was warm, welcoming and well versed about the region, vineyards, wineries, and wine produced in Montalcino. We were served three selections from Tricherci, a table wine, rosso and brunello. We enjoyed them all as well as noting the differences between them. The others on our tour provided good company for a fine day.”
Half-day Chianti tour from Siena with a small-group minivan ride, Castellina and Monteriggioni stops, plus two winery tastings.
“Fabulous tour with great local insights into culture, wine and food. Highly recommended”
Small-group day trip from Florence to Siena, Chianti wine lunch, and San Gimignano towers, with a guided walk and free time.
“Lorenzo was a fantastic guide and Francesco was a great driver. We had a fantastic time on this tour and loved visiting Sienna, San Gimignano and the Tuscan countryside! Molto bene!”
A 2-hour Chianti Classico tour at Fattoria di Montemaggio, tasting 5 wines plus olive oil and grappa with an English guide.
“Amazing tour, great wine. Francesco is a really nice guide and extremely involved with the winery.”
Brunello di Montalcino from Siena: small-group minivan tour with vineyard walks, cellars, Sant’Antimo Abbey, and a family lunch.
“Paolo is an excelente guide . He is knowlegdeable, pleasant, and great driver . Time went fast. We will book the activity again !”
Full-day small-group Tuscany trip from Siena: San Gimignano, Chianti tastings, Val d'Orcia views, and Brunello in Montalcino.
“I think its too much for one day. I heard everyone in my group say going to Montalcino was not worth the time”
Hands-on cooking in a Chianti farmhouse near Siena: small-group pasta and tiramisu with a multilingual chef, plus included meal and wine.
“We truly enjoyed our cooking class with Simone. He was a great teacher & very patient. We made ravioli with spinach & ricotta & tiramisu. Then we had that for lunch with some bruschetta & Simone's wine. It was a very enjoyable time. We missed our class on the day it was booked because we got lost(follow the directions that they send you!!). Simone was so kind to fit us in the following day. There were just 4 of us in the class so it was great. Loved the setting & loved Simone!!”
Siena organic winery tour with vineyard and cellar walk, tasting 5 wines, plus a seasonal Tuscan meal near the city.
“It was an amazing experience. 2nd wine tasting in Italy, the best so far! The moment you arrive, you’re greeted with stunning views and a warm, welcoming atmosphere. But the real highlight here is the food and wine. The meals are made with the freshest local ingredients, and every dish feels like a celebration of Tuscan cuisine. Each course was perfectly paired with their exquisite wines, produced right on the estate. The wine tasting experience is a must-do—rich, flavorful, and thoughtfully curated, giving you a real taste of the region’s terroir. Whether you’re a seasoned wine connoisseur or just a casual enthusiast, you’ll find something to fall in love with.…”
Every kind of day out in the country, and the best of each.
