Small group Chianti-side wine tour with Mercedes V class Van

Tomasso was our driver and he was amazing. We enjoyed his knowledge of the areas he took us to and his knowledge of the history. He stopped at several places during our journey for photo opportunities.

We spent a wonderful day in the Tuscan countryside with Tomasso as our guide. We are a group of 2 couples. Tomasso was very personable and funny. He gave us interesting historical information about the different areas we visited. He also shared personal family stories. We loved hearing these stories. It made Tuscany really come to life for us. We loved walking the hilly streets in Montalcino…even beautiful in the rain. Ate a delicious lunch at Podere il Casale…Bought some pecorino cheese and farm made balsamic from the farm shop. Pienza was quaint and so pretty. Tomasso took us to his favorite gelato shop there. Yummy!! We made several stops as we made our way through the Val D’Orcia to get pictures. Tomasso took us to Bagno Vignoni to see the thermal pool. And shared a story about his grandparents and that village. The Tuscan countryside is always amazingly beautiful, but the best part of our day was our interaction with Tomasso. We could tell how very passionate he is about where he lives. And we loved that he shared that passion with us. We made a friend that day. We chose Bespoke Italian Tours this time because we knew them from a previous trip. And we will definitely choose them again! I will just say that this was a “wine” tour. However we only had one wine drinker in our group. That really didn’t matter. Bespoke will create an itinerary that suits whatever you may be looking for. And you will have the best experience.

Review: An Unforgettable Journey Through the Heart of Tuscany Rating: ★★★★★ If you are looking for the quintessential Tuscan experience, look no further than Bespoke Tours. Our family of six spent a spectacular day with Tommaso, and it was, without a doubt, the highlight of our trip. The Experience Traveling as a large group can often feel cramped, but we fit perfectly into a spacious, pristine Mercedes van that kept us comfortable as we wound through the rolling hills. We explored Siena and San Gimignano, with the stunning Tuscan countryside providing a world-class backdrop at every turn. Our Guide: Tommaso Tommaso is a true gem. He doesn’t just recite facts; he is absolutely filled with the history of the region. His deep knowledge of the towns and villages brought the stone walls and piazzas to life. Beyond his expertise, it was his warmth and genuine engagement that truly set the day apart. He has a way of making you feel like a guest rather than a tourist, sharing personal stories and recommendations—from the best authentic pasta to the most incredible gelato—that you simply won't find in a guidebook. The Highlights • The Vineyard Lunch: We enjoyed an outstanding four-course lunch at a boutique vineyard. Each course was perfectly paired with one of four exquisite wines, making for a relaxed and indulgent afternoon. • Flexibility: One of the best parts of the day was Tommaso’s adaptability. He was incredibly flexible with our itinerary and personal timing, never making us feel rushed and ensuring the day unfolded at a pace that suited our family. We cannot recommend Tommaso and Bespoke Tours highly enough. If you want a day filled with beauty, history, and a touch of local soul, this is the tour to book!

Tomato was an outstanding guide who took us to Siena and San Gimignano. From the very beginning, he was cheerful and engaging, giving us a genuine feel for life in Italy, especially Florence and Tuscany. He made the entire experience fun and effortless with his charming personality. What really stood out was his deep knowledge of the cities and their culture; we learned so much more than we would have on our own. Having Tomasso as our guide truly elevated the whole trip. Guiliano also helped so much to put it all together. Highly recommend !

We visited two wineries- La Salla a small 2,000 bottle winery, and Castel di Gabbiano, a 900k bottle winery. Both were great experiences! Our driver for the day was Tommaso, an experienced driver and wonderful spokesperson for the Chianti area.

We enjoyed having a comfortable ride to the wineries and ample tastings with a small group. The provided lunch was really more of a snack during the first wine tasting (cheese, meat, and bread), so we should have eaten lunch first. While all of our tour guides were kind, one of them seemed to have just memorized the “script” and it felt very rote and impersonal. Overall we enjoyed our trip but wish it been clearer about the lunch situation and having a more personalized experience.

Nothing but spectacular! Guliano curated a most wonderful 9 day tour for my family. 3 days in Rome, including a Rome/Milan Soccer Game… The guides were great and having Guliano drive us to and from all tours was most helpful and efficient. The Tuscany part of our trip included absolute Gems each day. Guliano was our driver and guide. He knows the area so very well….off the beaten path boutique wineries, restaurants, vistas..,amazing. It was very personalized. His mother was our guide in Florence…not only incredibly knowledgeable, perfect English but she was also a delight! We finished on the Tuscan Coast upon Guliano’s recommendation. The Hotel and Restaurants did not disappoint-it was stunning. Guliano is very knowledgeable about the history and nuances of each area, which makes the experience very educational as well as fun. He is genuinely personable and delightful to spend time with. 5 Star Experience for sure!! I highly highly recommend Bespoke Tours Theresa Bruno

Soooo our tour guide 100% forgot about our tour. We called and he immediately apologized and realized it was a mistake on their part. Long story short, the tour guide gave us multiple options to make up for the mistake and we ended up having the best time of our lives! It was a completely private wine tour experience with one winery with tasting (wine, cheeses, olive oils) overlooking a beautiful countryside and one private wine tasting in a wine cellar. Afterwards we had dinner at a nice restaurant in a beautiful village! We were picked up and dropped off where we needed to be and on time. We could not have been more pleased with our experience! Just know if the tour accidentally forgets about your tour they will 100% make a massive effort to make sure your experience is enjoyable. HUGE thank you to everyone! Grazie mille!

Today was incredible! We visited two different vineyards that were very unique in their experiences! The staff at each location was knowledgeable with the wines and the history of their property. This is an excellent way to see Tuscany’s wine region!

Niccolò our tour guide was amazing! We had such a great time touring the local wineries and learning the history of the Tuscany region.