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

Montalcino trip to San Fallippo winery private tasting

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.

via Tripadvisor

Best Day in the Val D’Orcia

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.

via Tripadvisor

Unforgettable Family Journey through the heart of Tuscany

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!

via Tripadvisor

Wonderful Tuscan Experience

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 !

Response from the operator: Thanks for the kind words! We'd love to tour with you again! Grazie

via Tripadvisor

Wine tasting in the Chianti region.

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.

via Viator