Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno

Our guide, Massimo, warned us not to fall in love with Tuscany. We laughed—how could seven hours make us fall in love? Well, he was right. We stopped in Livorno on our cruise and wanted to go wine tasting in Tuscany. After lots of research, we booked this tour, and while it was expensive, it was worth every penny. It ended up being our favorite experience from our two-week trip. Massimo met us right at the cruise terminal (super easy!) and was incredibly knowledgeable and proud of his country. The drive itself was stunning—we stopped several times for photos—and our visit to San Gimignano was a highlight. The wineries were authentic, family-run gems with amazing hosts, generous tastings, and what was supposed to be a “light lunch” that turned out to be the best meal we had in all of Europe. We can’t recommend Massimo enough. He made the day unforgettable, and we’re already planning our return.

We were in Livorno on a cruise ship stop. We have done numerous cruise booked excursions, but this was by far the highlight of the entire trip. If you want a unique, private experience, and want to avoid the large canned cruise excursions, this is for you. My party of 4 were met promptly at the time scheduled by our Drive and Guide, Massimo. He was extremely funny and friendly. He knew the area intimately and is also a sommelier, which was a huge benefit for any winery tour. After an hour long scenic drive through the Tuscan countryside, we came to our first stop, the beautiful medieval town of San Gimignano. One of the highlights of this was the fact that we beat the large cruise ship tours and were able to experience the town with out the large crowds. They did show up about halfway during our free time in the village, but it was no fault as we had plenty of time to explore and appreciate prior to the larger tours. We then left for about a 30 minute drive through Tuscany heading towards our first stop. During each drive, our guide Mossimo kept us entertained through his knowledge of the area and simply his banter and comedy. We connected so well with him. On this short drive he even found time to stop at a scenic overlook and being that is was olive harvest season, we was even able to show us an olive tree and explain the harvesting processing and we tasted some olives right off the branch. Beware, olives themselves are bitter, but it was till such a great experience. Our first winery, was a "small" family estate and winery. I say small only since compared to larger vineyards their production is small, but their home winery was beautiful. After a tour through their production process and property, we sat in their beautiful dinning room and tasting area where they provide a traditionally Tuscan Italian lunch which was cooked in home by their Nona. It was so much food with delicious pasta, meats, cheeses, local honey, freshly pressed (I mean that morning) olive oil, and of course their delicious wines. They do offer you options to purchase but there was no pressure. The family treated us like family friends and guests. We then had another 30 minute drive to a second winery. This winery was larger in production and definitely went back much further as evident by their amazing wine cellar which had bottles from over 50 years prior. The grounds were just as beautiful and the winery guide was so friendly. They let us try 6 wines here and also provides us some amazing food pairings. They also provided options to buy and ship which were so good, we couldn't help ourselves and place some orders. When the entire day was complete, we were all sad the day had ended. I want to go back and explore the region more, Massimo lives locally in a city called Lucca and he gave such great details of the area, I think I can go back and spend a week there or more. If I have any regrets it is that I wish we bought more of the wines and olive oil and that I wish I had more time to enjoy such a wonderful and amazing area. Please make sure you bring enough cash to tip if you chose and also to pay for the tastings. It is noted in the tour description that the winery tastings are separate, but they are reasonable for the experience you get. It was about $75 Euro per person total. Honestly the experience you get $75 Euro felt like a steal.