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Reviews

• 10/10 Would Do It Again

  jessiep793,May 27, 2026

  - Review from Tripadvisor

  5.00

  The tour was fantastic. The wineries were amazing, and our driver, Massimo, was so knowledgeable and a great guide throughout Tuscany. He curated the day perfectly—each stop felt unique, from intimate family‑run vineyards to stunning estates with unforgettable views. We also loved having time to explore San Gimignano, which was such a fun addition to the day. Wandering through the medieval streets, grabbing gelato, and popping into the little shops made the experience feel even more special. We never felt rushed, and Massimo’s insights into the region’s history, wine production, and local culture made everything come alive. The tastings were generous, the wines exceptional, and the entire day felt effortless and beautifully organized. It was truly the highlight of our trip.

  

  

• A perfect Tuscan day!

  Carleen P,Apr 3, 2026

  - Review from Viator

  5.00

  Massimo was the best! He was so knowledgeable and so accommodating. And the wineries we visited were awesome. Beautiful views, delicious food, and great local wines, olive oils, etc. Just a wonderful day.

• Massimo Made Tuscany Unforgettable

  Alex W,Oct 9, 2025

  - Review from Viator

  5.00

  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.

• DO THIS TOUR!!!

  Kevin U,Nov 10, 2024

  - Review from Viator

  5.00

  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.

  

  

  

  

  

• Cruise excursion to Tuscany

  Jacqueline W,Sep 19, 2024

  - Review from Viator

  5.00

  This was the highlight of our whole trip. Massimo was the best guide we could have asked for. He was friendly, engaging, & very knowledgeable about wines & all things Tuscany! He helped us fall in love with Tuscany & we will definitely be back. The wineries he took us to were family owned & gave us the most amazing personal attention. The wines spoke for themselves as they were some of the best I’ve ever tasted. Would highly recommend this tour!

• Wines and Dined in Tuscany

  jerryr872,Mar 16, 2024

  - Review from Tripadvisor

  5.00

  This tour made for a very special day. Our fabulous driver brought us to small towns and wineries that we would never have thought to visit. Gave us a real sense of local history. Wineries were friendly and tasty!

  

  

  

• A Day to Remember

  Julie B,Nov 13, 2022

  - Review from Viator

  5.00

  We had the most wonderful day with Massimo! He was our driver/guide/sommelier and now a friend! He carefully selected the wineries that we attended and they did not disappoint! The people at both wineries were so lovely!! Beware, the “light” lunch is so delicious and not so lite!! The wine was exactly as we like it and although we know a little about wine, we learned more!! Massimo’s passion for wine and Tuscany made our day extra special! The van was comfortable. I would recommend even for two couples with the same taste in wine. San Gimignano was beautiful and quaint. The shopping was a great variety of quality and truckers. But the world famous gelato, oh my!! My husband and I highly recommend a day in the beautiful Tuscan countryside with Massimo!

• Amazing Personal Wine Tour

  anaroseg,Jul 30, 2022

  - Review from Tripadvisor

  5.00

  Our Tuscany wine tour was the highlight of our vacation. We shared the experience with another couple on our cruise ship, and it was one of the best experiences we had on an amazing vacation. Our tour guide was waiting for us upon arrival, and whisked us away in an air conditioned van to San Gemignani. Fun and informative, we made our way through the countryside for some of the best Gelato on our entire trip. But the wineries (and food) were the real experience. Our first stop couldn't have been more perfect - a private wine tasting and meal cooked on a small family winery. You have to save room, because the cellar wine tour on the 2nd stop ends with even more tasty treats and more amazing wine. If you are looking for a private wine tour from Livorno - this is it.