5 Winery Tours in Florence Worth Booking

1.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 10,071 reviews · 5 - 5.5 hours · from $41Our pick

Travel by comfortable coach from Florence to two Chianti wineries for guided tastings, vineyard walks, and samples of cheese, salami, bread, olive oil, and balsamic vinegar. Guides such as Anna, Alex, Martina, and John have been praised for bringing Tuscany’s wine, villages, and farming traditions to life. Expect about 5 to 5.5 hours, with no hotel pickup or lunch.

“The tour was great. We had first a visit to a traditional small vineyard from a Italian family, great wine and food, and the Nona was super nice with us. We saw the grapes plantations, drank wine and they were good and had snacks. Second one was way bigger, so more comercial, but it was super cool to see the difference between them, specially cause the second one was more than 100years old. The guide knew a lot about the region, and she even gave us recommendations about Florence. Everything went well”

Check availability →Read our full review

2.Siena, San Gimignano, Pisa & Lunch at Winery

★★★★★★★★★★4.8 · 4,538 reviews · 12 hours · from $112

Spend 12 hours touring Tuscany from Florence by air-conditioned coach. Walk Siena with a local guide, visit its Duomo, enjoy a farmhouse lunch and four-wine tasting at a Chianti winery, then explore San Gimignano and Pisa. Guides such as Sara, Alessandro, Alex, and Giancarlo are known for lively commentary and careful timekeeping.

“The tour was amazing! We had Alex as our tour guide and he did an incredible job. From the minute we drove out of Florence he spoke to the history of every city we visited and everything we saw on the way there. This was perfect as it gives context to what you’re seeing. Everything on the tour was very well thought out, we couldn’t be any more pleased with how everything went. I would strongly recommend 100%. Thank you Alex!”

Check availability →Read our full review

3.Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

★★★★★★★★★★5.0 · 1,007 reviews · 7 hours (approx.) · from $229Top rated

Meet at Piazza della Calza at 9:45am for a 10am departure in an air-conditioned minibus. Visit two wineries near San Gimignano, taste Chianti, Vernaccia, rosé, and more with Tuscan food pairings, then enjoy 1.5 hours in town. Guides such as Emanuele, Valentina, Giovanni, and Ottavio lead the day.

“One of the best winery/Tuscany tours available. Our guide/driver was outstanding. Punctual, courteous and very knowledgeable about the wines and wineries that we were going to visit. He also took us to San Gimignano and shared with us the history of the town. This tour is a must!”

Check availability →Read our full review

4.Chianti Wineries Tour with Tuscan Lunch and San Gimignano

★★★★★★★★★★5.0 · 793 reviews · 8 hours (approx.) · from $229

Spend about eight hours with a guide such as Lorenzo, Daniel, Christian, or Cecilia, visiting two Chianti wineries, tasting several local wines, eating a Tuscan lunch, and wandering San Gimignano. Round-trip transport from central Florence keeps the day simple, while a stop at Piazzale Michelangelo adds a fine city view.

“Enriching experience with a professional and fun staff who paid attention to everyone’s needs. The entire tour was extremely well handled and my wife and I could not been any more pleased. Breath taking views and with detailed guide information by Leonardo is a must. The wine tasting staff were very accommodating and taught the small group how to taste and observe the quality of the wines. Learning, laughter, and scenery was an amazing experience. Thank you so much to the “Fun in Tuscany,” especially Leonardo who really went the extra mile to ensure all we’re having a great time.”

Check availability →Read our full review

5.Chianti Delights: A Tale Of Two Wineries With A Vineyard Dinner

★★★★★★★★★★4.0 · 324 reviews · 7 hours 30 minutes (approx.) · from $106

Leave Florence at 2:45 pm for Siena, then continue through Chianti to two rustic wine estates. Expect free time in Siena, tastings of wine and olive oil, and a Tuscan meal with up to four wine pours. Guides such as Ana, Diego, Lisa, and Frederick have led recent departures, though the exact winery setup can vary.

“Siena was really nice to see, a very unusual city. Enough time to Rome around. Wine tasting and dinner were very nice and relaxed.”

Check availability →Read our full review