The 8 Best Wine Country Day Trips in Florence

1.Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

★★★★★★★★★★5.0 · 21,634 reviews · 11 to 12 hours (approx.) · from $114Our pick

Travel by air-conditioned coach from Florence to Siena, San Gimignano, Pisa, and a Chianti winery. You’ll tour Siena Cathedral, enjoy free time in three towns, and can add a farmhouse lunch with four wine tastings and a Leaning Tower climb.

“We went on this day trip during our honeymoon in October 2025. This excursion was an outstanding experience thanks to our tour guide, Giancarlo. He was engaging, informative, funny, and knowledgeable. Siena, San Gimignano, Pisa, and lunch at the winery were beautiful. It is a long day so be sure to dress comfortably. This day trip was one of the highlights of our trip. We highly recommend going on this tour.”

Check availability →Read our full review

2.Wineries, Tastings, Lunch & San Gimignano Day Trip

★★★★★★★★★★5.0 · 82 reviews · 8 hours · from $223

Spend eight hours in a small group of up to eight, visiting two Chianti wineries, tasting organic wines and olive oils, eating a Tuscan lunch, and exploring San Gimignano. Guides such as Daniel, Christian, Lorenzo, and Guido are praised for their warmth, local insight, and easygoing style.

“Christian was an excellent tour guide. He was friendly and informative and navigated some “difficult personalities” on the tour very well. (These people acted like they were on a private tour and could have easily ruined the trip if not handled well.) He also provided suggestions on where to shop or dine for the remainder of our trip. I would highly recommend the experience.”

Check availability →Read our full review

3.Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Florence

★★★★★★★★★★5.0 · 28 reviews · 8 hours (approx.) · from $430

You’ll leave Florence at 9 a.m. in a private, air-conditioned minivan with a driver such as Marco, Lorenzo, Sam, or Tomasso. Expect San Gimignano, Chianti wine country, and room to add wineries, Volterra, or the American Cemetery.

“Our driver Lorenzo was a fabulous host catering to our specific location requests with good humour, wit and knowledge about the region, history and politics. Highly recommended if you have specific destinations in mind or would prefer someone else to take charge.”

Check availability →Read our full review

4.Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Florence

★★★★★★★★★★5.0 · 10 reviews · 8 hours (approx.) · from $413

Leave Florence with Marco or another Tuscany Top Drivers guide for a private eight-hour outing to San Gimignano and Chianti. Expect a comfortable minivan, hotel pickup, medieval towers, country roads, and possible winery visits. Food, drinks, and tasting fees are extra.

“A great introduction to the chianti region. Beautiful. And Marco was super nice, helpful and informative. San Gimignani was very unique and the wine experience at Casa Emma was fantastic. Whatever you want to do in Tuscany - I highly recommend working with Marco!”

Check availability →Read our full review

5.Half Day Tour Chianti Winery with San Gimignano

★★★★★★★★★★4.5 · 5 reviews · 5 hours (approx.) · from $348

You’ll travel from Florence in a climate-controlled minivan to San Gimignano and Casa Emma winery. Guides such as Mario, Andrea, or Benjamin handle the driving and commentary, while Cristina may lead the tasting. Expect a compact, private tour with wine, hill-town views, and limited free time.

“This tour is not at all what my husband and I were expecting. We had hoped to have some time to explore San Gimigano on our own but felt rushed. We walked with our guide up the Main Street in town and stopped in the first piazza. We asked to stop by the famous gelato establishment but were told “No, I don’t recommend this”. We barely had time to purchase a souvenir before leaving. There were moments when we felt the driver drove too fast and we didn’t learn anything regarding the history of the area. The language barrier was an issue for us as well. The highlight of the…”

Check availability →Read our full review

6.HALF-DAY Tour to Chianti Wine Region: CHIANTI COLORS & FLAVORS

★★★★★★★★★★3.5 · 3 reviews · from $141

Travel by air-conditioned coach from Florence into Chianti, where an expert multilingual escort leads you through two wineries. Taste seven wines with Tuscan appetizers, olive oil, and balsamic vinegar, then browse local products and enjoy time among vineyards and cypress trees.

“The tour description was for a small group experience (max 20 people) to visit the ancient city of Greve and two wineries. Upon arriving at the tour meeting point we were ushered onto a bus with at least 50 people, not the max 20 as Read more”

Check availability →Read our full review

7.day trip to Montalcino with 2 Wineries and Lunch

★★★★★★★★★★5.0 · 2 reviews · from $293

Travel from Florence by van with an English-speaking guide to two family-run Brunello wineries. Tour cellars, taste Rosso and Brunello di Montalcino, eat a local Tuscan lunch, and explore Montalcino’s medieval center in a group of up to eight.

“It was a great day! We spent a lot of time looking into different options, but settled on this one for the experience, value, and expertise. We had a lovely day experiencing all that Tuscany has to offer and would certainly recommend it to anyone who asks!”

Check availability →Read our full review

8.Private Tuscany Day Tour: Siena and Chianti Wine Region from Florence

★★★★★★★★★★5.0 · 2 reviews

Travel from Florence with an English-speaking driver, often Marco, in a private air-conditioned minivan. See Siena’s Duomo and Piazza del Campo, then follow Chianti’s winery roads and rolling hills. Add winery visits, wine tasting, and lunch at your own cost, with hotel pickup and drop-off included.

“Marco was amazing and our tour could not have been better. He was so educational and took us to beautiful spots. We had tours 2 days in a row. One to Siena and San Gimignano with lunch at a great family owned winery. Everything was so Read more”

Check availability →Read our full review