5 Wine Country Day Trips in Italy to Build a Day Around

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.Day Tour in a Vintage Fiat 500 with Winery

★★★★★★★★★★4.4 · 41 reviews · from $146

Drive a manual vintage Fiat 500 from Siena through the Chianti Hills, with stops in Castellina in Chianti and an exclusive winery. Guides such as Lorenzo, Francesco, Gabriele, and Sam lead the small-group outing, which includes wine tasting and dry snacks. Bring a license and credit card if driving.

“Fantastic is an understatement. Gabriele was a great guide. Very knowledgeable and passionate about Tuscany and the region. Highly recommend.”

Check availability →Read our full review

4.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

5.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