Day Trips in Tuscany — 15 That Justify the Detour

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

From Florence, spend a full day touring Siena, San Gimignano, Pisa, and the Chianti countryside by air-conditioned coach. Walk through Siena with a local guide, enter its striking cathedral, enjoy a farmhouse lunch and four-wine tasting at Fattoria Poggio Alloro, then explore two medieval towns and Pisa’s Square of Miracles. Tower tickets require an upgrade.

“Davide was amazing and so knowledgeable. We had a wonderful experience and laughed a lot! We would recommend to anyone”

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2.Pisa, Siena and San Gimignano Day Trip with Lunch

★★★★★★★★★★4.6 · 9,771 reviews · 12 - 12.5 hours · from $58Best value

Spend 12 to 12.5 hours exploring Tuscany by coach, with stops in Pisa, Siena, San Gimignano, and a Chianti winery. You get free time at the Leaning Tower and medieval hill town, plus a Tuscan meal and wine tasting. Siena’s guided walk and cathedral entry are available only in English.

“It was a long day, but worth it. it was very well organised, nice lunch, enough time at each stop. The tour operators gave us a great history background of each destination. I would definitely recommend this tour.”

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3.Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

★★★★★★★★★★4.5 · 6,006 reviews · 12 hours (approx.) · from $78

Spend about 12 hours touring Tuscany from Florence, with guided Siena, free time in San Gimignano and Pisa, and an optional winery lunch with wine pairing. Guides such as Constantino, Sara, Jacopo, and Sebastiano have earned praise for keeping the large group informed and on schedule. Expect plenty of walking and limited time at each stop.

“You get a great overview of many places in a single day. There is not a lot of time for in depth sightseeing but you get to many places. They pull it off flawlessly.”

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4.Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 5,232 reviews · 12 hours (approx.) · from $83

Spend about 12 hours traveling from Rome to Tuscany by air-conditioned coach. Walk through Montepulciano, visit San Biagio, eat a three-course farm lunch with regional wines, and enjoy free time in UNESCO-listed Pienza. Guides such as Anna, Barbara, Antonino, and Flavio are known for adding useful history and Rome tips along the way.

“Our tour guide Barbara was very entertaining and informative. We enjoyed the views. Our favorite stop was Montepulciano. It is a long day but we are glad we did it.”

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5.San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 4,432 reviews · 11 hours (approx.) · from $83

Leave Florence by coach for San Gimignano’s towers, Monteriggioni’s fortress walls, and Siena’s Gothic center. At a Chianti winery, taste three Tuscan wines with a three-course lunch. Choose the Siena walking tour and cathedral entry if you want more guided history. Expect hills, uneven streets, and a long day.

“Sandro was great as our guide for all our destinations today! Highly recommend and lucky to get him!”

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6.Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

★★★★★★★★★★5.0 · 2,283 reviews · 12 hours (approx.) · from $78

From Florence, ride through Chianti to Siena, San Gimignano, and Pisa with a tour leader, local Siena guide, and optional cathedral entry. The day includes a family-run winery lunch with four wines, free time in each town, and transport by air-conditioned coach. It is efficient, social, and very full.

“Excellent, from customer service to every detail of the tour. The tour guide was professional and provided clear instructions.”

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7.Day Trip with Free Time in San Gimignano and Siena

★★★★★★★★★★4.7 · 1,624 reviews · 9 hours · from $71

Travel from Florence to San Gimignano and Siena by air-conditioned coach, with Chianti views, multilingual support, Wi-Fi, and free time in both towns. Sara, Alessandra, or another tour leader provides a short orientation and useful WhatsApp tips, while you choose your own sights, food, and walking route.

“Sarah was great and we had plenty of time to explore both towns.”

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8.Florence Day Trip: Pisa, San Gimignano and Siena with Lunch

★★★★★★★★★★4.5 · 1,108 reviews · 12 hours 15 minutes (approx.) · from $59

Start in Florence at 7:45 am for a 12-hour trip through Pisa, San Gimignano, a Chianti winery, and Siena. You get free time in Pisa and San Gimignano, an English-guided Siena walk, and an optional Tuscan lunch with wine. Guides such as Marco, Niccolò, and Alessia have earned praise for clear explanations and warm help.

“The stops around Tuscany were amazing. However, visiting Pisa was a disappointment, as it added an hour 1/2 travel time, just to take a few photos with the tower.”

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9.From Rome: Discover Florence & Pisa in a Full-Day Trip

★★★★★★★★★★4.3 · 1,090 reviews · from $84

Travel from Rome to Pisa and Florence with a bilingual tour leader, live commentary, and free time in both cities. Photograph the Leaning Tower, see Florence’s Duomo and Vecchio Bridge, and add a Florence audio guide if you wish. Guides such as Mary Jo, Aaron, Silvia, and Eliza have been praised for keeping the long day organized and friendly.

“more options for the 🚻. All the other things were good”

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10.Tuscany Day Trip: Chianti & Cooking Class Small Group

★★★★★★★★★★4.5 · 770 reviews · 11 hours 30 minutes (approx.) · from $167

Spend about 11.5 hours touring Tuscany from Florence by air-conditioned coach or minivan. Visit Castellina, Monteriggioni, San Gimignano, a Chianti wine estate, and Certaldo, then cook and eat a Tuscan meal at Agricola Poggio Ai Laghi. Guides such as Marco, Marta, and Emma have earned warm praise, but expect a long, walking-heavy day.

“Wonderful day. Siena tour guide was pleasant. I would suggest skipping the pre fixed lunch, food was just ok and took too much time from the visit. Also Lorenzo winery was beautiful with stunning views but the tasting was just ok.”

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11.Siena & San Gimignano Day Trip with Lunch & Wine

★★★★★★★★★★4.6 · 426 reviews · from $84

Travel from Florence to Siena and San Gimignano by air-conditioned coach, with guides such as Renata, Nathan, and Ornella sharing local stories along the way. You’ll get a guided Siena visit, free time in both towns, a three-course winery lunch, and four Tuscan wines in the Chianti countryside.

“We enjoyed all historical information & facts that our guide Renata shares with us. She was a delightful guide the entire day!”

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12.Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence

★★★★★★★★★★5.0 · 405 reviews · 8 hours (approx.)

Travel from Florence by private car or minivan to Siena, San Gimignano, and the Chianti hills. Your English-speaking driver, often Marco, Simone, Massimo, or Samuele, handles the roads and shares local stories. Add a winery lunch and tasting for €50 to €70 per adult, but expect less time in the towns.

“This was our favorite highlight of the trip. We have traveled quite a lot and can hands down say Marco is the best guide anyone could have. We learned a lot of interesting facts about his country. The winery lunch and visit was so relaxing and enjoyable. Wonderful day all the way around”

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13.Pisa and Lucca Day Trip from Florence

★★★★★★★★★★4.0 · 372 reviews · 9 hours (approx.) · from $78

Travel from Florence to Pisa and Lucca by comfortable GT coach, with local walking tours available in both cities. See the Baptistery, Pisa Cathedral, Leaning Tower, Piazza dell’Anfiteatro, Lucca Cathedral, and Renaissance walls. The day includes a buccellato tasting, free time, and a return to Florence in the early evening.

“Lots of walking but worth it. It was a trip back to ancient times and the architecture was awe inspiring.”

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14.From Florence: Chianti Wine Tastings at Sunset Day Trip

★★★★★★★★★★4.7 · 274 reviews · 5 - 7 hours · from $151

Leave Florence by comfortable car or minivan for Chianti’s vineyards, hill towns, and family-run cellars. You’ll visit two estates, taste up to six wines with cheese, jam, and bruschetta, and stop for photos at Greve, Montefioralle, and Passignano Abbey. Guides such as Simone, Luigi, Alaa, and Giacomo are praised for scenic stops and local insight. Dinner is an optional add-on.

“Grazie mille to Alberto! He was an excellent, kind, professional, patient and flexible gentleman - truly unforgettable experience celebrating my milestone birthday. Highly recommended from the 'witches of Chianti' for whom the sun shone brightly on the cloudy day. Highlight was the Maurizio Brogioni winery...incredible couple, experience and products!”

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15.Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano

★★★★★★★★★★5.0 · 263 reviews · 9 hours (approx.) · from $235

Spend nine hours exploring Tuscany by luxury minivan, with free time in San Gimignano and Siena, then enjoy a vineyard tour, Chianti tasting, and seasonal lunch at a family farm. Guides such as Antonio, Elena, Sandra, and Jessica have led especially strong departures, though the schedule can feel rushed.

“As always it is the tour director and the small group that make the tour special and the sites visited come alive. Antonio did a superb job and really connected with all of us. The wine tour and lunch was a real treat. Our driver kept us on time and entertained.”

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