15 Tuscany Day Trips from Rome Worth Booking

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

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

Travel by air-conditioned coach from Rome into Tuscany for a guided walk in Montepulciano, lunch and wine at a local farm, a stop at San Biagio Church, and free time in UNESCO-listed Pienza. Expect a long day, steep streets, scenic views, and a group of up to 25 people.

“Thank you Anna and Pablo! We had a wonderful time in the country side. Anna was very knowledgeable and Pablo was an excellent driver.”

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2.From Rome to Tuscany: Discover Florence and Pisa in One Day

★★★★★★★★★★4.5 · 804 reviews · 14 hours (approx.) · from $180

This 14-hour Amigo Tours trip takes you by air-conditioned bus from Rome to Pisa and Florence. Expect bilingual guidance, free time at major sights, optional Florence audio, and a long day with about four hours on the road each way.

“It was a nice trip. Our guide Titsiano was very friendly, helpful and cooperative. Great experience.”

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3.Tuscany Comfort Day Tour from Rome with Wine & Lunch

★★★★★★★★★★5.0 · 313 reviews · 12 hours (approx.) · from $349Top rated

Travel from Rome to Florence by prebooked high-speed train, tour Florence with an English-speaking guide, then ride by private van to a family-run winery near San Gimignano for vineyard views, wine, and a light lunch. Guides may include Antonio, Sara, or Jessica.

“Today was amazing! We were met at the train station by a rep from Italia iShe walked us right to the platform and gave us specific instructions. When we arrived in Florence, Antonio was waiting for us for our walking tour. He was fantastic! He was full of knowledge and friendly! We later took two vans with him to the winery., What a fabulous experience! Andrea gave us a tour of his beautiful winery! Breathtaking views! We ate delicious cheeses, balsamic, pasta, gelato, and fantastic wine! Highly recommend this tour!! We had the best day!”

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4.5-Day Best of Italy: Assisi, Siena, Florence, Venice and more

★★★★★★★★★★4.5 · 285 reviews · 5 days (approx.) · from $1,031

Travel from Rome through Assisi, Siena, Florence, Bologna, Venice and Montepulciano in five busy days. You get four-star hotels, guided walks, meals, attraction tickets and a deluxe coach. Guides such as Clara, Nicky, Sabrina and Stefano have earned praise for keeping this large group organized and well cared for.

“This was such an amazing trip! Would highly recommend for those wanting to explore as much in a short time.”

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5.Florence & Tuscany Day Tour by High-Speed Train

★★★★★★★★★★4.6 · 126 reviews · from $231

Travel from Rome to Florence in 85 minutes, then follow an English-speaking guide such as Antonio or Jessica through Renaissance landmarks. Afterward, enjoy a family-run winery tasting with local food and a light lunch, then explore San Gimignano before returning to Rome.

“We had a lovely day in Florence...3hr walking tour followed by free-time exploring the city for ourselves. Antonio was an excellent guide...knowledgeable & amenable. There was a slight issue with occasional interference on the headsets but it didn't significantly detract from our tour. An excellent day out!”

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6.Tuscany Full-Day Guided Trip w/Wine Tasting

★★★★★★★★★★4.5 · 69 reviews · from $243

Spend eight hours with an English-speaking driver in a small group of up to eight, visiting Montemerano, Saturnia’s thermal waterfall, and cliff-top Pitigliano. You’ll also taste Tuscan wines with local food at a winery such as Villa Acquaviva. Guides including Mirko and Sandro have earned strong praise for their personal approach.

“Our guide, Sandro, was the key to our fabulous day. He was charming and gave us amusing and informative insights into Italy and its people with his anecdotes. We loved both Montemerano and Pitigliano, especially because there were so few people (which is exactly what we were looking for). The Acquavit Winery was equally beautiful and uncrowded, and we enjoyed just strolling the beautiful grounds drinking wine and petting the winery cat. Every other day we spent in Italy felt rushed and a little chaotic. This entire day was peaceful, and much of that was due to Sandro's friendly, patient and kind demeanor.Read more”

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7.Tuscany, Montepulciano Tour with Wine & Lunch

★★★★★★★★★★4.9 · 36 reviews · from $137

Travel from Rome to Montepulciano and Montalcino by air-conditioned coach, with Wi-Fi, a bilingual guide, DOCG wine tastings, and lunch in an ancient friars’ refectory. You’ll see a 13th-century winery, an Etruscan tomb, Twilight filming sites, and Tuscany’s famous hill towns.

“The tour was well organized, with every part of the itinerary running smoothly. The wine and food were outstanding, capturing the authentic flavors of Tuscany. Both the guide and driver were fantastic, adding personal insights and ensuring the entire experience was enjoyable and memorable.”

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8.Private Day-Tour of Tuscany

★★★★★★★★★★4.3 · 23 reviews · from $190

Leave Rome for a private 10-hour day in Tuscany with an English-speaking driver. Visit Montepulciano’s underground wine cellars, taste local wine, stroll through Renaissance Pienza, and shop for pecorino cheese. Gina and Marou are among the guides named in guest feedback.

“Very kind guide with excellent recommendations— thank you Gina”

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9.Taste of Tuscany: Food & Wine tour with Florentine Cuisine

★★★★★★★★★★4.9 · 19 reviews · from $78Best value

Walk Florence’s historic center from Piazza della Passera toward Santa Croce, stopping at family-run eateries for schiacciata, pappardelle with wild-boar ragù, local specialties, gelato, and Chianti. English-speaking guides such as Erica, Ryana, and Sam have been praised for warm, engaging hosting.

“Having a market tour was an amazing way to start our day in town. Gabi was our guide and she was very knowledgeable and full of energy. This was truly a great experience and i definetly recommend this !”

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10.Siena and S. Gimignano, Tuscany Wine One Day Tour

★★★★★★★★★★4.8 · 18 reviews · from $303

Spend 10 hours traveling from Rome by air-conditioned minivan to Siena, San Gimignano, and Tenuta Torciano. Your guide, possibly Monica, Luigi, Pepe, or another assigned leader, handles the day while you enjoy medieval sights, local food, and a tasting advertised as nine to ten wines.

“We originally paid for a shared tour but because nobody booked it ended up being private!! Our tour guide Monika was great and very knowledgeable, and our driver Giuseppe was great too! They made sure to stop on the ride there for coffee/breakfast since it was an early pick up. The drive was long but beautiful and worth it since public transportation to that area takes much longer. Being able to walk through Siena and San Gimignano with her giving us details/history was perfect. She was very flexible and we had time to go off on our own to explore the town as well. The wine tasting/lunch was amazing and…”

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11.Private Day-Tour of Tuscany

★★★★★★★★★★5.0 · 16 reviews · 10 hours (approx.) · from $531

Travel from Rome to Montepulciano and Pienza in a private, air-conditioned vehicle with an English-speaking driver. Taste wine in a Montepulciano cellar, sample Pecorino di Pienza, and enjoy four hours to explore two Tuscan towns at your own pace.

“Disappointing. Car & driver were fine but itinerary was very disappointing. The trip to Montepuliciano was nothing more than a visit to a wine store. We expected to go to an actual winery not a store with wine barrels. Definitely would not recommend.”

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12.Tuscany-Latium Wine Tour with Tastings

★★★★★★★★★★4.7 · 15 reviews · from $243

From Civitavecchia, join an English-speaking guide such as Mirko for a 6.5-hour small-group trip into Maremma. Visit two wineries, taste six wines with local snacks, learn about Morellino di Scansano, and enjoy Tuscan villages and vineyard views.

“We had a marvelous day! Mirko made our entire day so special. He knew all the best spots to document the trip with photo opportunities. The winery tour was intimate and top notch. For those who want to escape the hustle of the big cities and crowds this tour is nothing less than perfection!”

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13.Siena & San Gimignano Semiprivate Day Trip

★★★★★★★★★★4.2 · 9 reviews · from $451

Travel from Rome in a minivan for a full day in Tuscany. Walk San Gimignano and Siena, taste Vernaccia and Chianti with local food, and return with a driver-guide. The group has up to 14 people. Felice and Andrea are named among the standout guide and driver team members.

“Excelent private your. Both the tour guide Felice and the driver Andrea were exceptional and friendly. Great day trip from Rome. Mille Grazie!”

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14.Montepulciano and Montalcino, on the Wine Routes

★★★★★★★★★★5.0 · 8 reviews

Travel by air-conditioned coach from Rome to Montepulciano and Montalcino for guided walks, free time, a 13th-century cellar visit, DOCG wine tasting, and a Tuscan lunch. English and Spanish guides lead this 12-hour outing, which includes two glasses of wine and plenty of hill-town views.

“Absolutely loved this tour. Rolling hills, amazing wine tastings, and charming little towns. It was a perfect escape from the city. The guide was very knowledgeable, making it a truly enriching experience.”

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15.Private Tour to San Gimignano, Siena & Winery Visit

★★★★★★★★★★3.0 · 6 reviews · from $1,259

Travel by private vehicle from Rome to San Gimignano, a Chianti winery, and Siena. You’ll see Piazza della Cisterna, Piazza del Campo, and the Duomo area, then taste 15 wines and oils with Tuscan cheeses, salami, and bruschetta. The winery visit is in English.

“El proveedor Amigo tours lo cancelo el día anterior y nos cambio por otro tour a Florencia y Pisa y nadie me contesta por la devolución de la diferencia porque es mucho más economica”

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