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Day Trip from Rome to Tuscany by high speed train: Medieval Towns & Chianti Wine Tasting
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Day Trip from Rome to Tuscany by high speed train: Medieval Towns & Chianti Wine Tasting

5.0(5 reviews)
12 hour(s)
English
Skip the line
Siena, Italy

Free time to explore Monteriggioni and San Gimignano at your own pace

Visit a traditional Chianti winery for wine tasting and local tapas

Experience Tuscan culture, history, and stunning landscapes in one day

Perfect combination of sightseeing, culture, and gastronomy

Price start from

235

216.20

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Experience the natural charm and timeless beauty of Tuscany on an unforgettable tour from Florence to San Gimignano, Chianti, Siena, and Monteriggioni, complete with a delightful wine tasting. Your day begins with a scenic drive through the rolling Chianti hills, offering breathtaking views of vineyards, olive groves, and cypress-lined roads. The first stop is Monteriggioni, a beautifully preserved medieval town with its ancient walls still perfectly intact, where you can enjoy free time to explore its quaint streets, historic towers, and charming atmosphere.

Next, the tour continues to Siena, where a guided tour of the historic center awaits. Visit the exterior of the Palazzo Pubblico, admire the Torre dei Mangia, and take in the iconic Piazza del Duomo, all steeped in centuries of history and culture. After Siena, head to San Gimignano, famously known as the City of Towers and a UNESCO World Heritage Site, to marvel at its medieval towers and picturesque old town during a free visit. The tour concludes in the scenic Chianti Hills, where you will visit a traditional winery to taste Chianti red wine accompanied by local tapas, providing the perfect ending to a full day of exploration, culture, and Tuscan flavors.

Round-trip transfer bus

Free time in towns and Chianti wine visit

Wine tasting and some tapas

A guided tour of Siena

Round-trip train tickets

Florence-based tour leader for all Tuscany destinations

Hotel pickup and drop-off

Gratuities

Comfortable walking shoes

Water bottle

Travelers with Limited mobility impairments
Physically fit travelers
Nature enthusiasts
Couples
Wine lovers
Photography lovers

Wear comfortable walking shoes

Bring a water bottle to stay hydrated

Have a camera ready to capture every special moment

Confirmation will be received at time of booking

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Activity Provider: EnRoma.com

Customer Reviews

5 reviews
5.0
based on 5 reviews
J

Jane

November 13, 2025
Google

Eleanora and Martina from Italia Tours were extremely communicative from the beginning, really attentive to what we were seeking. They linked us with an accommodation service who gave recommendations for places to stay before and after the Pompei tour. The tour itself was fantastic. Our guide was an archaeologist and so passionate about her subject. The wine tasting and lunch was fabulous. The private chauffeur, Michael, who took us on to Amalfi was also wonderful and a very careful driver, so important on those narrow, windy roads. Truly a highlight of our Italy visit.

K

Kelly

October 24, 2025
Google

Nadia was simply amazing! The amount of detail and knowledge that she possesses is incredible. If you end up with her as your tour guide, you will have an amazing tour! She kept it fun, interesting, entertaining and loaded with information. The company did a great job of communicating in advance and relating changes and details. Highly recommend.

D

Danny

October 16, 2025
Google

Nadya was an incredible guide. She’s incredibly knowledgeable of the Vatican Museums and all its contents. She was not lacking in things to talk about. At one point, we were waiting in the line to the dome and it was unmoving so she went to the front and helped move the line to the dome in a manner so efficient and seemingly effortlessly, it was quite an achievement on her part. I HIGHLY recommend a tour with her. You will not be bored. Along with being knowledgeable, she’s so charismatic, kind, and funny. This was an excellent experience.

R

Robert

October 15, 2025
Google

We did a private tour with Italia Tours, and consider ourselves very fortunate that we got Nadya as our guide. She was so much fun. She’s very energetic, very knowledgeable, and she goes above and beyond to ensure you have the best experience possible. She works her network of guides and other people involved with all the sights we were at to make sure we got in as quickly as possible and stayed as long as we felt we needed to. Before we went into the Sistine Chapel, Nadya pulled out a rendering of the chapel ceiling and went over all the paintings we would be seeing. When we got inside, she secured seats for us so we could sit and study the ceiling without killing our backs and necks. The briefing on the paintings she gave us beforehand really helped make the experience of being there so much better. We understood the reasons for each painting, what they all meant. She could have just taken us in there and let us look, but she gave us knowledge that enhanced the experience. She took us to a great little restaurant for lunch. The food was excellent. She was with us from 8:30am until almost 6pm and the time seemed to fly. We were sad when the day was over. It was our first time in Rome and we feel we got the best experience we could have hoped for to see the sights we wanted to see. I can’t say enough good things about Nadya. I highly recommend if you are going to do a private tour and you want to get the best of Rome in one day, the best experience for your money, ask for Nadya!

F

Frank

September 03, 2025
Google

Did a guided small group tour with Italia Tours. Our guide Nadia was most excellent! She explained and pointed out everything providing amazing detail. If you wanted more info she would stop and give more detail. If you asked her about anything her knowledge was very impressive. I highly recommend. Worth every penny and gives a much greater connection to the individual elements of the Vatican museum.

Explore More Day Trip from Rome to Tuscany by high speed train: Medieval Towns & Chianti Wine Tasting
Explore More Day Trip from Rome to Tuscany by high speed train: Medieval Towns & Chianti Wine Tasting
Explore More Day Trip from Rome to Tuscany by high speed train: Medieval Towns & Chianti Wine Tasting
Explore More Day Trip from Rome to Tuscany by high speed train: Medieval Towns & Chianti Wine Tasting
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Day In a City

Explore More Day Trip from Rome to Tuscany by high speed train: Medieval Towns & Chianti Wine Tasting

Discover the wonders of Siena, Italy with this unforgettable experience. Experience the natural charm of Tuscany Highlights of your tour include: Free time to explore Monteriggioni and San Gimignano at your own paceVisit a traditional Chianti winery for wine tasting and local tapasExperience Tuscan culture, history, and stunning landscapes in one dayPerfect combination of sig...