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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)
Spanish (Spain)
Siena, Italy

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Up to 24 hours

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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

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.

What's Included
  • 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
What's Not Included
  • Hotel pickup and drop-off
  • Gratuities
Price start from

$ 264.8

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Activity Provider: EnRoma.com

Customer Reviews

5.0
Excellent
Based on 5 reviews
J
Jane T.Google
November 13, 2025

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 M.Google
October 24, 2025

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 C.Google
October 16, 2025

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.

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 sightseeing, culture, and gastronomy. 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 . This tour includes: Round-trip transfer busFree time in towns and Chianti wine visitWine tasting and some tapasA guided tour of SienaRound-trip train ticketsFlorence-based tour leader for all Tuscany destinations. 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 preserve. Duration: 12 hours . Book your Day Trip from Rome to Tuscany by high speed train: Medieval Towns & Chianti Wine Tasting today and create memories that will last a lifetime!