From Rome: Day Trip to Tuscany & Siena with lunch & Wine Tasting
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From Rome: Day Trip to Tuscany & Siena with lunch & Wine Tasting

4.9(8 reviews)
14 hour(s)
English (United Kingdom)
Rome, Italy

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Explore Siena streets with stunning medieval architecture today

Discover San Gimignano towers and charming Tuscan streets

Wander historic Monteriggioni walls and picturesque Tuscan landscapes

Enjoy Chianti wine tasting through beautiful rolling hills

Discover the Iconic Medieval Towns and Rolling Hills of Tuscany on a Day Trip


Escape the historic streets of Rome for a day and immerse yourself in the breathtaking beauty of the Tuscan countryside. Your journey begins with a comfortable high-speed train ride to Florence, which serves as the gateway to the region's most famous landscapes. Once you arrive, you will join a guided tour that takes you through the heart of Tuscany, showcasing the rolling hills, cypress-lined roads, and golden vistas that have inspired artists and poets for centuries. Explopre Siena Cathedral.


The itinerary includes visits to several iconic medieval towns, including Siena and San Gimignano, where you can wander through narrow cobblestone streets and admire well-preserved architecture. You will also stop in the charming village of Monteriggioni, known for its impressive defensive walls and historical significance. Each town offers a unique glimpse into the medieval past of Italy, providing plenty of opportunities to explore local shops, historic squares, and stunning cathedrals that define the character of the region.


A highlight of the trip is a visit to the world-renowned Chianti wine region, where you will enjoy a traditional Tuscan lunch paired with local wines. At a local winery, you will learn about the viticulture practices that make Chianti wines so celebrated globally. This culinary experience allows you to savor the authentic flavors of the region, from fresh olive oils to aged cheeses, all while enjoying the peaceful atmosphere of the surrounding vineyards and olive groves.


This day trip is designed to provide a comprehensive experience of Tuscany’s most iconic sites within a single, unforgettable day. By combining efficient transportation with expert guidance, you can enjoy the best of the region without the stress of planning logistics. Whether you are interested in history, architecture, or fine wine, this excursion offers a perfect blend of culture and relaxation, ensuring you return to Rome with wonderful memories of the Italian countryside.

What's Included
  • Round-trip train tickets between Rome and Florence
  • Transport by minivan from Florence to Tuscany
  • English-speaking tour leader
  • Visit in Siena, Orientation walk with tour leader
  • Quick visit to Monteriggioni
  • Visit in San Gimignano
  • Authentic Tuscan meal
  • Traditional Ribollita Soup & Cantuccini
  • Veg, vegan and gluten free menu on request
  • Wine tasting in a local winery
  • Extra virgin olive oil tasting
What's Not Included
  • Gratuities
Price start from

$ 267.91

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Activity Provider: Authentic Italy Adventures

Customer Reviews

4.9
Excellent
Based on 8 reviews
L
Lexi A.Google
January 15, 2026

If you are in Tuscany, you MUST book a tour with Donatella and Dario. This was an absolutely amazing experience. I did a solo/private tour with Dario from Florence through Tuscany, and he was very knowledgeable. We were talking the entire time about the different wine grapes and the history of the local wineries. Every winery they chose had something special, and I was lucky enough to talk to every owner/winemaker myself to hear their story. The itinerary was carefully curated for me. We visited 4 wineries, and at every stop, it felt like I was part of the family and not just visiting a business or conducting a transaction. You can tell the wineries focus on the quality of their wine rather than the quantity, making the tasting even more special. Before the last winery, we sat down to enjoy an authentic, home-made Italian meal in a small town in the Sienna area. The food was delicious, and the people we met made it even better. The transportation was also very easy and comfortable. It was a nice Mercedes van, and Dario came into the hotel to pick me up, greet me, and help me with my bags. He then dropped me off at the train station to catch my train to Rome. This experience was fantastic, and I believe you can not get it anywhere else. I would most definitely do this again and recommend it to anyone who is in the area. Donatella and Dario will customize the experience to suit you perfectly. They build lasting relationships with these wineries and bring you in as part of their own family.

E
Eric E.Google
November 25, 2024

My wife and I had an amazing experience with Dario as our guide. He was personable, funny, and extremely knowledgeable. He took us to small family wineries that focus on quality over quantity. It was everything we had dreamed of when coming to Italy. Highly recommend.

M
mac1075 Google
October 30, 2024

We booked our reservation with Donatella having very high, hopeful, expectations. Living in Northern California wine country (Sonoma) we were looking for a more personal curated tour, not the usual large group, uninformative, rushed experience at a large corporate producer, so often the case with too many winery tours. We specifically asked to visit small, family wineries - seeking that special experience. Our reservation went smoothly, Donatella kept us up to date, confirming the when and where. The morning of our tour we were met at our hotel in Siena by Dario, right on time. Turned out we were his only clients for the day! Can’t say enough about what a friendly, funny, informative guide he was. His knowledge of the area, the history, the wines was truly top notch. Along the way we enjoyed sharing personal stories and learning a lot about his family and life beyond the tour. The wineries we visited were exactly what we hoped for - small production, family owned and operated, learning about not just the wines, but the generational family histories and wine making traditions. Each winery experience felt more like visiting an old friend, chatting over some incredible Chianti Classico. Definitely the highlight of the day, perhaps the highlight of our entire vacation in Italy, was sitting down to lunch with a private family friend in the garden of their very old Tuscan home - delicious food and wine, wonderful company. It gave us a glimpse of Tuscany life, authentic, simple, - the good life and an afternoon we will never forget (to say nothing of the homemade tiramisu!) Now home, we savor our memories for a lifetime of this incredible day with Dario, filled with great food, wine, landscapes of Tuscany, and new found friends. Donatella and Dario are exceptional in every sense of the word. We’re already looking forward to our next visit and highly recommend Wine Tour in Tuscany if you seek that specially curated, personal experience into the world of Tuscany wines. Grazie Mille, Donatella and Dario! Michael and Joanna October 2024