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Tuscany Day Trip: Siena, San Gimignano, Wine Tasting
4.7
13 Ratings
Rome
Embark on a full-day trip from Rome to Tuscany and explore the medieval towns of Siena, San Gimignano, and Monteriggioni. Indulge in a wine tasting session in the luscious Chianti wine region. Perfect for time-limited travelers.
Embark on a full-day trip from Rome to Tuscany and explore the medieval towns of Siena, San Gimignano, and Monteriggioni. Indulge in a wine tasting session in the luscious Chianti wine region. Perfect for time-limited travelers.
Duration:
14 hours
Cancellation:
24 hours
Highlights
- Stazione Roma Termini - The day kicks off with a departure from Rome at 6:45 AM, embarking on a 1.5-hour high-speed train journey to Florence.
- Porta Romana - Upon arrival in Florence, head straight to the meeting point, a 25-minute walk from the train station. Meet the guide and begin the Tuscany adventure, departing from Florence at 8:45 AM…
- Stazione Roma Termini - The day kicks off with a departure from Rome at 6:45 AM, embarking on a 1.5-hour high-speed train journey to Florence.
- Porta Romana - Upon arrival in Florence, head straight to the meeting point, a 25-minute walk from the train station. Meet the guide and begin the Tuscany adventure, departing from Florence at 8:45 AM for a 1-hour minivan ride to the first destination.
- Monteriggioni - The initial stop is Monteriggioni, the best-preserved medieval village in Tuscany. This fortress city is a filming location for “The Gladiator” and features in “Assassin’s Creed.” Along the way, immerse in the Italian atmosphere and learn fascinating facts about Tuscany and its renowned cuisine from the tour leader.
- Siena - The second stop is the enchanting town of Siena. During the orientation walk, discover its unique architecture, pass by numerous artisan shops, and finally visit one of Italy’s most remarkable squares, Piazza del Campo, known for the famous Palio race held every July and August. Enjoy some free time to relax and explore the city at your own pace; be sure to visit the impressive Cathedral.
- San Gimignano - The next destination is San Gimignano. En route to the village, the guide will offer tips on the best spots in town. Wander through the cobblestone streets, piazzas, and palaces of this UNESCO World Heritage Site, known as the ‘Manhattan of Tuscany,’ and explore this enchanting and timeless town freely.
- Chianti Road - The tour will certainly pass through the Chianti Region, a paradise for Tuscan wine lovers. A visit to a local winery will provide an opportunity to indulge in Tuscan delights: 7 different wines, extra virgin olive oils, and balsamic vinegar will delight your taste buds, accompanied by a wonderful traditional Tuscan meal.
- Stazione Roma Termini - Conclude a truly unforgettable day by returning to Rome, arriving at approximately 8 PM.
What's Included
- Round-trip train tickets between Rome and Florence
- Transport by minivan from Florence to Tuscany - Small group experience
- 2-hour visit in Siena + Orientation walk with tour leader
- 1.5-hour visit in San Gimignano
- Quick visit to Monteriggioni
- Wine tasting in a local winery + Extra virgin olive oil tasting
- Lunch
- English-speaking tour leader
- Round-trip train tickets between Rome and Florence
- Transport by minivan from Florence to Tuscany - Small group experience
- 2-hour visit in Siena + Orientation walk with tour leader
- 1.5-hour visit in San Gimignano
- Quick visit to Monteriggioni
- Wine tasting in a local winery + Extra virgin olive oil tasting
- Lunch
- English-speaking tour leader
What's Not Included
- Gratuities
- Gratuities
Additional Information
Embark on this extensive day-journey to Tuscany from Rome. Explore the ancient communities of Siena, San Gimignano, and Monteriggioni, understand the profound history of Tuscany, and wander through the verdant region of Chianti for wine sampling. This expedition is specially curated to encapsulate the essence of Tuscany in a single day, making it ideal…
Embark on this extensive day-journey to Tuscany from Rome. Explore the ancient communities of Siena, San Gimignano, and Monteriggioni, understand the profound history of Tuscany, and wander through the verdant region of Chianti for wine sampling. This expedition is specially curated to encapsulate the essence of Tuscany in a single day, making it ideal for voyagers with limited time.
- Minimum age allowed on the tour is 18 years old
- Please note, the tour requires a minimum of 4 participants. If not reached, a private option with a supplement will be offered.
Location
Roma Termini
Via Giovanni Giolitti
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
4.7
(13 Ratings)
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Staceym_sf
Nov 27, 2025
Great tour / amazing value - Our guide Valentina was so knowledgeable about the area and history. She shared great stories and made the entire day enjoyable and fun. She made sure we knew all the best spots at each stop from gelato recommendations to places to snap the best pics. We chose this tour for the small group size and it turned out to just be our family which made it even more special and intimate. This tour definitely delivers on value - you visit three walled cities and experience a wonderful wine tasting and authentic Italian lunch in a beautiful setting. I highly recommend this tour.
Review provided by Tripadvisor
Jeanne
Nov 18, 2025
Winery and Sorrento - The wine tasting trip was great my wife and I both enjoyed visiting Sorrento and our tour guide Valentina. Thank you for the experience
Review provided by Tripadvisor
B162vxjeffb
Nov 4, 2025
Tuscany and wine tour - Lorenzo was a great guide. Saw so much of Tuscany region! Tenuta Torciano winery was spectacular!! Sienna also a must visit!
Review provided by Tripadvisor
Kennv9930jw
Oct 2, 2025
Great way to see small towns in Tuscany - Fantastic tour Guide/Driver
Great itinerary
Fabulous food at Winery
Wine tasting was average - less education and food pairing of wines than expected
Review provided by Tripadvisor
303priyamvadas
Sep 27, 2025
Amazing. - Excellent experience. Our tour guide valentina was lovely. She was very sweet and considerate. It was amazing experience.
Review provided by Tripadvisor
Pheebs_13
Mar 26, 2025
Our favourite day of our Italian trip so far! - We had a great day with Antonello! We had originally booked a different tour that couldn’t go ahead, so we ended up on a different tour which ended up being amazing. San Gimignano was our favourite stop, such a beautiful village! And the wine tasting at Torciano was one of the best we’ve had. The customer service before, after and during was also great so I wouldn’t hesitate to book another tour with this company.
Review provided by Tripadvisor
Debra_o
Jul 30, 2024
Action pack day - Action pack day well thought out and well plan trip. Train was on time out of Rome. Meeting spot was well described beautiful scenery great guide.
Review provided by Viator
Don
Jul 30, 2024
Action Packed Day - What an action pack day. Got the train in Rome as planned train was on time. Sent us a very detailed message of meeting spot in Florence scenery was beautiful a bit rush at East destination but I guess that is how we got to see you so much in oneday .
Our guide Ned very personable, knowledgeable
Review provided by Tripadvisor
Crockett06
Jul 9, 2024
Great day out - Great day out & our host was fantastic. Would highly recommend. Definitely made us think about returning to the area to explore some more.
Review provided by Tripadvisor
Ashley_r
Nov 5, 2024
Nightmare Experience - From start to finish the entire experience was the most expensive nightmare of my life. The tour we booked was cancelled and we were offered a cheaper tour that went to less locations and was much cheaper. It was advertised as a little over $100 less per person and we were told we’d be refunded the difference, but for two tickets we were only refunded $5.
Then tour day the train that was booked for us had delays, which resulted in the tour leaving without us and my husband and I spending 5+ hours on trains trying to catch up to the group which was the suggestion of the tour company. We finally joined them at the end and got to listen to how much fun the group had, and the group all paying a fraction of what we were charged. I spent the 1.5 hour van drive back to the ending point then the 1.5 hour train journey back in tears after what should have been a relaxing romantic day turned into one of the worst days of my life. I am never booking with Viator, or Italy on a budget tours again.
Review provided by Viator
