From Rome: Tuscany, Siena and San Gimignano with Tasting
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.9/5
Based on 7 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is From Rome: Tuscany, Siena and San Gimignano with Tasting worth booking?
From Rome: Tuscany, Siena and San Gimignano with Tasting is a 12-hour experience in Rome, Italy, from $58 per person. It scores 64 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.9/5 rating across 7 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 64 / 100
- Rating
- 4.9/5 (7)
- Duration
- 12 hours
- From
- $58 per person
Embark on a fascinating excursion in the Tuscan hills, visiting the historic cities of Siena and San Gimignano. We will pick you up from your hotel or apartment in Rome. The tour will start with the exploration of Siena,
What you get
About this experience
Embark on a fascinating excursion in the Tuscan hills, visiting the historic cities of Siena and San Gimignano. We will pick you up from your hotel or apartment in Rome. The tour will start with the exploration of Siena, its magnificent Piazza del Campo and its majestic Duomo. Admire the medieval architecture and immerse yourself in the history and culture of this beautiful city. The tour continues to San Gimignano, known as the "Manhattan of the Middle Ages" for its imposing towers. Stroll through the cobbled streets and enjoy the panoramic views of the surrounding hills. After enjoying free time in San Gimignano we will head to a charming wine estate in the countryside where you will have the opportunity to participate in a tasting of local wines accompanied by typical products, tasting the fine Tuscan wines and discovering the secrets of their production. Return to Rome is scheduled for the afternoon.
What's included
Included
- Pick up and drop off
- Assistant for the entire duration of the tour
- Driver
- Entrance tickets to the Cathedral of Siena
- Wine and local products tasting in a historic country estate
Not included
- Gratuities
What you'll see and do
Siena
Siena, located in the heart of Tuscany, is a medieval city famous for its beauty and its historical heritage. The historic center of Siena, recognized as a World Heritage Site by UNESCO, is characterized by narrow and winding streets, historic buildings and charming squares. Piazza del Campo is the hub of city life and hosts the famous Palio, a horse race that takes place twice a year. Siena Cathedral, with its extraordinary black and white marble facade, is a masterpiece of Italian Gothic architecture. Inside, visitors can admire works of art by famous artists such as Donatello, Michelangelo and Pinturicchio. Siena is also renowned for its traditional Tuscan cuisine and fine wines, such as Chianti and Brunello di Montalcino.
120 minutes here
San Gimignano
San Gimignano, located in the heart of Tuscany, is famous for its many medieval towers, which have earned it the nickname "Manhattan of the Middle Ages". This charming city is a UNESCO World Heritage Site and offers visitors a fascinating immersion in medieval history and art. Walking through its cobbled streets, you can admire the ancient towers that stand out over the landscape. San Gimignano is also renowned for its white wine, Vernaccia di San Gimignano, one of the finest in Tuscany.
60 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers. Pickup begins about 10 minutes before departure.
Options you can book
SMALL GROUP TOUR
Tour for small groups: Small Group Tour: Accommodates a maximum of 6 people per minivan and up to 12 people per assistant Pickup included
PRIVATE TOUR
Private Tour: The private tour is wheelchair accessible. Pickup included
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- pt, en, fr, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 12 travelers per booking
- Operated by
- Mamma Mia Italia
Know before you go
- Infants and small children can ride in a pram or stroller
- Specialized infant seats are available
- Suitable for all physical fitness levels
Photos
What travelers are saying
Outty’s summary of the themes that recur across 7 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
5 mentionsReviewers describe the commentary as informative rather than scripted.
Food and drink
5 mentionsThe tastings and food stops are a highlight for most reviewers.
The guide
3 mentionsTravelers single out the guide as the reason the experience works.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
7 verified traveler reviews for From Rome: Tuscany, Siena and San Gimignano with Tasting. Ratings and reviews provided by Viator and Tripadvisor.
Wonderful educational fun Tuscany Siena Day!
Amazing from the driver Max to the toor guide Michaela & assistant Giuseppe, ALL very personable and fun =enjoyable conversation &knowledgeable loved it !=would recommend this tour -we had a great time!!!
Response from the operator: Thank you so much for your wonderful review! We’re delighted to hear that Max, Michela, and Giuseppe made your experience so enjoyable and memorable. It was a pleasure having you with us, and we hope to welcome you back soon for another fantastic adventure in Italy!
via Tripadvisor
Siena visit
Initially, we were unaware that the wine tour was actually a wine tasting. We had thought we were visiting a winery to learn about the process of winemaking, not tasting 8 different wines with a light lunch. We already know how to drink wine😊Somewhat disappointed about that. Especially with the long drive to and from. We would have like more time visiting the town Siena vs, unstructured time in churches.
via Tripadvisor
A perfect getaway from busy Rome
Exceeded expectations all around. Having a small group tour in a private van was absolutely worth paying a little more as opposed to large group tour and dealing with lots of people on a big bus. Being picked up and dropped off at hotel was also very nice not having to figure out transportation. We had our own tour guide and a driver. Tours of the city and cathedrals was educational and Dina was very knowledgeable about many different things. She was able to pivot between history, religion, and architecture intelligently. Had a little time to do some shopping in both places. The winery and staff were excellent. The wine was plenty, a great 3 course meal. The staff had us laughing off our chairs. The purchase options with discounts were good. Balsamic, several olive oils, and a few wines not sold in stores. Overall a great day spent in the Tuscany region. Highly recommended.
Response from the operator: Thank you so much for your wonderful and detailed review! We’re thrilled to hear that the private tour experience exceeded your expectations and that you enjoyed the comfort, flexibility, and personal attention provided throughout the day. We’re happy that Dina, the winery visit, and the Tuscan experiences made your journey so memorable. Your recommendation means a lot to us, and we hope to welcome you again for another amazing experience in Italy!
via Tripadvisor
Wonderful day in Tuscany
Dina and Massimo were wonderful, we were able to see and do everything that we wanted to, they were very flexible and accommodating to our group’s needs.
Response from the operator: Thank you so much for your kind review! We’re delighted to hear that you had such a wonderful experience and that our team was able to accommodate your group’s needs. We’re happy that you enjoyed your tour and had the opportunity to see and do everything you hoped for. We truly appreciate your kind words and hope to welcome you again soon for another memorable experience in Italy!
via Viator
Quiet Tuscany in January- no crowds, peaceful and so much space to fully explore without the crowds
The perfect Italian day! January is a peaceful time for Tuscan villages! Max and Paula were amazing, immediately felt welcomed and never rushed. Perfect walking tours, history, and wine.
Response from the operator: Thank you so much for this wonderful review! We are truly delighted that you experienced what you described as “the perfect Italian day.” January really does offer a special atmosphere in Tuscan villages, and knowing that you enjoyed it makes us very proud. It was a real pleasure to welcome you. We’re so happy you felt comfortable and never rushed, and that you appreciated the walking tours, the history, and of course the wine. We hope to welcome you back soon for another unforgettable experience in Tuscany!
via Tripadvisor
Good to know
- Duration
- 12 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $58 to $1104
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 2
- Verdict
- Solid Choice
Why this scores 64
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
From Rome: Tuscany, Siena and San Gimignano with Tasting: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Rome.
How much does From Rome: Tuscany, Siena and San Gimignano with Tasting cost?
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Prices start at $58 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Rome usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does From Rome: Tuscany, Siena and San Gimignano with Tasting take?
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Plan for about 12 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Rome is not rushed.
Is From Rome: Tuscany, Siena and San Gimignano with Tasting worth it?
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It holds an Outty Ranking of 64 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.9/5 across 7 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Rome, and how flexible the cancellation terms are.
Can I cancel or reschedule From Rome: Tuscany, Siena and San Gimignano with Tasting?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is From Rome: Tuscany, Siena and San Gimignano with Tasting suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 12-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book From Rome: Tuscany, Siena and San Gimignano with Tasting?
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Around 2 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Rome can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Rome and add a light layer if any part of the 12-hour experience runs outdoors or after sunset.
Where does From Rome: Tuscany, Siena and San Gimignano with Tasting start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Rome within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Rome?
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Rome runs on skip-the-line access. The Colosseum underground, the Vatican before opening, and the catacombs south of the walls all require a licensed operator, and the price gap between the good ones and the rest is smaller than you would expect. We rank by guide credentials, group size and how reliably the promised access actually materialises. On Outty we rank every Rome experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Rome Pasta and Tiramisu Class: Ravioli, Fettuccine & Fine Wine 5*, Pasta Making & Wine Tasting with Dinner in Frascati from Rome, Rome: Pizza & Tiramisu or Gelato Class with Flowing Fine Wine 5*. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Rome?
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April, May, September and October. August is hot and half the city is shut. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Rome?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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