
Private Day Trip: Rome to Siena & San Gimignano with Wine 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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Quick answer
Is Private Day Trip: Rome to Siena & San Gimignano with Wine Tasting worth booking?
Private Day Trip: Rome to Siena & San Gimignano with Wine Tasting is a 12-hour experience in Rome, Italy, from $284 per person. It scores 52 out of 100 on the Outty Ranking, which we label “Worth a Look”. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 52 / 100
- Rating
- Not yet rated
- Duration
- 12 hours
- From
- $284 per person
On the way from Rome to Siena, you will be fascinated by the splendid landscapes of the Tuscan hills. Sipping a good glass during the San Gimignano wine tasting will allow you to enjoy a panorama of olive groves, vineyar
What you get
- 2,5 hours guided tour in Siena
- Pick up from your location and full day car with driver at disposal.
- 2-hours wine tasting & local products in San Gimignano. Below 18 years old only non-alcoholic drinks
- drop off back to your hotel in Rome
- 1-hour in San Gimignano free time
About this experience
On the way from Rome to Siena, you will be fascinated by the splendid landscapes of the Tuscan hills. Sipping a good glass during the San Gimignano wine tasting will allow you to enjoy a panorama of olive groves, vineyards, woods, high cypresses, sunflowers, and typical stone-brick houses. A private driver will pick you up at your hotel to meet your private guide in the world-famous picturesque town of Siena. Then, you will reach the fascinating medieval San Gimignano with its peculiar towers, where you will taste one of the best wines you have ever drunk, the Chianti.
What's included
Included
- 2,5 hours guided tour in Siena
- Pick up from your location and full day car with driver at disposal.
- 2-hours wine tasting & local products in San Gimignano. Below 18 years old only non-alcoholic drinks
- drop off back to your hotel in Rome
- 1-hour in San Gimignano free time
What you'll see and do
Siena
Red-bricked Siena is an attractive UNESCO World Heritage Site and an ancient, bustling University town. It is most famous for its spectacular horse race, the “Palio.” It occurs in the enormous central square, Piazza del Campo, in summer. The landmark is the 13th-century Cathedral, built on Minerva’s sanctuary site. You will enjoy strolling and shopping through the narrow cobblestone streets.
240 minutes here
San Gimignano
WINE TASTING. Taste the Chianti and other wines accompanied by local cheese, salami, bread and olive oil. Important Note: We only allow 18 years old and above travelers to participate in the wine tasting. Minor travelers below 18 years old will be provided with non-alcoholic drinks.
240 minutes here
San Gimignano
San Gimignano has a particular allure, looking like a miniature Manhattan with famous houses and medieval defense towers. Perched at the top of a hill and surrounded by a wall, the town maintains its medieval characteristics and overlooks the Chianti Region’s fertile land. Your driver will bring you to a certified wine farm where you will appreciate the world-famous Italian wine. Grapes grow in this quiet land between the Apennines (Central Italian Mountains) and the Tyrrhenian Sea.
240 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers. Pickup begins about 720 minutes before departure.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it, fr, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 10 travelers per booking
- Operated by
- Rome Guided Visit
Know before you go
- Infants and small children can ride in a pram or stroller
- Specialized infant seats are available
- Travelers should have at least a moderate level of physical fitness
Photos






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
- $284 to $1626
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Why this scores 52
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Day Trip: Rome to Siena & San Gimignano with Wine Tasting: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Rome.
How much does Private Day Trip: Rome to Siena & San Gimignano with Wine Tasting cost?
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Prices start at $284 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 Private Day Trip: Rome to Siena & San Gimignano with Wine 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 Private Day Trip: Rome to Siena & San Gimignano with Wine Tasting worth it?
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It holds an Outty Ranking of 52 out of 100, which we label "Worth a Look". That score blends traveler sentiment (0/5 across 0 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 Private Day Trip: Rome to Siena & San Gimignano with Wine 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 Private Day Trip: Rome to Siena & San Gimignano with Wine 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 Private Day Trip: Rome to Siena & San Gimignano with Wine Tasting?
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Around 0 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 Private Day Trip: Rome to Siena & San Gimignano with Wine 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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