
San Gimignano and Siena Private Wine Tasting Tour with Lunch
Traveler rating
5.0/5
Based on 4 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is San Gimignano and Siena Private Wine Tasting Tour with Lunch worth booking?
San Gimignano and Siena Private Wine Tasting Tour with Lunch is a 9-hour experience in Lucca, Italy, from $474 per person. It scores 61 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 4 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 61 / 100
- Rating
- 5/5 (4)
- Duration
- 9 hours
- From
- $474 per person
This tour includes a car at your disposal during the tour and a transfer to San Gimignano, where you’ll have free time to explore the beautiful medieval village of San Gimignano. Then transfer to a winery in the countryside where you’ll have a guided tour of the estate, a winery lunch in the cellar with local products (Lasagna or Tuscan Ribollita + Roasted meat with roasted potatoes and vegetables + Dessert with Cantuccini and Vinsanto) and a Wine & Olive Oil Tasting of 8 wines and oils with Appetizers (Tuscan cheeses and salami, Bruschetta and snack). After Lunch, 2 hrs free tour of Siena: its soaring skyline is its pride, dominated by the gothic cathedral (Duomo is one of the most spectacular in Italy and one of the few to have been built south of the Alps in full Gothic style) and the taut needle of the Torre del Mangia and yet the shell-shaped Piazza del Campo, probably captures the most attention and fame.
What you get
About this experience
This tour includes a car at your disposal during the tour and a transfer to San Gimignano, where you’ll have free time to explore the beautiful medieval village of San Gimignano. Then transfer to a winery in the countryside where you’ll have a guided tour of the estate, a winery lunch in the cellar with local products (Lasagna or Tuscan Ribollita + Roasted meat with roasted potatoes and vegetables + Dessert with Cantuccini and Vinsanto) and a Wine & Olive Oil Tasting of 8 wines and oils with Appetizers (Tuscan cheeses and salami, Bruschetta and snack). After Lunch, 2 hrs free tour of Siena: its soaring skyline is its pride, dominated by the gothic cathedral (Duomo is one of the most spectacular in Italy and one of the few to have been built south of the Alps in full Gothic style) and the taut needle of the Torre del Mangia and yet the shell-shaped Piazza del Campo, probably captures the most attention and fame.
What's included
Included
- Private transportation
- On-board WiFi
- Lunch with wine tasting
- In-vehicle air conditioning
- 2 hr free time in Siena
- 1 hr free time in San Gimignano
Not included
- Gratuities
What you'll see and do
Lucca
Pick up at your accommodation and transfer to San Gimignano.
90 minutes here
San Gimignano
First stop in San Gimignano, where you’ll have free time to explore the beautiful medieval village of San Gimignano.
60 minutes here
Ulignano
Transfer to a winery in the countryside where you’ll have a guided tour of the estate, a winery lunch in the cellar with local products (Lasagna or Tuscan Ribollita + Roasted meat with roasted potatoes and vegetables + Dessert with Cantuccini and Vinsanto) and Wine & Olive Oil Tasting of 8 wines and oils with Appetizers (Tuscan cheeses and salami, Bruschetta and snack).
135 minutes here
Siena
Transfer and 2-hrs free walking tour of Siena: its soaring skyline is its pride, dominated by the gothic cathedral (Duomo is one of the most spectacular in Italy and one of the few to have been built south of the Alps in full gothic style) and the taut needle of the Torre del Mangia and yet the shell-shaped Piazza del Campo, probably captures the most attention and fame.
150 minutes here
Lucca
Transfer back from Siena to your accommodation.
105 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers. Pickup begins about 5 minutes before departure.
Options you can book
From Florence
Pick up/Drop off in Florence Pickup included
San Gimignano and Siena Private Wine Tasting Tour with Lunch
Pickup included
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- Road Trippin' Italy
Know before you go
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- 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 4 traveler reviews. Written by us, not quoted from reviewers.
Food and drink
3 mentionsThe tastings and food stops are a highlight for most reviewers.
The guide
2 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
2 mentionsReviewers describe the commentary as informative rather than scripted.
Organization
1 mentionPickup, timing, and logistics are described as running smoothly.
Good for families
1 mentionReviewers traveling with kids report it landed well with their group.
Physical effort
1 mentionExpect real walking or climbing: reviewers mention the effort involved.
Traveler reviews
4 verified traveler reviews for San Gimignano and Siena Private Wine Tasting Tour with Lunch. Ratings and reviews provided by Viator and Tripadvisor.
Excellent tour! San...
Excellent tour! San Gimignano and Siena are both pretty far from Lucca so we'd given up on seeing them on this trip until we saw this tour. It was amazing to get to go to both and the wine tasting on top made it even better than we'd hoped. We are traveling with our dog and were worried this would be an issue, but they were super accommodating and even booked us a bigger vehicle so that we'd have plenty of space during the drive. Benedetta was very helpful and prompt in every communication and our driver Biagio was super friendly and informative throughout the trip. My only complaint is that I wish it could've lasted longer. We would've loved another hour or two in Siena. But I guess this means we'll just have to come back again.
Response from the operator: Thank you so much for taking the time to share such a thoughtful review! We’re thrilled to hear that the tour exceeded your expectations and that you enjoyed discovering San Gimignano, Siena, and our wine tasting experience. As for wishing you had more time in Siena… we think that’s the perfect reason to come back! We’ll be looking forward to welcoming you to Italy again. 🇮🇹🍷🐾
via Viator
Sensational San Gimignano and Siena tour
From the moment I book this tour Benedetta was incredible! Our driver Biagio was absolutely amazing. San Gimignano and Siena are such captivating places to visit. Our lunch was above and beyond in quantity and quality. I can’t recommend this tour enough.
Response from the operator: Thank you! 💜
via Tripadvisor
Lucca 2024
Benadetta was amazing in coordinating several transfers and tours for us while our stay in Lucca. The company was professional, on time and very courteous. Would definitely use again when back in Lucca.
Response from the operator: Thank you April! See you next time!! ;)
via Tripadvisor
Trip of a Lifetime
This company is the epitome of professionalism, ease and luxury. We stayed in a villa outside of Lucca during a beautiful week in February. Our extended family of 12 ranged in age from 13-78. This trip of a lifetime could not have been possible without the transfers and tours provided by Benedetta. I began contacting Benedetta six months prior to our trip. Every email I sent was responded to promptly and thoroughly. She arranged private transfers from our villa to the train, Florence and Rome. We took two tours. One was a day tour to Florence that was enjoyed by all. Our favorite tour was to San Gimignano, wine tasting and Siena. It was the highlight of our trip. I commend the safety, knowledge and professionalism of all the drivers we had throughout the week. Our villa was at the top of a very steep mountain. Accessing this beautiful home was quite difficult. Thankfully, we felt safe with our drivers. I honestly don’t know what we would have done without them. A special “Grazie Mille” to Benedetta, Riccardo and Biaggio. You are wonderful people who showed us the beauty of your country. We are grateful to all of you for making this a trip of a lifetime! Everything was “so beautiful!”
Response from the operator: Thank you! I hope to see you again in Tuscany!
via Tripadvisor
Good to know
- Duration
- 9 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 1
- Verdict
- Solid Choice
Who runs this experience
Operated by Road Trippin' Italy, who run 6 experiences we rank across 3 cities, with an average Outty Ranking of 51.6.
See everything Road Trippin' Italy runsWhy this scores 61
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
San Gimignano and Siena Private Wine Tasting Tour with Lunch: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Lucca.
How much does San Gimignano and Siena Private Wine Tasting Tour with Lunch cost?
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Prices start at $474 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Lucca usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does San Gimignano and Siena Private Wine Tasting Tour with Lunch take?
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Plan for about 9 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 Lucca is not rushed.
Is San Gimignano and Siena Private Wine Tasting Tour with Lunch worth it?
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It holds an Outty Ranking of 61 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 4 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Lucca, and how flexible the cancellation terms are.
Can I cancel or reschedule San Gimignano and Siena Private Wine Tasting Tour with Lunch?
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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 San Gimignano and Siena Private Wine Tasting Tour with Lunch suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 9-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book San Gimignano and Siena Private Wine Tasting Tour with Lunch?
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Around 1 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 Lucca 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 Lucca and add a light layer if any part of the 9-hour experience runs outdoors or after sunset.
Where does San Gimignano and Siena Private Wine Tasting Tour with Lunch 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 Lucca 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 Lucca?
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On Outty we rank every Lucca experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Tuscan Wine Tour in Lucca by van, Lucca’s Ultimate Food Tour: Full Tuscan Meal by Do Eat Better, Lucca Bikes and Bites with food tastings for Small Groups or Private. 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 Lucca?
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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 Lucca?
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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.
What is included in San Gimignano and Siena Private Wine Tasting Tour with Lunch?
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Included: Private transportation; On-board WiFi; Lunch with wine tasting; In-vehicle air conditioning; and 2 hr free time in Siena. Not included: Gratuities. Always check the voucher for the final list before you travel.
Does San Gimignano and Siena Private Wine Tasting Tour with Lunch include hotel pickup?
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Yes, pickup is offered for every traveler from 21 listed pickup locations in and around Lucca. Be ready about 5 minutes before the start time.
What languages is San Gimignano and Siena Private Wine Tasting Tour with Lunch offered in?
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It runs in English. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for San Gimignano and Siena Private Wine Tasting Tour with Lunch?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
Is San Gimignano and Siena Private Wine Tasting Tour with Lunch wheelchair or stroller accessible?
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The operator notes: Infants and small children can ride in a pram or stroller; and Specialized infant seats are available. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to San Gimignano and Siena Private Wine Tasting Tour with Lunch if the weather is bad?
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It generally runs rain or shine, so dress for the forecast in Lucca. Standard cancellation terms apply: free cancellation up to 24 hours before the start.
What do travelers say about San Gimignano and Siena Private Wine Tasting Tour with Lunch?
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Across 4 reviews averaging 5.0 out of 5, recurring themes include food and drink, the guide, knowledge and storytelling. The tastings and food stops are a highlight for most reviewers. One thing to know: Expect real walking or climbing: reviewers mention the effort involved.
What booking options are available for San Gimignano and Siena Private Wine Tasting Tour with Lunch?
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There are 2 options to choose from, including From Florence, San Gimignano and Siena Private Wine Tasting Tour with Lunch. Prices and start times differ by option, so compare them on the booking screen.
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