Private Tour: Guided Hike in Tuscany with Transport from Siena
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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
5.0/5
Based on 6 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Tour: Guided Hike in Tuscany with Transport from Siena worth booking?
Private Tour: Guided Hike in Tuscany with Transport from Siena is a 7-hour experience in Siena, Italy, from $190 per person. It scores 64 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 6 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 64 / 100
- Rating
- 5/5 (6)
- Duration
- 7 hours
- From
- $190 per person
Explore Tuscany's picturesque rolling hills on a private, full-day hiking and sight-seeing tour with transport from Siena. Enjoy a scenic, full-day adventure with your expert guide with a half-day hike through the beauti
What you get
- Hotel pickup and drop-off
- Transport by air-conditioned minivan (maximum 8 passengers)
- Private guide
- Round-trip transportation from Siena to San Gimignano
- Farm lunch with wine
About this experience
Explore Tuscany's picturesque rolling hills on a private, full-day hiking and sight-seeing tour with transport from Siena. Enjoy a scenic, full-day adventure with your expert guide with a half-day hike through the beautiful rolling hills of Tuscany, between forests, olive groves and vineyards before visiting a local farm for lunch with wine. In the afternoon, visit the medieval hilltop town of San Gimignano for a walk around its UNESCO World Heritage-listed city center. Spend time at your leisure browsing the main sights and boutique stores of local crafts and products before the final, return drive to Siena.
What's included
Included
- Hotel pickup and drop-off
- Transport by air-conditioned minivan (maximum 8 passengers)
- Private guide
- Round-trip transportation from Siena to San Gimignano
- Farm lunch with wine
Not included
- Gratuities
What you'll see and do
Piazza del Duomo
Visit the main piazza's of town and try the wolrd champion gelato (not included)
60 minutes here
Historic Centre of San Gimignano
Visit the UNESCO world heritage centre of San Gimimgnano
60 minutes here
Where it starts and ends
Meeting point
Siena
From under the large tree in front of the church in Piazza San Domenico
Hotel pickup
Pickup is available for selected locations. Pickup begins about 5 minutes before departure.
Ends at
From under the large tree in front of the church in Piazza San Domenico
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 9 travelers per booking
- Operated by
- Tuscan Escapes by Papilio SRL
Know before you go
- Not recommended for travelers with poor cardiovascular health
- Travelers should have at least a moderate level of physical fitness
- Suitable walking shoes required (walking/hiking boots, sneakers, closed toe shoes with non-slip soles, etc.; no flip-flops)
- Due to uneven surfaces, this tour is not recommended for those with walking difficulties, those below average fitness, young children or those using a wheelchair
Photos
What travelers are saying
Outty’s summary of the themes that recur across 6 traveler reviews. Written by us, not quoted from reviewers.
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.
Photo opportunities
3 mentionsThe views and photo stops come up again and again.
Knowledge and storytelling
2 mentionsReviewers describe the commentary as informative rather than scripted.
Physical effort
2 mentionsExpect real walking or climbing: reviewers mention the effort involved.
Traveler reviews
6 verified traveler reviews for Private Tour: Guided Hike in Tuscany with Transport from Siena. Ratings and reviews provided by Viator and Tripadvisor.
WOW! 😍 A MUST DO
WOW 😍🇮🇹🍒 🍷 a Truly wonderful day! Firstly our guide Keko was incredible he was friendly and knowledgeable. He shared so much wonderful knowledge of the area and he not only took time to answer our questions he was also interested in our own stories. Conversation flowed as we took in our surrounds. We took so much away from this experience. A little bit wiser and with bigger smiles and a bigger love for Italy. I can not recommend this experience enough. The walk was throughly enjoyable and at the end we were rewarded with beautiful wine tasting! Where the staff were also extremely friendly and informative. Thank you for such a wonderful day! This is truly a great way to spend a day in Siena 🇮🇹 Keko next time let’s walk more of the Francigena! Claire and Will - Melbourne, Australia.
via Tripadvisor
Brunello wine discoveries
We spent a fabulous day with Georgia last Friday discovering the delights of small vineyards and the beautiful wine they produce. So many highlights in the day - the wine, the Tuscan scenery, delicious lunch under the olive trees next to the vineyard, I could go on! Thanks for a memorable day!
via Tripadvisor
Our private hiking tour through...
<p>Our private hiking tour through Chianti Classico vineyards in Tuscany was everything we hoped for and more!!<br/> Silvia was an exceptional guide with tons of information about the area, the vineyards and the city of Siena, especially loved her recommendation for dinner!!<br/> The hike is a bit more strenuous than we expected but Silvia was very patient and we went at a comfortable pace... The scenery was beyond spectacular and lunch was Amazing!! Especially the Chianti!! <br/> Unfortunately we had a downpour during our time in San Gimignano but we still enjoyed the town.<br/> Highly recommend Tuscan Escapes!!!</p>
via Viator
This was quite simply a wonderful...
<p>This was quite simply a wonderful day in the Tuscan countryside. We stayed in Siena for a number of nights but wanted to see the picture postcard landscape which is associated worldwide with Tuscany and we did just that. This trip gets you out among the vineyard and olive groves so you really experience the colours of Tuscany. There is really no one else about but you, your guide and every on often you come across someone working among the vines. The terracotta rooftops, the citrus trees and of course the poppies all help to leave you with images of Tuscany you will never forget. Our Guide Silivia was great and very attentive. She prepared a wonderful picnic after our walk which was a wonderful way to finish the day. Book this trip. I've read all the descriptions of the other trips on offer around the Siena area but this one is something different and does not disappoint.</p>
via Viator
We had a great day with Jacopo. He...
<p>We had a great day with Jacopo. He tailored the hike to what we were interested in doing. Milo showed up with a great picnic lunch. Very enjoyable!</p>
via Viator
Good to know
- Duration
- 7 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $190 to $600
- Hotel pickup
- Available for selected locations
- 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.
Private Tour: Guided Hike in Tuscany with Transport from Siena: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Siena.
How much does Private Tour: Guided Hike in Tuscany with Transport from Siena cost?
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Prices start at $190 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Siena usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Tour: Guided Hike in Tuscany with Transport from Siena take?
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Plan for about 7 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 Siena is not rushed.
Is Private Tour: Guided Hike in Tuscany with Transport from Siena 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 (5/5 across 6 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Siena, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Tour: Guided Hike in Tuscany with Transport from Siena?
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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 Tour: Guided Hike in Tuscany with Transport from Siena suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 7-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Tour: Guided Hike in Tuscany with Transport from Siena?
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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 Siena 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 Siena and add a light layer if any part of the 7-hour experience runs outdoors or after sunset.
Where does Private Tour: Guided Hike in Tuscany with Transport from Siena 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 Siena 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 Siena?
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On Outty we rank every Siena experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena, Skip the Line: Siena Duomo and City Walking Tour, Siena: A Wine Tour and Tasting Experience. 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 Siena?
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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 Siena?
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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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