Tuscany Hiking Tour from Siena Including Wine Tasting in Siena
Siena, Italy

Tuscany Hiking Tour from Siena Including Wine Tasting

Outty Ranking 86 4.9 · 122 traveler reviews4 hoursFrom $60

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September 2026

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Adults

Age 13 and over

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Age 12 and under

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Outty Ranking

86/100

Exceptional. Our proprietary evaluation. How we score

Traveler rating

4.9/5

Based on 122 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Tuscany Hiking Tour from Siena Including Wine Tasting worth booking?

Tuscany Hiking Tour from Siena Including Wine Tasting is a 4-hour experience in Siena, Italy, from $60 per person. It scores 86 out of 100 on the Outty Ranking, which we label “Exceptional, based on a 4.9/5 rating across 122 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
86 / 100
Rating
4.9/5 (122)
Duration
4 hours
From
$60 per person

Leave Siena behind and hike part of Via Francigena, an ancient pilgrimage route through rural Tuscany, followed by a wine tasting in the village of Monteriggioni. Embark on a 5-mile (8-km) trek that passes through the he

What you get

  • Wine samples
  • Transport by air-conditioned minivan
  • Guide

About this experience

Leave Siena behind and hike part of Via Francigena, an ancient pilgrimage route through rural Tuscany, followed by a wine tasting in the village of Monteriggioni. Embark on a 5-mile (8-km) trek that passes through the heart of the Tuscan countryside, past picturesque castles, villages, vineyards and ruins. Once you reach the medieval walled village of Monteriggioni, reward yourself during a wine tasting session, where you will sip on 3-4 different local, organic wines. Return to Siena at your own leisure by bus (bus tickets provided).

What's included

Included

  • Wine samples
  • Transport by air-conditioned minivan
  • Guide

Not included

  • Hotel pickup and drop-off
  • Gratuities
  • Food and drinks (unless specified)

Where it starts and ends

Meeting point

Siena

Starting point is from outside the pharmacy next to the train stations main entrance.

Hotel pickup

No pickup: everyone meets at the start point.

Ends at

Starting point is from outside the pharmacy next to the train stations main entrance.

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
Mon, Thu
Group size
Up to 8 travelers per booking
Operated by
Tuscan Escapes by Papilio SRL

Know before you go

  • Service animals allowed
  • Public transportation options are available nearby
  • Not recommended for pregnant travelers
  • Not recommended for travelers with poor cardiovascular health
  • Travelers should have at least a moderate level of physical fitness
  • Not recommended for people with physical disabilities or unable to walk on uneven ground and countryside footpaths for 3 hours
  • Comfortable shoes are recommended

Photos

Monteriggioni fortressGuided Hike in TuscanyTuscan countrysideSavour local wine as a prize at the end of the hikeTuscany Hiking Tour from Siena Including Wine Tasting in Siena, photo 6Tuscany Hiking Tour from Siena Including Wine Tasting in Siena, photo 7

Good to know

Duration
4 hours
Free cancellation
Up to 24h before
Minimum age to book
All ages
Availability
Bookable today
Runs on
Mon, Thu
Hotel pickup
No pickup, meet at start point
Booked in 30 days
43
Verdict
Exceptional

Why this scores 86

The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

Traveler sentiment (30% weight)91
Review evidence (18% weight)80
Booking momentum (14% weight)76
Value for money (12% weight)93
Listing quality (10% weight)90
Local standing (8% weight)65
Booking flexibility (8% weight)100

Tuscany Hiking Tour from Siena Including Wine Tasting: questions travelers ask

Practical detail on this experience, plus the wider planning questions for Siena.

How much does Tuscany Hiking Tour from Siena Including Wine Tasting cost?

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Prices start at $60 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 Tuscany Hiking Tour from Siena Including Wine Tasting take?

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Plan for about 4 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 Tuscany Hiking Tour from Siena Including Wine Tasting worth it?

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It holds an Outty Ranking of 86 out of 100, which we label "Exceptional". That score blends traveler sentiment (4.9/5 across 122 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Siena, and how flexible the cancellation terms are.

Can I cancel or reschedule Tuscany Hiking Tour from Siena Including 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 Tuscany Hiking Tour from Siena Including Wine Tasting suitable for kids and families?

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Yes, all ages are welcome. Families should still weigh the 4-hour running time, and strollers are easier on the earlier, quieter departures.

How far in advance should I book Tuscany Hiking Tour from Siena Including Wine Tasting?

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Around 43 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 4-hour experience runs outdoors or after sunset.

Where does Tuscany Hiking Tour from Siena Including 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 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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