Tuscany Hiking Tour from Siena Including Wine Tasting
Siena, Italy

Tuscany Hiking Tour from Siena Including Wine Tasting

Outty Ranking 86 4.9 · 125 traveler reviews4 hoursFrom $69
Instant mobile ticketSpots available today

Outty Ranking

86/100

Exceptional. Our proprietary evaluation. How we score

Traveler rating

4.9/5

Based on 125 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 $69 per person. It scores 86 out of 100 on the Outty Ranking, which we label “Exceptional”, based on a 4.9/5 rating across 125 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 (125)
Duration
4 hours
From
$69 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 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 you get

    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 fortress, Tuscany Hiking Tour from Siena Including Wine TastingGuided Hike in Tuscany, Tuscany Hiking Tour from Siena Including Wine TastingTuscan countryside, Tuscany Hiking Tour from Siena Including Wine TastingSavour local wine as a prize at the end of the hike, Tuscany Hiking Tour from Siena Including Wine TastingTuscany Hiking Tour from Siena Including Wine Tasting, photo 6Tuscany Hiking Tour from Siena Including Wine Tasting, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 125 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    8 mentions

    Travelers single out the guide as the reason the experience works.

    Knowledge and storytelling

    8 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Food and drink

    4 mentions

    The tastings and food stops are a highlight for most reviewers.

    Physical effort

    4 mentions

    Expect real walking or climbing: reviewers mention the effort involved.

    Photo opportunities

    2 mentions

    The views and photo stops come up again and again.

    Traveler reviews

    125 verified traveler reviews for Tuscany Hiking Tour from Siena Including Wine Tasting. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    114
    4 star
    9
    3 star
    2
    2 star
    0
    1 star
    0
    Sort
    Sandra_J · October 2026

    This was an outstanding...

    This was an outstanding experience. The guide, Giovanni, is also a naturalist, and in the way he explained different plants and other things we were seeing. He was friendly, witty, and very knowledgeable. The map we were given for the bus back to Siena was confusing, but he helped several of us locate the bus stop.

    via Viator

    Jill_M · October 2026

    Lovely walk with Giovanni

    Nice easy walk with Giovanni with lots of information about plants, trees and history of the area. Beautiful weather and lovely views.

    via Viator

    dat111 · October 2026

    Not as Expected but Great Tour

    our pick up was confusing and the pick up person was not friendly. The tour did not meet the description HOWEVER, our guide, Giavanni. was amazing.

    via Tripadvisor

    Wendy_H · June 2026

    Easy walk with nature guide

    Easy 8km walk from La Ville to Monteriggioni. Well paced walk. Guide was a nature guide and could point out animals, trees and fruit along the way.

    via Viator

    Kate_M · June 2026

    Beautiful hike with very...

    Beautiful hike with very knowledgeable guide on the Via Francigena, up to Monterregioni for a lovely wine tasting. Hike was longer than I thought based on Viator description; but guide was great and very flexible.

    via Viator

    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
    44
    Verdict
    Exceptional

    Who runs this experience

    Operated by Tuscan Escapes by Papilio SRL, who run 14 experiences we rank across 1 city, with an average Outty Ranking of 72.9 and 2 in the 90+ Club.

    See everything Tuscan Escapes by Papilio SRL runs

    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)82
    Booking momentum (14% weight)79
    Value for money (12% weight)100
    Listing quality (10% weight)75
    Local standing (8% weight)66
    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?

    +

    Prices start at $69 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?

    +

    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?

    +

    It holds an Outty Ranking of 86 out of 100, which we label "Exceptional". That score blends traveler sentiment (4.9/5 across 125 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most highly reviewed in Siena, and how flexible the cancellation terms are.

    Can I cancel or reschedule Tuscany Hiking Tour from Siena Including Wine Tasting?

    +

    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?

    +

    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?

    +

    Around 44 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?

    +

    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?

    +

    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?

    +

    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, Siena: A Wine Tour and Tasting Experience, Small-Group Montepulciano and Pienza Day Trip from Siena. 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?

    +

    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?

    +

    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?

    +

    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 Tuscany Hiking Tour from Siena Including Wine Tasting?

    +

    Included: Wine samples; Transport by air-conditioned minivan; and Guide. Not included: Hotel pickup and drop-off; Gratuities; and Food and drinks (unless specified). Always check the voucher for the final list before you travel.

    Where is the meeting point for Tuscany Hiking Tour from Siena Including Wine Tasting?

    +

    Starting point is from outside the pharmacy next to the train stations main entrance. Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.

    What languages is Tuscany Hiking Tour from Siena Including Wine Tasting offered in?

    +

    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 Tuscany Hiking Tour from Siena Including Wine Tasting?

    +

    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 Tuscany Hiking Tour from Siena Including Wine Tasting wheelchair or stroller accessible?

    +

    The operator notes: Not recommended for pregnant travelers. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.

    What happens to Tuscany Hiking Tour from Siena Including Wine Tasting if the weather is bad?

    +

    This experience depends on good weather. If it is canceled because of poor weather, you are offered a different date or a full refund.

    What do travelers say about Tuscany Hiking Tour from Siena Including Wine Tasting?

    +

    Across 125 reviews averaging 4.9 out of 5, recurring themes include the guide, knowledge and storytelling, food and drink. Travelers single out the guide as the reason the experience works. One thing to know: Expect real walking or climbing: reviewers mention the effort involved.

    Ready to lock in your spot?

    Pick a date, choose your group, and see the exact price for Tuscany Hiking Tour from Siena Including Wine Tasting.

    Pick your date