Chianti and Castles Tour from Siena Small Group in Siena
Siena, Italy

Chianti and Castles Tour from Siena Small Group

Outty Ranking 59 3.6 · 7 traveler reviews5 hoursFrom $43

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September 2026

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Adults

Age 13 and over

2

Children

Age 12 and under

0

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From, per person$43
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Outty Ranking

59/100

Worth a Look. Our proprietary evaluation. How we score

Traveler rating

3.6/5

Based on 7 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Chianti and Castles Tour from Siena Small Group worth booking?

Chianti and Castles Tour from Siena Small Group is a 5-hour experience in Siena, Italy, from $43 per person. It scores 59 out of 100 on the Outty Ranking, which we label “Worth a Look, based on a 3.6/5 rating across 7 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
59 / 100
Rating
3.6/5 (7)
Duration
5 hours
From
$43 per person

Discover the picturesque wine region of Chianti on a half-day excursion from Siena. Enjoy the Tuscan scenery of gently undulating hills and vineyards while tasting Chianti wines. A day journey from Siena to the Chianti

What you get

  • Visit two wineries in the Chianti area
  • Expert multilingual guides
  • Wine, oil and balsamic vinegar tasting
  • Travel by air-conditioned minivan
  • Alcoholic Beverages

About this experience

Discover the picturesque wine region of Chianti on a half-day excursion from Siena. Enjoy the Tuscan scenery of gently undulating hills and vineyards while tasting Chianti wines. A day journey from Siena to the Chianti region allows you to experience the gorgeous Tuscan landscape. Begin with a visit to Castellina in Chianti, followed by a wine tasting at a nearby vineyard. Immerse yourself in the bright colors of the rolling hills, where the views, smells, and flavors of the region will captivate your senses. Enjoy a stroll in Monteriggioni, a medieval village where time seems to stop. Proceed to another winery in the heart of the Chianti Classico region, where you can have a second wine tasting and sample extra virgin olive oil. A return trip to Siena marks the end of the excursion.

What's included

Included

  • Visit two wineries in the Chianti area
  • Expert multilingual guides
  • Wine, oil and balsamic vinegar tasting
  • Travel by air-conditioned minivan
  • Alcoholic Beverages

Not included

  • Gratuities
  • Lunch

What you'll see and do

  1. Siena

    Start you trip form Siena at Via Giuseppe Garibaldi 72, where you will meet our driver. You will travel by minivan to reach the first point of interest.

    30 minutes here

  2. Castellina In Chianti

    Castellina in Chianti enchants with its historic allure, surrounded by picturesque landscapes and tantalizing Tuscan cuisine, offering a timeless escape into the heart of Italy. Admire the medieval Rocca and the church.

    60 minutes here

  3. Strada Statale 222 Chiantigiana

    Enjoy a wine tasting in an evocative winery in the Chianti area.

    60 minutes here · Admission included

  4. Monteriggioni

    Enjoy a free visit of Monteriggioni city inside the walls. The castle of Monteriggioni dates back to the second two decades of the 13th century and was founded by the Republic of Siena.

    60 minutes here

  5. Strada Statale 222 Chiantigiana

    Enjoy a wine tasting in which you can taste the famous Chianti wine typical of this area surrounded by a beautiful landscape.

    60 minutes here · Admission included

  6. Siena

    Return back to Siena on board off the minivan and the driver will drop you off at Via Giuseppe Garibaldi, 72.

    30 minutes here

Where it starts and ends

Meeting point

Siena

Meet our driver in front of Hotel Minerva.

Hotel pickup

No pickup: everyone meets at the start point.

Ends at

Meet our driver in front of Hotel Minerva.

Options you can book

  • SUMMER

  • WINTER

Before you book

Cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Languages
en, it, es
Ticket
Mobile Only
Runs on
Every day
Group size
Up to 8 travelers per booking
Operated by
MyLuxuryDrive

Know before you go

  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Only Adult 18 years old and above are allowed for wine and any other alcoholic beverages

Photos

Chianti and Castles Tour from Siena Small Group in Siena, photo 2Chianti and Castles Tour from Siena Small Group in Siena, photo 3Chianti and Castles Tour from Siena Small Group in Siena, photo 4Chianti and Castles Tour from Siena Small Group in Siena, photo 5Chianti and Castles Tour from Siena Small Group in Siena, photo 6Chianti and Castles Tour from Siena Small Group in Siena, photo 7

Good to know

Duration
5 hours
Free cancellation
Up to 24h before
Minimum age to book
All ages
Availability
Bookable today
Runs on
Every day
Price range
$43 to $85
Hotel pickup
No pickup, meet at start point
Booked in 30 days
2
Verdict
Worth a Look

Why this scores 59

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

Traveler sentiment (30% weight)62
Review evidence (18% weight)35
Booking momentum (14% weight)23
Value for money (12% weight)100
Listing quality (10% weight)100
Local standing (8% weight)12
Booking flexibility (8% weight)100

Chianti and Castles Tour from Siena Small Group: questions travelers ask

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

How much does Chianti and Castles Tour from Siena Small Group cost?

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Prices start at $43 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 Chianti and Castles Tour from Siena Small Group take?

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Plan for about 5 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 Chianti and Castles Tour from Siena Small Group worth it?

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It holds an Outty Ranking of 59 out of 100, which we label "Worth a Look". That score blends traveler sentiment (3.6/5 across 7 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 Chianti and Castles Tour from Siena Small Group?

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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 Chianti and Castles Tour from Siena Small Group suitable for kids and families?

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Yes, all ages are welcome. Families should still weigh the 5-hour running time, and strollers are easier on the earlier, quieter departures.

How far in advance should I book Chianti and Castles Tour from Siena Small Group?

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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 5-hour experience runs outdoors or after sunset.

Where does Chianti and Castles Tour from Siena Small Group 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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