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Top Siena Half-day Tours

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Siena Tours

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Siena: A Wine Tour and Tasting Experience

In the hills of the gorgeous Tuscan countryside,  just 2kms away from the medieval center of Siena, this Educational Wine Tour and Tasting 'Vine, Wine …More

5.0 (364)

Siena: A Wine Tour and Tasting Experience

In the hills of the gorgeous Tuscan countryside,  just 2kms away from the medieval center of Siena, this Educational Wine Tour and Tasting 'Vine, Wine...

3 hours • Free Cancellation
5.0 (364)
from
$99
Private Off Road Wine Tour in Chianti

Discover the highlights of Chianti Classico while riding through Tuscany’s backroads in a Land Rover Defender. There is a special kind of magic in driving …More

Likely to Sell Out
Likely to Sell Out
5.0 (20)

Private Off Road Wine Tour in Chianti

Discover the highlights of Chianti Classico while riding through Tuscany’s backroads in a Land Rover Defender. There is a special kind of magic in driving...

6 hours • Free Cancellation
5.0 (20)
from
$319
Siena: Chianti Sunset Tour with Dinner & Wine Tasting

There are many ways to spend an evening in Tuscany, but few allow you to experience it from the inside. Just a few minutes from …More

Likely to Sell Out
Likely to Sell Out
5.0 (49)

Siena: Chianti Sunset Tour with Dinner & Wine Tasting

There are many ways to spend an evening in Tuscany, but few allow you to experience it from the inside. Just a few minutes from...

3 hours • Free Cancellation
5.0 (49)
from
$111
Hidden Castles & Chianti Wine Experience– Small Group

Visit two charming family-run wineries in the heart of the Chianti region, learn about local winemaking traditions, and taste 7 exquisite wines paired with bruschetta, …More

4.6 (155)

Hidden Castles & Chianti Wine Experience– Small Group

Visit two charming family-run wineries in the heart of the Chianti region, learn about local winemaking traditions, and taste 7 exquisite wines paired with bruschetta,...

5 hours • Free Cancellation
4.6 (155)
from
$57
Highlights & Hidden Gems of Siena Private Tour - Duomo Included

Siena is a magical place! And with the local host, you are going to experience it all. So get ready; culture, history, and local lifestyle …More

5.0 (19)

Highlights & Hidden Gems of Siena Private Tour - Duomo Included

Siena is a magical place! And with the local host, you are going to experience it all. So get ready; culture, history, and local lifestyle...

3 hours • Free Cancellation
5.0 (19)
from
$72
Small group Chianti Classico & Brunello wine region from Siena

This is a semi-private which means a maximum of 6 people in tour, so you will have a private vehicle and all the attention you …More

4.9 (31)

Small group Chianti Classico & Brunello wine region from Siena

This is a semi-private which means a maximum of 6 people in tour, so you will have a private vehicle and all the attention you...

5 hours 30 minutes • Free Cancellation
4.9 (31)
from
$210
Small Group E-Bike Chianti Tour with farm lunch from Siena

Follow your experienced guide on a ride through the Chianti hills on comfortable and easy to use Electric Bikes: you must have cycling experience to …More

4.8 (39)

Small Group E-Bike Chianti Tour with farm lunch from Siena

Follow your experienced guide on a ride through the Chianti hills on comfortable and easy to use Electric Bikes: you must have cycling experience to...

6 hours • Free Cancellation
4.8 (39)
from
$221
Hot Air Balloon Flight Over Tuscany from Siena

Admire the stunning landscapes of Tuscany from above on an approximately 1-hour hot air balloon flight over the hills of Siena. This is both a …More

4.9 (123)

Hot Air Balloon Flight Over Tuscany from Siena

Admire the stunning landscapes of Tuscany from above on an approximately 1-hour hot air balloon flight over the hills of Siena. This is both a...

3 hours • Free Cancellation
4.9 (123)
from
$359
Private Tour: Secret Siena Walking Tour

Discover the older parts of Siena’s medieval centre and see hidden corners away from the crowded tourist areas, an exceptional itinerary to discover the quieter …More

4.9 (107)

Private Tour: Secret Siena Walking Tour

Discover the older parts of Siena’s medieval centre and see hidden corners away from the crowded tourist areas, an exceptional itinerary to discover the quieter...

3 hours • Free Cancellation
4.9 (107)
from
$328
Siena Walking Tour with Audio and Written Guide by a local

If you're looking for a fun and curious way to visit Siena, you've come to the right place! With this digital guide created with the …More

4.4 (41)

Siena Walking Tour with Audio and Written Guide by a local

If you're looking for a fun and curious way to visit Siena, you've come to the right place! With this digital guide created with the...

4 to 5 hours • Free Cancellation
4.4 (41)
from
$6
Private Grape stomping at Chianti Farmhouse

Harvest has always been seen as a time of celebration in the countryside: after months of hard work and sacrifices, all those efforts are finally …More

Likely to Sell Out
Likely to Sell Out
4.9 (11)

Private Grape stomping at Chianti Farmhouse

Harvest has always been seen as a time of celebration in the countryside: after months of hard work and sacrifices, all those efforts are finally...

4 hours • Free Cancellation
4.9 (11)
from
$256
Private Truffle Hunting in Chianti

The Tuscan hills hide real treasures, and we will guide you on an unforgettable tour through the Chianti woods. Discover the secrets of truffles, their …More

Likely to Sell Out
Likely to Sell Out
5.0 (5)

Private Truffle Hunting in Chianti

The Tuscan hills hide real treasures, and we will guide you on an unforgettable tour through the Chianti woods. Discover the secrets of truffles, their...

5 hours • Free Cancellation
5.0 (5)
from
$264
Private Vespa Tour in Chianti

While we take care of every detail, leave the chaos behind and enjoy the best of Tuscany’s landscapes from your stylish Vespa — perfect not …More

Likely to Sell Out
Likely to Sell Out
5.0 (7)

Private Vespa Tour in Chianti

While we take care of every detail, leave the chaos behind and enjoy the best of Tuscany’s landscapes from your stylish Vespa — perfect not...

5 hours • Free Cancellation
5.0 (7)
from
$255
Private Ebike Tour in Chianti

Unsurprisingly, Tuscany is one of the favorite destinations for cycling enthusiasts: the views, the scent of the trees along the avenues, and the typical colors …More

Likely to Sell Out
Likely to Sell Out
5.0 (4)

Private Ebike Tour in Chianti

Unsurprisingly, Tuscany is one of the favorite destinations for cycling enthusiasts: the views, the scent of the trees along the avenues, and the typical colors...

6 hours • Free Cancellation
5.0 (4)
from
$279
Private Off Road Wine Tour in Chianti from Siena

Discover the highlights of Chianti Classico riding through Tuscany’s scenic backroads in a 4WD. There’s a certain magic in traveling along the hidden gravel roads, …More

Likely to Sell Out
Likely to Sell Out
5.0 (2)

Private Off Road Wine Tour in Chianti from Siena

Discover the highlights of Chianti Classico riding through Tuscany’s scenic backroads in a 4WD. There’s a certain magic in traveling along the hidden gravel roads,...

6 hours • Hotel pickup offered • Free Cancellation
5.0 (2)
from
$346
Private Vintage Fiat 500 tour in Chianti

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s …More

Likely to Sell Out
Likely to Sell Out
5.0 (2)

Private Vintage Fiat 500 tour in Chianti

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s...

6 hours • Free Cancellation
5.0 (2)
from
$303
PRIVATE TRANSFER from Siena to Florence with stop in S Gimignano & Monteriggioni

Explore the enchanting Chianti region during your trip from Siena to Florence with our expert local driver, aboard a comfortable Minivan with a large trunk. …More

Likely to Sell Out
Likely to Sell Out
5.0 (3)

PRIVATE TRANSFER from Siena to Florence with stop in S Gimignano & Monteriggioni

Explore the enchanting Chianti region during your trip from Siena to Florence with our expert local driver, aboard a comfortable Minivan with a large trunk....

4 hours • Hotel pickup offered • Free Cancellation
5.0 (3)
from
$140
Signature Brunello di Montalcino Wine Tour from Siena

Brunello di Montalcino, widely celebrated as one of the finest wines in the world, is the ultimate expression of a centuries-old winemaking heritage rooted in …More

4.3 (57)

Signature Brunello di Montalcino Wine Tour from Siena

Brunello di Montalcino, widely celebrated as one of the finest wines in the world, is the ultimate expression of a centuries-old winemaking heritage rooted in...

5 hours 30 minutes • Free Cancellation
4.3 (57)
from
$139
Hot air balloon over the hills of Pienza, Montalcino and Val D'Orcia

The hot air balloon tour is a magical experience, a true adventure carried out in total safety by flight professionals. Our pilots, all with great …More

5.0 (20)

Hot air balloon over the hills of Pienza, Montalcino and Val D'Orcia

The hot air balloon tour is a magical experience, a true adventure carried out in total safety by flight professionals. Our pilots, all with great...

3 hours • Free Cancellation
5.0 (20)
from
$408
The Most Delicious Private Food Tour of Siena: 10 Tastings

Fall in love with the flavorful Tuscan cuisine on this private food tour in Siena! Enjoy a selection of 10 food and drink tastings hand-picked …More

5.0 (11)

The Most Delicious Private Food Tour of Siena: 10 Tastings

Fall in love with the flavorful Tuscan cuisine on this private food tour in Siena! Enjoy a selection of 10 food and drink tastings hand-picked...

3 hours • Free Cancellation
5.0 (11)
from
$112

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Excellent tour, great wine and lunch.
New York City
Siena: A Wine Tour and Tasting Experience
Markejbell, Sep 2026
Excellent tour, great wine and lunch.
Great tour, delicicious light lunch and fantastic wine. The guide (Dario) was knowledgeable, humorous and was generous with his time and insight. This is a small Tuscan winery with great traditional and modern wines . Intimate experience with fellow tourists and enthusiasts. If you are looking for a wine tasting experience lasting for around three hours (or more) and find yourself in the Siena area, I could not recommend this more. Oh and the wine is pretty damn good too...
Read more
Exceptional host!!!
New York City
Siena: Chianti Sunset Tour with Dinner & Wine Tasting
marcusc208, Sep 2026
Exceptional host!!!
We were late because of a car breakdown but they were extremely accommodating. We were not able to join the visits but Elena made it all worthwhile at the dinner and wine pairing. We also had two additional guests at the very last minute and they made an exception to accommodate them. It was a wonderful experience and highly recommended.
Read more
Amazing!
New York City
Siena: A Wine Tour and Tasting Experience
trinem851, Sep 2026
Amazing!
Fantastic! Amazing wine, fantastic food and good company! Very informative tour and a beautiful scenery!
Read more
Highly recommend this trip
New York City
Small Group E-Bike Chianti Tour with farm lunch from Siena
Sue_W, Sep 2026
Highly recommend this trip
Route is a little scary riding into and out of the city, but once you are in the countryside it's magical. Our guide Dom, was very patient with all the riders, as there were varying levels of skill. He made everyone feel comfortable. Highly recommend this ride. It's a fabulous way to really see Tuscany.
Read more
An evening of exceptional wine tasting
New York City
Siena: Chianti Sunset Tour with Dinner & Wine Tasting
John_Q, Sep 2026
An evening of exceptional wine tasting
This tour was one of the most knowledgeable and informative tours. The staff and hosts were so friendly and attentive and accommodating. This winery is family owned and so very good. Their tour includes several tasting, walking tour and a fantastic dinner. We would definitely recommend this tour for anyone who enjoys a great relaxing experience that’s engaging and fun
Read more
Great Ride over Tuscany
New York City
Hot Air Balloon Flight Over Tuscany from Siena
Steve_G, Sep 2026
Great Ride over Tuscany
Wonder full experience, first time up in a Hot Air Balloon couldn’t imagine having been any better, awesome crew and pilot.
Read more
Very fun tour. The...
New York City
Small Group E-Bike Chianti Tour with farm lunch from Siena
Bruce_K, Sep 2026
Very fun tour. The...
Very fun tour. The E-Bikes really made the trip easy. Dominic our guide was very informative. Highly recommend
Read more
Excellent small group tour
New York City
Small group Chianti Classico & Brunello wine region from Siena
Stay06739760728, Sep 2026
Excellent small group tour
The tour we did was the highlight of our trip to Tuscany. The tour included outstanding views, wine tasting at a boutique winery with lunch and visits to historical towns. Our guide Morad shared his extensive knowledge and was a very lovely person. Thank You Moro Tuscany Tours. David and Tracy
Read more
Tour of Sienna, Italy was a great experience
New York City
Siena Walking Tour with Audio and Written Guide by a local
debbiehU8532WG, Sep 2026
Tour of Sienna, Italy was a great experience
Easy to follow and figure out.
Read more
Great way to fill in an afternoon in Siena
New York City
Hidden Castles & Chianti Wine Experience– Small Group
Keith_C, Sep 2026
Great way to fill in an afternoon in Siena
Our tour guide was caught in traffic from Florence, but we were kept informed. It wasn't a small group, we had about 25. The tour was fantastic with plenty of time at each stop. It went overtime, which was excellent value for money. Our guide was a little shy with limited English, and could have given more info en route. Overall... woukd recommend.
Read more
Great wine and good vibes
New York City
Hidden Castles & Chianti Wine Experience– Small Group
Liviu_C, Sep 2026
Great wine and good vibes
Valesca has a cheerful and positive energy. Your experience through Tuscany will only get better with her and Massimo as guides. Highly recommend.
Read more
The best way to experience Siena
New York City
Private Tour: Secret Siena Walking Tour
terim5332022, Sep 2026
The best way to experience Siena
Claudia was an amazing tour guide and a highlight of our time in Siena.
Read more
Dream come true
New York City
Hot Air Balloon Flight Over Tuscany from Siena
tina_barreto, Sep 2026
Dream come true
It was a dream come true ! Perfect from start to beginning! Bucket list done
Read more
relaxed style of a tour.
New York City
Siena Walking Tour with Audio and Written Guide by a local
dr-umatthies, Aug 2026
relaxed style of a tour.
The contact went smoothly. We really liked the option of being guided through Siena according to our own taste—listening, pausing, having a drink, listening again…—it was a very relaxed way to be guided. The only fly in the ointment: I would have liked more information in terms of content.
Read more
Great tour
New York City
Private Tour: Secret Siena Walking Tour
Mary_V, Aug 2026
Great tour
Georgia was highly informative. Loved how she provided us with so much history. We learned so much about the neighborhoods and the horse races.
Read more
We had a tour with Idania...
New York City
The Most Delicious Private Food Tour of Siena: 10 Tastings
allie_h, Aug 2026
We had a tour with Idania...
Idania had great information to give us as we wondered the city and tried different foods.
Read more
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