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Top Siena Tours & Sightseeing

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Siena Tours

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Siena: Val d’Orcia Wine Tour with Lunch & Brunello

Discover the enchanting allure of Tuscany's most renowned winery region, where every step through the picturesque landscapes of Pienza and Montepulciano is a delightful fusion …More

4.1 (81)

Siena: Val d’Orcia Wine Tour with Lunch & Brunello

Discover the enchanting allure of Tuscany's most renowned winery region, where every step through the picturesque landscapes of Pienza and Montepulciano is a delightful fusion...

10 to 11 hours • Free Cancellation
4.1 (81)
from
$127
Small-Group Montepulciano and Pienza Day Trip from Siena

Experience the heart of Tuscany on this guided small-group tour day trip to the charming towns of Pienza and Montepulciano. Travel through the beautiful clay …More

4.9 (325)

Small-Group Montepulciano and Pienza Day Trip from Siena

Experience the heart of Tuscany on this guided small-group tour day trip to the charming towns of Pienza and Montepulciano. Travel through the beautiful clay...

8 hours • Free Cancellation
4.9 (325)
from
$221
Small-Group San Gimignano and Volterra Day Trip from Siena

Embrace the medieval charms of Tuscany's towns on a full-day trip to San Gimignano and Volterra from Siena. With an attentive local guide, walk round …More

4.9 (191)

Small-Group San Gimignano and Volterra Day Trip from Siena

Embrace the medieval charms of Tuscany's towns on a full-day trip to San Gimignano and Volterra from Siena. With an attentive local guide, walk round...

8 hours • Free Cancellation
4.9 (191)
from
$221
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
$98
Private Tour: Siena Walking Tour

Siena, 'the pearl of the Gothic style,' is a charming medieval town in the center of Tuscany. Come and discover the hidden treasures of this medieval …More

Likely to Sell Out
Likely to Sell Out
5.0 (43)

Private Tour: Siena Walking Tour

Siena, 'the pearl of the Gothic style,' is a charming medieval town in the center of Tuscany. Come and discover the hidden treasures of this medieval...

2 hours • Free Cancellation
5.0 (43)
from
$209
San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Experience Tuscany in a day from Florence: San Gimignano, Monteriggioni, Chianti, and Siena. 11-hour coach tour through medieval towers, walled hamlets, and rolling vineyards. Explore …More

4.6 (173)

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Experience Tuscany in a day from Florence: San Gimignano, Monteriggioni, Chianti, and Siena. 11-hour coach tour through medieval towers, walled hamlets, and rolling vineyards. Explore...

11 hours • Free Cancellation
4.6 (173)
from
$83
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
$317
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
$110
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
Small-Group Chianti and San Gimignano Sunset Trip from Siena

On this afternoon and evening tour from Siena to Chianti and San Gimignano, explore the beautiful Chianti region – an area rich with dense oak …More

4.8 (65)

Small-Group Chianti and San Gimignano Sunset Trip from Siena

On this afternoon and evening tour from Siena to Chianti and San Gimignano, explore the beautiful Chianti region – an area rich with dense oak...

8 to 9 hours • Free Cancellation
4.8 (65)
from
$221
Small-Group Chianti Trip with Wine Tasting from Siena

Combine Chianti's fine wines with its impressive castles on a full-day trip from Siena! Giving the rugged Tuscan landscape a remarkable grandeur, these stunning Italian …More

5.0 (82)

Small-Group Chianti Trip with Wine Tasting from Siena

Combine Chianti's fine wines with its impressive castles on a full-day trip from Siena! Giving the rugged Tuscan landscape a remarkable grandeur, these stunning Italian...

8 hours • Free Cancellation
5.0 (82)
from
$220
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

Likely to Sell Out
Likely to Sell Out
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
Italian Opera in Siena Experience

Enjoy a wonderful journey into the opera culture of Italy in charming, intimate surroundings, in Siena’s historical centre. Our singers will perform famous pieces from …More

4.8 (65)

Italian Opera in Siena Experience

Enjoy a wonderful journey into the opera culture of Italy in charming, intimate surroundings, in Siena’s historical centre. Our singers will perform famous pieces from...

1 hour 20 minutes • Free Cancellation
4.8 (65)
from
$37
Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch

Our driver guide will collect you at the designated meeting point, setting off toward Montalcino. Start this full-day tour with a lesser-known boutique vineyard with …More

4.9 (107)

Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch

Our driver guide will collect you at the designated meeting point, setting off toward Montalcino. Start this full-day tour with a lesser-known boutique vineyard with...

8 hours • Hotel pickup offered • Free Cancellation
4.9 (107)
from
$266
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
$406
Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch

To fully experience la "Bella vita", you need to get out of the city. Taste the local wines & tour the cellars of select family-run, …More

4.9 (77)

Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch

To fully experience la "Bella vita", you need to get out of the city. Taste the local wines & tour the cellars of select family-run,...

6 to 8 hours • Hotel pickup offered • Free Cancellation
4.9 (77)
from
$289
VIP Chianti, Brunello wine & Pienza with lunch From Siena

This is a semi- private with maximum 6 people in tour so you will have all the attention you need. This tours will give you …More

5.0 (27)

VIP Chianti, Brunello wine & Pienza with lunch From Siena

This is a semi- private with maximum 6 people in tour so you will have all the attention you need. This tours will give you...

8 to 9 hours • Free Cancellation
5.0 (27)
from
$273
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
$209
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
$220
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
$360

Frequently Asked Questions

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

Recent tour reviews
Outstanding
New York City
Small-Group San Gimignano and Volterra Day Trip from Siena
John_D, Sep 2026
Outstanding
Our guide was outstanding. I am usually not very lavish with praise. This fellow did an excellent job. Very glad we booked the adventure.
Read more
We had an amazing day...
New York City
San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
David_R, Sep 2026
We had an amazing day...
We had an amazing day with Lily touring multiple different places throughout Tuscany. I can’t say enough about how great Lily was to work with and how fun she made the day. I would highly recommend this Danny one that’s considering it.
Read more
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
Great experience
New York City
Small-Group Montepulciano and Pienza Day Trip from Siena
Laneth1101, Sep 2026
Great experience
This was the best tour we’ve had so far on our Italian vacation. Our guide, Marco was amazing! He was so knowledgeable, friendly and funny. He took us to the best little hidden gem spots and the farm we had lunch at was so quaint and the food was delicious. Highly recommend this tour to anyone! If you’re on the fence, just book it you’ll be glad you did!
Read more
Sofia and Claudio were...
New York City
Siena: Val d’Orcia Wine Tour with Lunch & Brunello
Deb_D, Sep 2026
Sofia and Claudio were...
Sofia and Claudio were absolute gems for this tour. Claudeo's driving and Sofia's personal and knowledge were highlights of the trip. The visit to the three cities and vineyards was worth the trip and time. Thank you to Sofia & Claudio for a marvelous day!!
Read more
Lovely Tuscany; small medium and grand
New York City
Small-Group Montepulciano and Pienza Day Trip from Siena
k_n, Sep 2026
Lovely Tuscany; small medium and grand
Informative, historical and varied. As we rode through the Tuscan countryside stirring at a small village, medium town and powerful city, our guide Keko explained localities, crops, landscapes, nobility, architecture, and produce of the area.
Read more
Big day out
New York City
San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
Alan_M, Sep 2026
Big day out
Lily was a great guide. Amazing day well managed and plenty of free time in each location. It is a big day so pace yourself
Read more
Incredible tour of Brunello Wineries
New York City
Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch
P850EBkristinm, Sep 2026
Incredible tour of Brunello Wineries
It was amazing! Our guide, Nico, who is also the owner brought us to two wonderful wineries! I initially scheduled with another company and they cancelled last minute and I am so glad they did. We had the best time and our experience was terrific. Nico told us about how the Brunello area wines are and then we got a tour and tasting at the first winery all run by the owner’s daughter. After that, we went to the most delicious lunch and tasting at another winery. After that Nico brought us straight to our door. I felt safe because he was a great driver and we learned so much and laughed often. I will definitely contact Tours of Tuscany next time we come to Italy. The quality was a 5/5
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
Best of Tuscany wines & lunch in Montepulciano
New York City
Siena: Val d’Orcia Wine Tour with Lunch & Brunello
O9722SIpamelal, Sep 2026
Best of Tuscany wines & lunch in Montepulciano
The trip was very good. Sofi is an excellent guide. Lots of interesting information about all the areas we travelled through and the 3 towns we visited. She was fun, welcoming and happy to answer any questions.Claudio the driver was also excellent. Picked up on time and was always exactly where we told to meet him.
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
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