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Top Siena Private & Custom Tours

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Siena Tours

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Siena Medieval Power Quest: Self-Guided Family Feud Game

Unravel the secrets of medieval Siena through a thrilling quest of power, rivalry, and hidden history. This isn’t just a walk - it’s an adventure …More

4.2 (26)

Siena Medieval Power Quest: Self-Guided Family Feud Game

Unravel the secrets of medieval Siena through a thrilling quest of power, rivalry, and hidden history. This isn’t just a walk - it’s an adventure...

60 to 90 minutes • Free Cancellation
4.2 (26)
from
$8
Private Tour of Siena Cathedral

In Piazza Duomo stands the imposing Cathedral of Siena and right here you will begin the visit. After an introduction about the extraordinary façade decorated …More

5.0 (19)

Private Tour of Siena Cathedral

In Piazza Duomo stands the imposing Cathedral of Siena and right here you will begin the visit. After an introduction about the extraordinary façade decorated...

2 hours • Free Cancellation
5.0 (19)
from
$32
Discover the Medieval Charm of Siena on a Private Walking Tour

Decide with your guide if you want to have a 2 or 3 hours tour! Discover the treasures of one of the most beautiful cities …More

4.8 (174)

Discover the Medieval Charm of Siena on a Private Walking Tour

Decide with your guide if you want to have a 2 or 3 hours tour! Discover the treasures of one of the most beautiful cities...

2 to 3 hours • Free Cancellation
4.8 (174)
from
$36
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
$315
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
$208
Siena Private Walking Tour: Traditions, Streets & Cathedral

Explore Siena on a private walking tour with an expert local guide and discover the city beyond the main tourist routes. Walk through the historic …More

4.6 (78)

Siena Private Walking Tour: Traditions, Streets & Cathedral

Explore Siena on a private walking tour with an expert local guide and discover the city beyond the main tourist routes. Walk through the historic...

2 to 3 hours • Free Cancellation
4.6 (78)
from
$115
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
Private Tour: Montalcino Wine Tasting Experience

Private guided wine tour and tasting in Montalcino, Tuscany to discover Brunello and the most amazing wine estates and cellars that give birth to this …More

Likely to Sell Out
Likely to Sell Out
5.0 (71)

Private Tour: Montalcino Wine Tasting Experience

Private guided wine tour and tasting in Montalcino, Tuscany to discover Brunello and the most amazing wine estates and cellars that give birth to this...

8 hours • Hotel pickup offered • Free Cancellation
5.0 (71)
from
$313
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 (108)

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 (108)
from
$325
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
$254
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
$262
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
$254
Siena Cathedral: shrine of treasures.

The guided visit of the Cathedral and its floor is a journey full of excitement. Come with Tuscany Art Trek and enjoy nearly a thousand …More

Likely to Sell Out
Likely to Sell Out
4.8 (10)

Siena Cathedral: shrine of treasures.

The guided visit of the Cathedral and its floor is a journey full of excitement. Come with Tuscany Art Trek and enjoy nearly a thousand...

1 hour 30 minutes • Free Cancellation
4.8 (10)
from
$151
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
$277
PRIVATE TOUR: Florence & Chianti in one day with Lunch and Tasting in Winery

Begin your day in the magical city of Florence, the Renaissance jewel. Marvel at the panoramic masterpiece from Piazzale Michelangelo, capturing the essence of this …More

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

PRIVATE TOUR: Florence & Chianti in one day with Lunch and Tasting in Winery

Begin your day in the magical city of Florence, the Renaissance jewel. Marvel at the panoramic masterpiece from Piazzale Michelangelo, capturing the essence of this...

9 hours • Hotel pickup offered • Free Cancellation
5.0 (2)
from
$209
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
$343
PRIVATE TOUR: Full-Day Volterra & San Gimignano with Wine Tasting Experience

Spend a day visiting Volterra with its splendid Roman Theater and the "Beautiful Towers" of San Gimignano. A trip from the Etruscan period to the …More

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

PRIVATE TOUR: Full-Day Volterra & San Gimignano with Wine Tasting Experience

Spend a day visiting Volterra with its splendid Roman Theater and the "Beautiful Towers" of San Gimignano. A trip from the Etruscan period to the...

7 hours • Hotel pickup offered • Free Cancellation
5.0 (4)
from
$197
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
$300
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
$139
PRIVATE TOUR: Savor Exquisite Wines: Brunello & Nobile Wine Tour

A superb Experience in the wonderful Val d'Orcia between Noble vines & Medieval cities • Our driver escort will pick you up at your location …More

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

PRIVATE TOUR: Savor Exquisite Wines: Brunello & Nobile Wine Tour

A superb Experience in the wonderful Val d'Orcia between Noble vines & Medieval cities • Our driver escort will pick you up at your location...

9 hours • Hotel pickup offered • Free Cancellation
5.0 (3)
from
$208

Frequently Asked Questions

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

Recent tour reviews
Bella Siena
New York City
Siena Private Walking Tour: Traditions, Streets & Cathedral
Juan_R, Sep 2026
Bella Siena
Anna was amazing! She provided a lot of historical, political and religious context to allow us to better understand the beauty of Siena.
Read more
Best tour of Siena
New York City
Private Tour: Secret Siena Walking Tour
Mary_P, Sep 2026
Best tour of Siena
We thoroughly enjoyed our morning with Elio seeing the sights in Siena. He was incredibly knowledgeable about the Siena contrada, and especially the Siena Duomo. We learned so much more about its history, mosaics and art than we would have on our own. Highly recommend this experience in Siena
Read more
Memories are made…….
New York City
Private Tour: Montalcino Wine Tasting Experience
cherylvX8031GE, Sep 2026
Memories are made…….
This is our second time in Cortona using this vendor and have the same guide, Francesco. Such good memories made the first time we did it again because of his knowledge and professionalism. I highly recommend if you are planning a visit to the area!
Read more
Great wine day with Francesco!
New York City
Private Tour: Montalcino Wine Tasting Experience
T952TMalisonb, Sep 2026
Great wine day with Francesco!
Francesco was absolutely wonderful! He was fun, knowledgeable and easy going. We had a great afternoon learning about wine and all things Italy! Would highly recommend!
Read more
Great walking tour
New York City
Private Tour: Siena Walking Tour
G2802AIseanc, Sep 2026
Great walking tour
Silvia was a great guide for our walking tour in Siena. Her deep knowledge of the city's architecture, history, the Contrade, and the Palio brought the streets to life in a way we never could have experienced on our own. She is engaging, knowledgeable and highly professional. If you are visiting Siena, you should book a tour with Silvia!
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
Excellent private tour for families. Get to know Siena and its districts.
New York City
Private Tour: Siena Walking Tour
marinao723, Aug 2026
Excellent private tour for families. Get to know Siena and its districts.
Silvia Roncucci was helpful and thorough. During the tour with my family (my husband and three teenage children) we had fun and learned many anecdotes and stories related not only to the art of Siena but also to the culture and the Palio. It was a fascinating and new experience.
Read more
Beautiful town with incredible history, born place for the first bank and importaand gorgeous cathedral
New York City
Siena Cathedral: shrine of treasures.
245olegv, Aug 2026
Beautiful town with incredible history, born place for the first bank and importaand gorgeous cathedral
Absolutely wonderful tour through this historic city, very good and interesting story about Palio, very beautiful cathedral with Michelangelo and Bernini works, nice small streets and atmosphere of medieval ages.
Read more
Excellent tour in Siena
New York City
Discover the Medieval Charm of Siena on a Private Walking Tour
Thomas_F, Aug 2026
Excellent tour in Siena
Ludovica was wonderful We learned so much about Siena and the Palio. She was patient, cheerful and knowledgeable.
Read more
Wonderful & informative tour!!
New York City
Discover the Medieval Charm of Siena on a Private Walking Tour
TinaMutoWong, Aug 2026
Wonderful & informative tour!!
Barbara was a wonderful guide. She taught us so much about the history & culture of Sienna. We totally enjoyed our tour & she was very accommodating to our different members.
Read more
Artistic perfection from floor to ceiling!
New York City
Siena Cathedral: shrine of treasures.
647angelikic, Jul 2026
Artistic perfection from floor to ceiling!
A magnificent cathedral! Its interior is so grand that it can only be compared to St. Peter's Basilica in Rome. The cathedral boasts a spectacular floor of inlaid marble masterpieces with graffito details, exquisite sculptures (including works by Michelangelo), beautiful icons, monumental colorful frescoes, and a vast collection of 15th-century choral manuscripts. It is an absolute must-visit for anyone traveling to Siena.
Read more
Amazing fun
New York City
Private Off Road Wine Tour in Chianti from Siena
Amol_S, Jul 2026
Amazing fun
The tourist fun especially travelling the backroads that are gravel... It's truly a great experience
Read more
Best ever
New York City
Siena Medieval Power Quest: Self-Guided Family Feud Game
Cimetka, Oct 2025
Best ever
Absolutely the best scavenger hunt game ever!!! it was the first one for us and none so far have reached its level! We almost forgot to see the city, we were so enchanted with the game :-) absolutely recommend it!!
Read more
Group of 12 had a great time touring Tuscany
New York City
PRIVATE TOUR: Savor Exquisite Wines: Brunello & Nobile Wine Tour
Pioneer03928340575, Sep 2025
Group of 12 had a great time touring Tuscany
We had a blast with the PEK team (We were a group of 1e. Very knowledgeable and entertaining. We will surely rebook this team next time. Thank you Andrea and team.
Read more
Fantastic tour that brought historic Siena to life in a most engaging way.
New York City
Private Tour of Siena Cathedral
wyards, Sep 2025
Fantastic tour that brought historic Siena to life in a most engaging way.
Fantastic tour. Barbara Latini was extremely knowledgable and engaging and made the tour an absolute delight. Because she could see how our small group of 5 was so interested, she continued well beyond the allotted time. Very highly recommended
Read more
Wonderful guided tour of the Duomo
New York City
Private Tour of Siena Cathedral
gianchi83, Sep 2025
Wonderful guided tour of the Duomo
The specialized guide Elena accompanied us on a two-hour visit of the cathedral of Siena. The visit was incredibly engaging thanks to Elena's professionalism that combines an immense knowledge of the subject with a great ability to transmit and also a nice and friendly attitude. We hope that more and more people will enjoy the experience of having Elena as their guide.
Read more
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