Top Siena Luxury Tours

Q: What are the best options for Siena Luxury Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Siena Luxury Tours are: Siena Tour and exclusive window on Piazza del Campo Private Grape stomping at Chianti Farmhouse Exciting ATV tour in the Tuscan countryside Siena Street Food Tour With 4 or more Tastings Chianti Classico E-Bike Tour

Q: What are the best kid-friendly options for Siena Luxury Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Siena Luxury Tours are: Three Hours Siena Private Walking Tour with Personal Photographer Private Off Road Wine Tour in Chianti from Siena Private wine tour of Chianti Private Montalcino and Pienza Tour from Siena Private Vintage Fiat 500 tour in Chianti From Siena View all kid-friendly Tours →

Q: Which Siena Luxury Tours have Instant Confirmation?

Siena Luxury Tours with Instant Confirmation include: Private Hot Air Balloon to Pienza, Montalcino and Val D'orcia Private Tour: Tuscany Hot Air Balloon Flight from Siena Chianti Wines and San Gimignano Tour from Florence (1 Winery) The Maremma Three Hours Siena Private Walking Tour with Personal Photographer View all Tours with Instant Confirmation →

Q: I need a ride! Which Siena Luxury Tours have Hotel Pickup?

No problem. These Siena Luxury Tours include Hotel Pickup: Brunello/Montalcino-Tour in Ferrari Siena to Rome: Orvieto and Montepulciano Transfer Tour Private Siena to Florence Chianti and San Gimignano Transfer Tour The Maremma Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour View all Tours with Hotel Pickup →

Q: Got any more Siena trip ideas?

We sure do. Check out our curated lists of hand-picked Siena Tours. Top 10 Siena 2026 Senior-friendly tours Siena The best tours and activities for culture lovers in Siena Top Day Trips from Siena Things to do in Siena this summer View all Siena Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Siena?

Based on our sales data over the past year, the most popular styles of tours and activities in Siena are: Siena Cultural & Theme Tours Siena Historical & Heritage Tours Siena Luxury & Special Occasions Siena Luxury Tours Siena Walking & Biking Tours View all tour styles in Siena →

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

* Only small, authentic, family-run activities * Off-the-beaten path itineraries * Private, exclusive, customizable, flexible, door-to-door tour of Pienza, Val d'Orcia, Montalcino * Local, small …More

5.0 (35)

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

* Only small, authentic, family-run activities * Off-the-beaten path itineraries * Private, exclusive, customizable, flexible, door-to-door tour of Pienza, Val d'Orcia, Montalcino * Local, small...

8 hours Hotel pickup offered

5.0 (35)

from
$194

San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from SIENA

* Customizable, door-to-door tour of San Gimignano and Chianti Classico, wine and food Tour from Siena * Private and exclusive service * 8 hours in …More

5.0 (7)

San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from SIENA

* Customizable, door-to-door tour of San Gimignano and Chianti Classico, wine and food Tour from Siena * Private and exclusive service * 8 hours in...

8 hours Hotel pickup offered

5.0 (7)

from
$193

Cycle at your own pace with a local English-speaking guide who can tell you about the area. Admire the famous Chianti Classico wine area close …More

5.0 (2)

Chianti Classico Bike Tour from Siena

Cycle at your own pace with a local English-speaking guide who can tell you about the area. Admire the famous Chianti Classico wine area close...

4 hours

5.0 (2)

from
$184

From Siena: Private Volterra, San Gimignano & Wine Lunch

A private day from Siena to two of the most beautiful hill towns of Tuscany, with a genuine farm lunch in between. • Pick-up at …More

5.0 (4)

From Siena: Private Volterra, San Gimignano & Wine Lunch

A private day from Siena to two of the most beautiful hill towns of Tuscany, with a genuine farm lunch in between. • Pick-up at...

8 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$183

E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles

Embark on an adventure that will take you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in …More

4.7 (19)

E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles

Embark on an adventure that will take you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in...

7 hours 15 minutes Free Cancellation

4.7 (19)

from
$179

San Gimignano, Chianti, and Montalcino Day Trip from Siena

Spend an unforgettable day exploring Italy’s iconic hill-towns and world-class wineries. Starting from Siena, wander the medieval streets of San Gimignano, soak in the vineyards …More

4.5 (125)

San Gimignano, Chianti, and Montalcino Day Trip from Siena

Spend an unforgettable day exploring Italy’s iconic hill-towns and world-class wineries. Starting from Siena, wander the medieval streets of San Gimignano, soak in the vineyards...

11 hours Free Cancellation

4.5 (125)

from
$177

By Ebike: Visit an Art Park and Wine Taste in the Classic Chianti

E-bike tour that takes you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and …More

5.0 (2)

By Ebike: Visit an Art Park and Wine Taste in the Classic Chianti

E-bike tour that takes you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and...

5 hours 20 minutes Free Cancellation

5.0 (2)

from
$176

Exclusive Wine Tour and Tasting Experience in Siena

Just 2 km from the old town of medieval Siena, in the stunning hilly Tuscan countryside, the exclusive wine tour with tasting ‘Land, Climate and …More

5.0 (19)

Exclusive Wine Tour and Tasting Experience in Siena

Just 2 km from the old town of medieval Siena, in the stunning hilly Tuscan countryside, the exclusive wine tour with tasting ‘Land, Climate and...

3 hours 30 minutes Free Cancellation

5.0 (19)

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$171

Discover the secrets of the most authentic Tuscan Maremma, guided by expert Maremmagica personnel, immersed in the uncontaminated nature of the Diaccia Botrona Regional Nature …More

5.0 (1)

Walking tour in Diaccia Botrona

Discover the secrets of the most authentic Tuscan Maremma, guided by expert Maremmagica personnel, immersed in the uncontaminated nature of the Diaccia Botrona Regional Nature...

2 to 3 hours Free Cancellation

5.0 (1)

from
$163

San Gimignano, Chianti and Montalcino Tour through Tuscan wine

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a …More

4.8 (9)

San Gimignano, Chianti and Montalcino Tour through Tuscan wine

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a...

11 hours Free Cancellation

4.8 (9)

from
$159

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

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
$149

Siena E-Tuk Tuk panoramic Aperitivo with Local Snacks

Hop aboard our eco-friendly electric tuk tuk and embark on a panoramic journey around Siena. As you wind your way through the picturesque hills surrounding …More

5.0 (1)

Siena E-Tuk Tuk panoramic Aperitivo with Local Snacks

Hop aboard our eco-friendly electric tuk tuk and embark on a panoramic journey around Siena. As you wind your way through the picturesque hills surrounding...

2 hours

5.0 (1)

from
$149

Siena to Florence Private Transfer: Monteriggioni & San Gimignano

Turn your transfer from Siena to Florence into a visit to two of the most famous medieval towns of Tuscany, crossing the Chianti area, in …More

5.0 (3)

Siena to Florence Private Transfer: Monteriggioni & San Gimignano

Turn your transfer from Siena to Florence into a visit to two of the most famous medieval towns of Tuscany, crossing the Chianti area, in...

5 hours Hotel pickup offered Free Cancellation

5.0 (3)

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$137

The Cathedral of Siena is an overwhelming monument that houses works of art from the Middle Ages to the contemporary period. Inside the church you …More

5.0 (2)

Siena Cathedral: Private Tour

The Cathedral of Siena is an overwhelming monument that houses works of art from the Middle Ages to the contemporary period. Inside the church you...

1 hour Free Cancellation

5.0 (2)

from
$136

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
$135

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 (94)

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 (94)

from
$125

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany

If you choose to see the Medieval Tuscany with us, after meeting you in front of your residence, we will take you with a short …More

5.0 (14)

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany

If you choose to see the Medieval Tuscany with us, after meeting you in front of your residence, we will take you with a short...

8 to 9 hours Free Cancellation

5.0 (14)

from
$122

On this private walking tour you will explore a city declared a UNESCO World Heritage Site. You will visit its most important places, such as …More

5.0 (2)

Siena Private Walking Tour

On this private walking tour you will explore a city declared a UNESCO World Heritage Site. You will visit its most important places, such as...

2 to 3 hours Free Cancellation

5.0 (2)

from
$115

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)