Top Siena Tours & Sightseeing

Q: What are the best options for Siena Tours & Sightseeing?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Siena Tours & Sightseeing are: Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch Siena Walking Tour with Audio and Written Guide by a local Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch Private Vespa Tour in Chianti Private Tour: Montalcino Wine Tasting Experience

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

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Siena Tours & Sightseeing are: Siena Scavenger Hunt & Highlights Self-Guided Walking Tour Siena Walking Tour with Audio and Written Guide by a local Private Guided Tour of Siena with a Licensed Local Tour Guide Italian Opera in Siena Experience E-Bike rental in Tuscany View all kid-friendly Tours →

Q: Which Siena Tours & Sightseeing have Instant Confirmation?

Siena Tours & Sightseeing with Instant Confirmation include: Siena Scavenger Hunt & Highlights Self-Guided Walking Tour Siena Walking Tour with Audio and Written Guide by a local Siena Highlights Private Walking Tour With A Guide (Private Tour) Italian Opera in Siena Experience E-Bike rental in Tuscany View all Tours with Instant Confirmation →

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 →

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)

from
$136

Discover the Chianti Classico wines from an eTuk, from which you can enjoy the a drive through the vineyard covered hills around Siena to a …More

5.0 (11)

Wine Tuk Tour Siena

Discover the Chianti Classico wines from an eTuk, from which you can enjoy the a drive through the vineyard covered hills around Siena to a...

3 hours

5.0 (11)

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

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

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

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)

from
$171

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

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

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

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

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

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

Uncover the soul of Tuscany on this 8-hour private tour through three of its most iconic towns: Siena, San Gimignano, and Monteriggioni. Travel in style …More

Siena, San Gimignano and Monteriggioni Wine Tasting and Tour

Uncover the soul of Tuscany on this 8-hour private tour through three of its most iconic towns: Siena, San Gimignano, and Monteriggioni. Travel in style...

8 hours Free Cancellation

from
$196

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

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
$204

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
$207

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 (338)

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 (338)

from
$216

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 (83)

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 (83)

from
$216

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 (67)

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 (67)

from
$216

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 (198)

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 (198)

from
$217

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 (41)

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 (41)

from
$217