Top Siena Luxury Tours

Q: Which Siena Luxury Tours have Instant Confirmation?

Siena Luxury Tours with Instant Confirmation include: Skip the Line: Siena Duomo and City Walking Tour Siena: A Wine Tour and Tasting Experience Discover the Medieval Charm of Siena on a Private Walking Tour Hot Air Balloon Flight Over Tuscany from Siena Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch 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 di Montalcino Wine Tour of 2 Wineries with Pairing Lunch Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch Private Tour: Montalcino Wine Tasting Experience Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA 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 →

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

Two magic hours to discover the city with Your children! Children and adults will learn the city's history having fun and being enriched by anecdotes …More

4.8 (10)

Siena Family Tour

Two magic hours to discover the city with Your children! Children and adults will learn the city's history having fun and being enriched by anecdotes...

2 hours Free Cancellation

4.8 (10)

from
$33

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan …More

5.0 (10)

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan...

8 hours Hotel pickup offered

5.0 (10)

from
$227

Horseback Riding in the Tuscan Vineyards

Open the doors of the Sienese countryside on horseback and immerse yourself in the breathtaking landscapes of the Tuscan countryside. Cross vineyards, rivers, olive groves …More

4.8 (10)

Horseback Riding in the Tuscan Vineyards

Open the doors of the Sienese countryside on horseback and immerse yourself in the breathtaking landscapes of the Tuscan countryside. Cross vineyards, rivers, olive groves...

1 hour Free Cancellation

4.8 (10)

from
$74

Siena walking tour with Gelato & Prosecco

This is a city walking tour that will give you the occasion the see this city from the eyes of a local. Your Guide is …More

4.9 (9)

Siena walking tour with Gelato & Prosecco

This is a city walking tour that will give you the occasion the see this city from the eyes of a local. Your Guide is...

1 hour 30 minutes Free Cancellation

4.9 (9)

from
$62

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 with me the unknown and most fascinating Siena with this unique and unusual tour. SECRET SIENA WALKING TOUR, is my favorite to discover history, …More

4.8 (9)

Secret Siena Walking Tour

Discover with me the unknown and most fascinating Siena with this unique and unusual tour. SECRET SIENA WALKING TOUR, is my favorite to discover history,...

2 hours Free Cancellation

4.8 (9)

from
$258

Wine Tasting ATV tour in Tuscan countryside

ATV Excursion in the hearth of Tuscany, in province of Siena, in Crete Senesi UNESCO heritage, between Chianti and Val d'Orcia …More

5.0 (9)

Wine Tasting ATV tour in Tuscan countryside

ATV Excursion in the hearth of Tuscany, in province of Siena, in Crete Senesi UNESCO heritage, between Chianti and Val d'Orcia...

4 hours Free Cancellation

5.0 (9)

from
$365

Private Guided Tour of Siena with a Licensed Local Tour Guide

Together we will embark on a journey going back in time to discover the fascinating history of one of the greatest Medieval cities in Italy. …More

5.0 (9)

Private Guided Tour of Siena with a Licensed Local Tour Guide

Together we will embark on a journey going back in time to discover the fascinating history of one of the greatest Medieval cities in Italy....

2 hours Free Cancellation

5.0 (9)

from
$31

Private Siena to Florence Chianti and San Gimignano Transfer Tour

Travel between destinations and visit sights along the way. Stop to visit the medieval fortress of Monteriggioni before spending leisure time in the hill-town of …More

5.0 (9)

Private Siena to Florence Chianti and San Gimignano Transfer Tour

Travel between destinations and visit sights along the way. Stop to visit the medieval fortress of Monteriggioni before spending leisure time in the hill-town of...

7 hours Hotel pickup offered Free Cancellation

5.0 (9)

from
$902

Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

Enjoy a day trip to three of Tuscany’s most iconic destinations: Montalcino, home of the famous Brunello wine; Pienza, renowned for its Pecorino cheese; and …More

4.8 (8)

Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

Enjoy a day trip to three of Tuscany’s most iconic destinations: Montalcino, home of the famous Brunello wine; Pienza, renowned for its Pecorino cheese; and...

10 to 11 hours Free Cancellation

4.8 (8)

from
$261

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

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
$251

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

Private Tour: Guided Hike in Tuscany with Transport from Siena

Explore Tuscany's picturesque rolling hills on a private, full-day hiking and sight-seeing tour with transport from Siena. Enjoy a scenic, full-day adventure with your expert …More

5.0 (7)

Private Tour: Guided Hike in Tuscany with Transport from Siena

Explore Tuscany's picturesque rolling hills on a private, full-day hiking and sight-seeing tour with transport from Siena. Enjoy a scenic, full-day adventure with your expert...

7 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$217

Fascinating walk to discover Siena, the most famous monuments and the least known and most precious places. We will walk through alleys and medieval streets, …More

5.0 (7)

Siena private guided tour for families

Fascinating walk to discover Siena, the most famous monuments and the least known and most precious places. We will walk through alleys and medieval streets,...

2 hours Free Cancellation

5.0 (7)

from
$264

Take a chance to discover Siena, a jewel of the Middle Ages set in the Tuscan hills, full of history and culture. Accompanied by a …More

5.0 (6)

Private Siena walking tour

Take a chance to discover Siena, a jewel of the Middle Ages set in the Tuscan hills, full of history and culture. Accompanied by a...

3 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$57

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

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
$259

Capture your memories of Siena on camera with this private photo shoot in the heart of the city. The experience is led by a professional …More

5.0 (4)

Private Photo Shoot in Siena

Capture your memories of Siena on camera with this private photo shoot in the heart of the city. The experience is led by a professional...

1 hour 30 minutes Free Cancellation

5.0 (4)

from
$360

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

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)

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

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
$272

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

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
$274