Top Siena Tours & Sightseeing

Q: Which Siena Tours & Sightseeing have Instant Confirmation?

Siena Tours & Sightseeing with Instant Confirmation include: Siena: A Wine Tour and Tasting Experience Hot Air Balloon Flight Over Tuscany from Siena Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch Italian Opera in Siena Experience 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 →

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

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

Siena to Rome: Orvieto and Montepulciano Transfer Tour

Have a private vehicle pick you up from your Siena accommodation and enjoy a full-day transfer to Rome in the company of your driver guide with …More

5.0 (4)

Siena to Rome: Orvieto and Montepulciano Transfer Tour

Have a private vehicle pick you up from your Siena accommodation and enjoy a full-day transfer to Rome in the company of your driver guide with...

7 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$1,130

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

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

A private wine day from Siena to the Val d'Orcia, home of two of the greatest Italian red wines: Vino Nobile di Montepulciano and Brunello …More

5.0 (3)

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

A private wine day from Siena to the Val d'Orcia, home of two of the greatest Italian red wines: Vino Nobile di Montepulciano and Brunello...

9 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$261

Brunello di Montalcino wine experience with a sommelier

This private tour is designed to offer an authentic experience with maximum comfort and local insight. It starts directly from your hotel in a fully …More

5.0 (3)

Brunello di Montalcino wine experience with a sommelier

This private tour is designed to offer an authentic experience with maximum comfort and local insight. It starts directly from your hotel in a fully...

5 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$228

Any season has its own truffles, the black you can find almost all year round and the celebrated white ones, which season starts in October. …More

5.0 (3)

Private Truffle Hunt in Tuscany

Any season has its own truffles, the black you can find almost all year round and the celebrated white ones, which season starts in October....

4 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$241

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

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
$294

Enjoy Siena with a professional guide who will let you discover the beauties of this UNESCO world heritage listed city. The itinerary will include the …More

5.0 (2)

Half-day Private Walking Tour of Siena

Enjoy Siena with a professional guide who will let you discover the beauties of this UNESCO world heritage listed city. The itinerary will include the...

3 hours Free Cancellation

5.0 (2)

from
$425

Suvereto Wine Experience PRIVATE TOUR from SIENA

* An UNIQUE off-the-beaten-path tour. Amazing locations, stunning masterpieces of architecture designed by Renzo Piano and Mario Botta.... * A family-run boutique winery experiences * …More

5.0 (2)

Suvereto Wine Experience PRIVATE TOUR from SIENA

* An UNIQUE off-the-beaten-path tour. Amazing locations, stunning masterpieces of architecture designed by Renzo Piano and Mario Botta.... * A family-run boutique winery experiences *...

10 hours Hotel pickup offered

5.0 (2)

from
$276

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

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
$340

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)