Top things to do in Siena in Summer (Updated November 2026)

Siena, Italy
Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch

Our driver guide will collect you at the designated meeting point, setting off toward Montalcino. Start this full-day tour with a lesser-known boutique vineyard with …More

Our driver guide will collect you at the designated meeting point, setting off toward Montalcino. Start this full-day tour with a lesser-known boutique vineyard with...

8 hours Hotel pickup offered Free Cancellation
4.9 (109)
from
$261
Siena Walking Tour with Audio and Written Guide by a local

If you're looking for a fun and curious way to visit Siena, you've come to the right place! With this digital guide created with the …More

If you're looking for a fun and curious way to visit Siena, you've come to the right place! With this digital guide created with the...

4 to 5 hours Free Cancellation
4.4 (42)
from
$6
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

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
Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch

To fully experience la "Bella vita", you need to get out of the city. Taste the local wines & tour the cellars of select family-run, …More

To fully experience la "Bella vita", you need to get out of the city. Taste the local wines & tour the cellars of select family-run,...

6 to 8 hours Hotel pickup offered Free Cancellation
4.9 (77)
from
$284
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

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
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

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
$308
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

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
Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Taste Tuscany's delicious cheeses and the great Brunello di Montalcino red wines on a full-day private guided tour. See the beautiful Val d'Orcia and receive …More

Taste Tuscany's delicious cheeses and the great Brunello di Montalcino red wines on a full-day private guided tour. See the beautiful Val d'Orcia and receive...

8 hours Hotel pickup offered Free Cancellation
5.0 (41)
from
$795
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

Likely to Sell Out
Likely to Sell Out

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
The Most Delicious Private Food Tour of Siena: 10 Tastings

Fall in love with the flavorful Tuscan cuisine on this private food tour in Siena! Enjoy a selection of 10 food and drink tastings hand-picked …More

Fall in love with the flavorful Tuscan cuisine on this private food tour in Siena! Enjoy a selection of 10 food and drink tastings hand-picked...

3 hours Free Cancellation
5.0 (11)
from
$111
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

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
$137
Chianti Half Day Wine Tasting Tour from Siena

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in …More

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in...

5 hours Free Cancellation
4.8 (10)
from
$56
Cities, Cheese and Wine Tour in Pienza & Montepulciano

Pienza and  Montepulciano Wine Tour - Experiences 1-day exciting trip in Valdorcia Join us for a firsthand look into the wine cellars producing world-class reds, including …More

Pienza and  Montepulciano Wine Tour - Experiences 1-day exciting trip in Valdorcia Join us for a firsthand look into the wine cellars producing world-class reds, including...

6 to 8 hours Hotel pickup offered Free Cancellation
4.9 (25)
from
$330
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

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
$258
From Siena: Private Brunello & Nobile Wine Tour with Lunch

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

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
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

* 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
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

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
Private wine tour of Chianti

Your driver will come to your accommodation around 930 to whisk you off to your first wine tour and tasting. During the day we will …More

Your driver will come to your accommodation around 930 to whisk you off to your first wine tour and tasting. During the day we will...

6 to 8 hours Hotel pickup offered Free Cancellation
4.6 (10)
from
$326
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 …More

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
$358
Siena Highlights Private Walking Tour With A Guide (Private Tour)

Commence your journey at the iconic Piazza del Campo, immersing yourself in the vibrant atmosphere of Siena's renowned square. Delve into the city's history at …More

Commence your journey at the iconic Piazza del Campo, immersing yourself in the vibrant atmosphere of Siena's renowned square. Delve into the city's history at...

3 hours Free Cancellation
4.6 (40)
from
$31
Pisa, San Gimignano & Chianti Day Trip with Lunch & Wine Tasting

Depart from Siena and enjoy a full-day tour to Pisa, San Gimignano, and Chianti. Savor a traditional lunch at a Chianti winery with antipasto, fresh …More

Depart from Siena and enjoy a full-day tour to Pisa, San Gimignano, and Chianti. Savor a traditional lunch at a Chianti winery with antipasto, fresh...

11 hours Free Cancellation
4.5 (6)
from
$90
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