Top Day Trips from Tuscany (Updated November 2026)

Tuscany, Italy
Castles & Chianti Wine Experience– Small Group from San Gimignano

Experience the beauty of the Chianti region and immerse yourself in the unforgettable Tuscan countryside. Discover the world-famous Chianti wine, known for its ruby-red color …More

Experience the beauty of the Chianti region and immerse yourself in the unforgettable Tuscan countryside. Discover the world-famous Chianti wine, known for its ruby-red color...

7 hours Free Cancellation
4.3 (15)
from
$96
Semi-Private Truffle Hunting & lunch @ Winery, San Gimignano

After a one-hour comfortable drive from Florence to the Chianti region, you will meet with our professional truffle hunter. You will enjoy hiking through vineyards …More

After a one-hour comfortable drive from Florence to the Chianti region, you will meet with our professional truffle hunter. You will enjoy hiking through vineyards...

7 to 8 hours Free Cancellation
5.0 (27)
from
$546
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
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

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
Private Bike Tour & Chianti Wine Tasting in Tuscany

A full-day cycling tour from Florence into the enchanting Chianti region promises a delightful escape into the Tuscan countryside. Pedal along serene country roads surrounded …More

A full-day cycling tour from Florence into the enchanting Chianti region promises a delightful escape into the Tuscan countryside. Pedal along serene country roads surrounded...

7 to 8 hours Free Cancellation
5.0 (26)
from
$238
Private Half day Tour in Chianti, San Gimignano with wine tasting

Let us guide you through the medieval and legendary towers of San Gimignano. In the heart of Chianti, treat yourself to a break among centuries-old …More

Let us guide you through the medieval and legendary towers of San Gimignano. In the heart of Chianti, treat yourself to a break among centuries-old...

5 hours Hotel pickup offered Free Cancellation
5.0 (28)
from
$126
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
From Florence to Siena - San Gimignano & Pisa by private minivan

The tour starts with a ride by air-conditioned minivan and an English speaking driver from Florence to Siena.  First Stop at Piazzale Michelangelo for a …More

The tour starts with a ride by air-conditioned minivan and an English speaking driver from Florence to Siena.  First Stop at Piazzale Michelangelo for a...

10 hours Free Cancellation
4.6 (7)
from
$202
Private Minivan Tour to Siena and San Gimignano from Florence

During this private open-air tour in a comfortable minivan, you will explore the breathtaking towns of Siena, Monteriggioni, and San Gimignano. All are symbols of …More

During this private open-air tour in a comfortable minivan, you will explore the breathtaking towns of Siena, Monteriggioni, and San Gimignano. All are symbols of...

8 hours Hotel pickup offered Free Cancellation
4.4 (9)
from
$175
Private Chianti Winery Tour from Livorno with pick up and drop off

Once you reach Chianti Classico from Livorno in your cruise, enjoy this private tour of Chianti Classico. Take this opportunity and visit one of the most beautiful …More

Likely to Sell Out
Likely to Sell Out

Once you reach Chianti Classico from Livorno in your cruise, enjoy this private tour of Chianti Classico. Take this opportunity and visit one of the most beautiful...

8 hours
4.0 (1)
from
$305
Full Day Private Guided Tour to Assisi and Cortona from Florence

This excursion to Assisi and Cortona will bring you to discover two of the most beautiful cities in central Italy. The tour starts from your …More

This excursion to Assisi and Cortona will bring you to discover two of the most beautiful cities in central Italy. The tour starts from your...

10 hours Hotel pickup offered Free Cancellation
5.0 (4)
from
$157
Chianti Classico E-bike Tour

Our E-bike tour will lead you through the most famous wine area in Tuscany: Chianti Classico. You will ride amongst Sangiovese vineyards and olive groves …More

Our E-bike tour will lead you through the most famous wine area in Tuscany: Chianti Classico. You will ride amongst Sangiovese vineyards and olive groves...

8 hours Free Cancellation
5.0 (9)
from
$356
Pisa and San Gimignano Tour from Florence

Enjoy a day visiting Pisa, famous for the Leaning Tower and San Gimignano know as the "Manhattan of the Middle Ages". Incredible landscapes, history and …More

Enjoy a day visiting Pisa, famous for the Leaning Tower and San Gimignano know as the "Manhattan of the Middle Ages". Incredible landscapes, history and...

8 to 9 hours Hotel pickup offered Free Cancellation
4.9 (10)
from
$1,022
Tarot Garden and Maremma Park

Intact, unspoiled nature in the Maremma Park with a carriage ride of about an hour or, depending on the availability of the Park Guides or …More

Intact, unspoiled nature in the Maremma Park with a carriage ride of about an hour or, depending on the availability of the Park Guides or...

6 to 7 hours Free Cancellation
4.8 (18)
from
$499
Private Grape stomping in Chianti from Florence

Harvest has always been a time of celebration in the countryside: after months of hard work, the ripening of the grapes marks the beginning of …More

Harvest has always been a time of celebration in the countryside: after months of hard work, the ripening of the grapes marks the beginning of...

5 to 6 hours Hotel pickup offered Free Cancellation
5.0 (12)
from
$278
Pisa and Lucca Tour from Florence

EXPLORE PISA AND LUCCA WITH LIMOSERVICEINITALY! This is a great opportunity to visit Pisa and Lucca on a private tour with the possibility to add …More

EXPLORE PISA AND LUCCA WITH LIMOSERVICEINITALY! This is a great opportunity to visit Pisa and Lucca on a private tour with the possibility to add...

8 hours Hotel pickup offered Free Cancellation
5.0 (12)
from
$1,048
Excellent Wine experience in English, Español, Purtuguês

On this tour we will visit two of the most beautiful cities in Tuscany, important both for art and culture and of considerable historical importance. …More

On this tour we will visit two of the most beautiful cities in Tuscany, important both for art and culture and of considerable historical importance....

8 hours Hotel pickup offered
5.0 (12)
from
$861
Chianti from Florence:PRIVATE Wine, Olive Oil Tasting in the Tuscan countryside

“If you truly want to experience the Chianti region, this is the tour you’ve been looking for!” The Chianti region is celebrated worldwide for its …More

“If you truly want to experience the Chianti region, this is the tour you’ve been looking for!” The Chianti region is celebrated worldwide for its...

6 to 7 hours Hotel pickup offered Free Cancellation
5.0 (4)
from
$279
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

* 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
Private Classic Wine Tour in Chianti from Florence

Chianti Classico is more than just wine—it’s a way of life. On this tour, you will discover the passion, history, and unique terroir that make …More

Chianti Classico is more than just wine—it’s a way of life. On this tour, you will discover the passion, history, and unique terroir that make...

7 hours Hotel pickup offered Free Cancellation
5.0 (4)
from
$300
Pisa and Florence Private Tour with Wine Tasting

Discover the Essence of Tuscany: Pisa, Florence & Chianti Wine Experience Immerse yourself in the timeless beauty of Pisa and Florence—two of Tuscany’s most iconic …More

Discover the Essence of Tuscany: Pisa, Florence & Chianti Wine Experience Immerse yourself in the timeless beauty of Pisa and Florence—two of Tuscany’s most iconic...

9 hours
4.9 (10)
from
$1,255
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