Top Day Trips from Tuscany (Updated November 2026)

Tuscany, Italy
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
$259
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
$237
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
$124
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
$55
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 …More

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
$270
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
$301
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
$351
PISA HALF-DAY: from Florence by minivan with Leaning Tower ticket

Discover the magic of Pisa city center by travelling in a comfortable minivan from Florence. Stand under the notorious Leaning Tower of Pisa and stroll …More

Discover the magic of Pisa city center by travelling in a comfortable minivan from Florence. Stand under the notorious Leaning Tower of Pisa and stroll...

5 hours Free Cancellation
4.8 (5)
from
$130
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
$1,010
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
$497
Best of Tuscany Private Tour: Siena, San Gimignano, Monteriggioni

Experience the best of Tuscany and its gorgeous hilltop towns in one day! Currently due to Covid-19 regulations, this tour can only be run as …More

Experience the best of Tuscany and its gorgeous hilltop towns in one day! Currently due to Covid-19 regulations, this tour can only be run as...

9 hours
5.0 (7)
from
$1,522
From Pisa: Private San Gimignano & Chianti Tour with Lunch

A private day from the Pisa area through the Tuscan hills, with a farm lunch and two wine tastings. • Pickup at your hotel or …More

A private day from the Pisa area through the Tuscan hills, with a farm lunch and two wine tastings. • Pickup at your hotel or...

8 hours Hotel pickup offered Free Cancellation
5.0 (2)
from
$282
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
$275
Private Cinque Terre Day Trip from Florence WITH or WITHOUT Pisa

With the opportunity to hike between the five towns, our Cinque Terre private tour lets you experience the breathtaking scenery and atmosphere of this well-known …More

With the opportunity to hike between the five towns, our Cinque Terre private tour lets you experience the breathtaking scenery and atmosphere of this well-known...

11 hours Hotel pickup offered Free Cancellation
5.0 (1)
from
$643
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
$1,035
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
$845
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
$277
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
$226
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
$1,240
Wine Tour in the Countryside of Lucca with Lunch - with Minivan

This tour is including a car at your disposal during the tour, transfer to a beautiful winery in Montecarlo where you can taste 4 different …More

This tour is including a car at your disposal during the tour, transfer to a beautiful winery in Montecarlo where you can taste 4 different...

5 hours Hotel pickup offered Free Cancellation
5.0 (11)
from
$192
Tour of San Gimignano and Private Wine Experience in Chianti

Visit one of the most famous Italian wine areas, San Gimignano, with your private group followed by a wine tasting at a family-owned winery in …More

Visit one of the most famous Italian wine areas, San Gimignano, with your private group followed by a wine tasting at a family-owned winery in...

5 hours Hotel pickup offered Free Cancellation
5.0 (2)
from
$220
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