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Home/Destinations/Chianti/Tuscan Countryside

Tuscan Countryside Tours

Postcard Tuscany: tours wind through Chianti’s rolling countryside of vineyards, olive groves and cypress-lined roads, with stops for views and tastings. A feast for the eyes.

200 tours · prices per person, book with partner

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch
Florence
San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch
4.5(5,302)·11 hours
from$90/ person
via Viator
Half-Day Chianti Wine Tasting from Florence with Two Wineries
Florence
Half-Day Chianti Wine Tasting from Florence with Two Wineries
4.5(4,670)·5h 30min
from$63/ person
via Viator
Florence Vespa Tour: Tuscan Hills, Food and Chianti Wine
Florence
Florence Vespa Tour: Tuscan Hills, Food and Chianti Wine
4.8(4,354)·6 hours
from$149/ person
via Viator
Siena, San Gimignano and Chianti Wines Day Tour from Florence
Florence
Siena, San Gimignano and Chianti Wines Day Tour from Florence
4.7(3,520)·10h 30min
from$74/ person
via Viator
Half day Chianti Vineyard Escape from Florence with Wine Tastings
Florence
Half day Chianti Vineyard Escape from Florence with Wine Tastings
4.5(2,892)·5 hours
from$63/ person
via Viator
Florence Chianti Vespa Tour with Wine Tasting & Meal
Florence
Florence Chianti Vespa Tour with Wine Tasting & Meal
4.8(1,880)·6h 30min
from$119/ person
via Viator
Tuscany Bike Tours Through the Chianti Hills with Wine Tasting
Florence
Tuscany Bike Tours Through the Chianti Hills with Wine Tasting
4.9(1,316)·6 hours
from$137/ person
via Viator
From Florence: Chianti Wine Experience with Tastings & Views
Florence
From Florence: Chianti Wine Experience with Tastings & Views
4.4(855)·5h 30min
from$40/ person
via Viator
Tuscany Vespa Tours Through the Hills of Chianti
Florence
Tuscany Vespa Tours Through the Hills of Chianti
5.0(578)·6 hours
from$183/ person
via Viator
Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano
Florence
Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano
4.8(345)·9 hours
from$223/ person
via Viator
Wine Experience In Chianti Hills from Florence
−14%
Florence
Wine Experience In Chianti Hills from Florence
4.6(242)·5 hours
from$38$45/ person
via Viator
Chianti Wine Tour with Tastings Semi-Private Experience
Florence
Chianti Wine Tour with Tastings Semi-Private Experience
4.9(220)·7 hours
from$213/ person
via Viator
Chianti Wine Tastings Day Trip at Sunset from Florence
Florence
Chianti Wine Tastings Day Trip at Sunset from Florence
4.5(195)·5 hours
from$148/ person
via Viator
Chianti Half-day Wine Tour in the Tuscan's Hills from Pisa
Pisa
Chianti Half-day Wine Tour in the Tuscan's Hills from Pisa
4.9(137)·4–5 hours
from$102/ person
via Viator
Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area
Chianti
Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area
4.9(136)·2 hours
from$46/ person
via Viator
Greve in Chianti Wine Tasting and Winery Tour
Chianti
Greve in Chianti Wine Tasting and Winery Tour
4.7(127)·1h 30min
from$57/ person
via Viator
Chianti Wineries Tour, Medieval Villages, Lunch, Wine Tastings
Florence
Chianti Wineries Tour, Medieval Villages, Lunch, Wine Tastings
5.0(126)·8 hours
from$206/ person
via Viator
Chianti Hills E-Bike Tour with Tuscan Lunch & Two Wine Tastings
Florence
Chianti Hills E-Bike Tour with Tuscan Lunch & Two Wine Tastings
4.7(113)·6 hours
from$51/ person
via Viator
Montefioralle Winery - Tour and Wine Tasting in Chianti
Chianti
Montefioralle Winery - Tour and Wine Tasting in Chianti
4.2(103)·1h 15min
from$40/ person
via Viator
Siena walking tour with lunch & Chianti wine
Siena
Siena walking tour with lunch & Chianti wine
4.8(101)·2h 30min
from$97/ person
via Viator
Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour
Chianti
Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour
5.0(87)·9 hours
from$525/ person
via Viator
Small-Group Chianti Trip with Wine Tasting from Siena
Siena
Small-Group Chianti Trip with Wine Tasting from Siena
5.0(83)·8 hours
from$217/ person
via Viator
Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano
Florence
Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano
4.8(80)·6 hours
from$80/ person
via Viator
Siena: Chianti Sunset Tour with Dinner & Wine Tasting
Siena
Siena: Chianti Sunset Tour with Dinner & Wine Tasting
5.0(58)·3 hours
from$109/ person
via Viator
Exclusive Winery Tour with Tasting and Dinner in Chianti vineyard
Florence
Exclusive Winery Tour with Tasting and Dinner in Chianti vineyard
4.6(58)·6h 30min
from$137/ person
via Viator
Florence: Private Half-Day Chianti Tour and Wine Tasting Optional
Florence
Florence: Private Half-Day Chianti Tour and Wine Tasting Optional
4.6(51)·5 hours
from$360/ person
via Viator
E-bike Chianti Classico Tuscany Tour with Wine and Lunch at Farm
Florence
E-bike Chianti Classico Tuscany Tour with Wine and Lunch at Farm
5.0(49)·7 hours
from$182/ person
via Viator
Organic Wine Tour&Tasting overlooking Chianti Classico Vineyards
San Gimignano
Organic Wine Tour&Tasting overlooking Chianti Classico Vineyards
4.8(37)·1h 15min
from$40/ person
via Viator
Chianti Wine Tour - Private Wine experience in Tuscany Countryside
Florence
Chianti Wine Tour - Private Wine experience in Tuscany Countryside
5.0(29)·8 hours
from$721/ person
via Viator
Half Day Escape to Chianti: Taste the Heart of Tuscany
Florence
Half Day Escape to Chianti: Taste the Heart of Tuscany
4.8(16)·6 hours
from$56/ person
via Viator
Siena: Chianti Wine Tour with Wine Tasting and Lunch
Siena
Siena: Chianti Wine Tour with Wine Tasting and Lunch
5.0(14)·3 hours
from$86/ person
via Viator
Chianti Wine Tour for Small Groups: 3 Family Wineries & Lunch
Florence
Chianti Wine Tour for Small Groups: 3 Family Wineries & Lunch
5.0(13)·8 hours
from$269/ person
via Viator
E-bike Tuscany and Chianti Self-Guided Tour with Vineyard Visit
Florence
E-bike Tuscany and Chianti Self-Guided Tour with Vineyard Visit
4.8(12)·6–7 hours
from$29/ person
via Viator
Private Chianti Countryside Vespa Tour from Florence
Florence
Private Chianti Countryside Vespa Tour from Florence
4.7(12)·5 hours
from$456/ person
via Viator
Chianti Half Day Wine Tasting Tour from Siena
Siena
Chianti Half Day Wine Tasting Tour from Siena
4.5(11)·5 hours
from$56/ person
via Viator
Chianti and Tuscany Hills Vespa Tour with Lunch and Wine Tasting
Florence
Chianti and Tuscany Hills Vespa Tour with Lunch and Wine Tasting
4.5(11)·6 hours
from$80/ person
via Viator
From Florence: Chianti Wine Tour with Tastings & San Gimignano
Florence
From Florence: Chianti Wine Tour with Tastings & San Gimignano
4.6(10)·5h 30min
from$63/ person
via Viator
Special Chianti Afternoon Wine Tour from Florence
Florence
Special Chianti Afternoon Wine Tour from Florence
3.4(8)·5h 30min
from$108/ person
via Viator
San Gimignano, Chianti and Montalcino Tour through Tuscan wine
Siena
San Gimignano, Chianti and Montalcino Tour through Tuscan wine
4.8(8)·11 hours
from$160/ person
via Viator
Exclusive lunch, Winery tour, Organic wines in Chianti Classico
Florence
Exclusive lunch, Winery tour, Organic wines in Chianti Classico
5.0(8)·2–3 hours
from$126/ person
via Viator
From Florence Chianti Wine Tour with Tastings Half Day
Florence
From Florence Chianti Wine Tour with Tastings Half Day
4.7(6)·5h 30min
from$58/ person
via Viator
HALF-DAY Tour to Chianti Wine Region: CHIANTI COLORS & FLAVORS
Florence
HALF-DAY Tour to Chianti Wine Region: CHIANTI COLORS & FLAVORS
3.8(4)·5h 15min
from$135/ person
via Viator
From Florence: Chianti Half-Day Wine Tour with Tasting
Florence
From Florence: Chianti Half-Day Wine Tour with Tasting
4.3(3)·5h 30min
from$56/ person
via Viator
Wine Tour of two Chianti wine estates on the hills of Florence
Florence
Wine Tour of two Chianti wine estates on the hills of Florence
5.0(2)·5 hours
from$366/ person
via Viator
Florence: Chianti Wine Tour & San Gimignano with 2 Wineries
Florence
Florence: Chianti Wine Tour & San Gimignano with 2 Wineries
5.0(2)·5h 40min
from$69/ person
via Viator
Picnic in the countryside in the heart of Chianti
Florence
Picnic in the countryside in the heart of Chianti
5.0(1)·2 hours
from$40/ person
via Viator
Chianti Half Day Wine Tour with Tasting from Florence
Florence
Chianti Half Day Wine Tour with Tasting from Florence
5h 30min
from$64/ person
via Viator

Tuscan Countryside in Chianti — FAQ

What is the Chianti countryside like?
Rolling hills of vineyards and olive groves.
What can you do there?
Enjoy views, tastings and hilltop villages.
Are there scenic drives?
Yes — the vineyard-lined roads are a highlight.

More things to do in Chianti

From FlorenceWine TastingSiena & San GimignanoFood & Cooking