Italy Express: Tuscany Cities and Landscapes

5 days • 4 nights
4.7
Thu, 10 Jul 2025 Mon, 14 Jul 2025
Planned
Total
$1,249
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Book your spot with a $104 deposit
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50%
nature
Nature and adventure
50%
20%
relax
Relax
20%
40%
history
Monuments and history
40%
20%
culture
City and cultures
20%
0%
party
Party and nightlife
0%
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Art & Culture
Tuscany 5 days
Thu, 10 Jul 2025 Mon, 14 Jul 2025
Planned

$1,249
Book your spot with a $104 deposit
Pay the outstanding balance of $ 1,145 by 10 Jun
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The deposit option is only available if you book this tour before 10 Jun.
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What's included

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Frequently asked questions

Itinerary

day 1

Welcome to Italy

culture
100 %
Check-in
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Round trip flights are not included in the package, so you can choose from where and when you want to fly. This is to give you maximum freedom of choice!

Check-in at the hotel in Florence and meet the rest of your group! Let's kickstart our adventure in Tuscany by taking a nice walk to find a fantastic local restaurant where we can toast and grab some dinner.

Included: overnight stay

Not included: meals and drinks

day 2

Chianti hills, Pienza and Siena

nature
70 %
history
30 %
culture
29 %
Chianti Landscapes
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Today we head towards the stunning Chianti region. The landscapes are postcard-like and, after stopping ever-so-often to take pictures, we will reach a local winery and enjoy a special local wine tasting experience. We will also discover some of the secrets to the winemaking processes. Afterwards, we will set off again to visit some of the unique and historic villages such as Greve and Castellina in Chianti. We then head to Pienza, famous for its pecorino cheese. - ready to taste another Italian masterpiece? In the evening we reach Siena where we will spend the night.

Included: overnight stay, car rental, local wine tasting experience

Money pot: fuel, tolls, and local entrance tickets

Not included: meals and drinks

day 3

Siena, San Giminiano and Pisa

nature
20 %
history
50 %
culture
50 %
Siena and San Giminiano

Good morning Siena, a city where we will explore it's medieval streets, Torre del Mangia, the Cathedral and the famous Piazza del Campo. After dedicating a good part of the morning to wandering around the city, we head to San Giminiano and Monteriggioni, two well-preserved medieval villages in which we lose ourselves among food tastings and unique landscapes. From Piazza della Cisterna we will climb to the top of Torre Grossa to witness a unique viewpoint.

Road to Florence via Pisa
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After a typical Italian lunch and some sing along in the car, we will finally reach the sea for a short stop in the city of Pisa; famously known for the Leaning Tower and the Campo dei Miracoli, a square rich in history and monuments such as the Pisa Cathedral, the Baptistery and the Camposanto cemetery. This will be a short but intense stop before returning to Florence, ready to make the most of our last full day!

Included: overnight stay, car rental and entrance to Torre Grossa in San Gimignano

Money pot: fuel, tolls, and local entrance tickets

Not included: meals and drinks

day 4

Exploring Florence

history
50 %
culture
50 %
party
29 %
Duomo Cathedral and Uffizi Gallery

We dedicate our last full day in this beautiful country to Florence, a city of Renaissance full of timeless charm and beauty. We will explore the Piazza del Duomo and its Cathedral built by Brunelleschi, to then reach Piazza della Signoria, the historic seat of the city municipality and gateway to entrance of the Uffizi Gallery. Are you ready to indulge in some art and culture?

Pitti, Ponte Vecchio and Boboli Gardens
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After an amazing few days, it is now our last afternoon together in Italy. Let's walk through the historic streets of Florence and discover iconic spots such as Palazzo Vecchio and Palazzo Pitti, and the infamous Ponte Vecchio. The love and romance that Ponte Vecchio if unique, as is the walk along the Arno river which takes us directly to the last stop of the day, the Boboli Gardens. It will be here that we say goodbye to Florence, admiring a breathtaking sunset from the Boboli terrace and sharing one last drink with our new friends.

Included: overnight stay, entrance fee to the Duomo Cathedral

Money pot: Boboli Garden, Uffizi Gallery and other ticket admissions

Not included: meals and drinks

day 5

Goodbye Italy

culture
100 %
Check out and goodbye
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Time to say goodbye: see you all at the next WeRoad adventure!

End of services. The itinerary may undergo some variations that differ from what is stated above. These variations may not be predictable nor depend on WeRoad’s will, i.e. climate conditions, national holidays, strikes, etc.

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The travel coordinators

Our travel coordinators are chosen because they are people like you. Not only are they the best travel buddy you could hope for, but they're trained professionals guaranteed to show you a travel experience like never before