Castiglion Fiorentino, Tuscany

Overview

Discover Castiglion Fiorentino: Private Tours, Experiences & Custom Travel

Castiglion Fiorentino is a beautiful small town located in the region in the province of Arezzo about a 10 minute drive from the very popular and touristic town of made famous and drawing many visitors after the novel Under the Tuscan Sun was published by author Fraces Mayes (see her bio on Wiki ). Shortly after her film about Corton and her adventures in south-eastern was made world-famous in the film "Under the Tuscan Sun" - and much of the surrounding area became world famous, all the while Castiglion Fiorentino an important and gorgeous neibouring town taking a back-seat and carrying on its normal and local simple yet refined Tuscan tradition so when coming to the area - expect a non-touristic approach, a local flavor and a down to earth people who are still curious and may be waving at you as your car drives by.

The way things use to be in is how things still are in Castiglion Fiorentino and that's why we like it!

Away from the crowds, a piece of that remains wonderfully authentic! This is Castiglion Fiorentino.

Plan Your Experience

Explore Castiglion Fiorentino

Our own photographs

Castiglion Fiorentino Through Our Eyes

Photographed during our own travels and research, these images follow the journey through Castiglion Fiorentino, from the first view of the landscape to the small details that give the place its character.

Castiglione Fiorentino Tuscany

Central Piazza at Castiglion Fiorentino - Tuscany - Italy

Tuscany

View Towards Castiglion Fiorentino by Tuscany Villa to Rent -

Countryside in and around Castiglion Fiorentino - Arrezzo Province

Map

Get your bearings before you go

Villas

Private homes with stories of their own

Italy,Tuscany,Castiglion Fiorentino

Villa

Villa Buccelletti: Great Option for Small Families, Couples of Group of Friends

4 Beds 4 Baths 10

BBQ +10 more

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Italy,Tuscany,Castiglion Fiorentino

Villa

Villa San Martino Cortona

3 Beds 5 Baths 12

BBQ +10 more

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Italy,Tuscany,Castiglion Fiorentino

Villa

Villa Stefano: Ideal Property for Artists, Families & Large Groups in Tuscany

7 Beds 6 Baths 16

BBQ +11 more

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Apartments

A local address to call your own

Villa Amore Toscana: Ideal Villa for Groups and Large Families with Gorgeous Private Pool apartment rental in Castiglion Fiorentino

Italy,Tuscany,Castiglion Fiorentino

Estate

Villa Amore Toscana: Ideal Villa for Groups and Large Families with Gorgeous Private Pool

16 Beds 16 Baths 26

BBQ +11 more

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Photo Gallery

Castiglion Fiorentino

Viareggio

Volterra

Arezzo

Bagno Vignoni

Barga

Carrara

Castiglion Fiorentino

Chianciano Terme

Chianti

Cortona

Elba Island

Fiesole

Florence

La Verna

Livorno

Lucca

Maremma

Montalcino

Montecatini

Montepulciano

Monteriggioni

Monticchiello

Pienza

Pietrasanta

Pisa

Porto Santo Stefano

San Gimignano

San Miniato

Saturnia

Siena

Terme di San Filippo

Val D'Orcia

Viareggio

Volterra

Our Featured Properties

Stays we picked one by one

Cottage Talluri featured rental property in Castiglion Fiorentino

Italy,Tuscany,Chianti,Castellina in Chianti

Estate

Cottage Talluri

2.5 Beds 5

Air Conditioning +9 more

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La Dimora del Gazebo featured rental property in Castiglion Fiorentino

Italy,Tuscany,Siena

Apartment

La Dimora del Gazebo

3 Beds 2 Baths 6

Air Conditioning +16 more

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Vista Collina featured rental property in Castiglion Fiorentino

Italy,Tuscany,Montepulciano

Apartment

Vista Collina

1 Beds 1 Baths 2

Air Conditioning +8 more

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Italy,Tuscany,Chianti

Villa

Villa Castrum

5-7 Beds 10-14

Air Conditioning +4 more

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Italy,Tuscany,Florence,Montaione

Villa

Villa in Iano with breathtaking view

4 Beds 9

Air Conditioning +13 more

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Italy,Tuscany,Florence

Villa

Villa Fiori d'Arte

8 Beds 8 Baths 16-18

Air Conditioning +13 more

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La Dimora Regale 1 featured rental property in Castiglion Fiorentino

Italy,Tuscany,Arrezzo

Villa

La Dimora Regale 1

1 Beds 1 Baths 2

Air Conditioning +11 more

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Cottage Fienile featured rental property in Castiglion Fiorentino

Italy,Tuscany,Siena (SI),Castellina in Chianti

Estate

Cottage Fienile

Air Conditioning +10 more

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Casa Divina featured rental property in Castiglion Fiorentino

Italy,Tuscany,Montepulciano

Apartment

Casa Divina

2 Beds 2 Baths 4

Air Conditioning +9 more

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Duetto Classico featured rental property in Castiglion Fiorentino

Italy,Tuscany,Montepulciano

Apartment

Duetto Classico

2 Beds 1 Baths 4

Air Conditioning +8 more

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Italy,Tuscany,Grosseto,Montemerano

Villa

Bella Villa di Campagna

11 Beds 12 Baths 26

Air Conditioning +17 more

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Wonders Room featured rental property in Castiglion Fiorentino

Italy,Tuscany,Montepulciano

Apartment

Wonders Room

1 Beds 1 Baths 2

Air Conditioning +6 more

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Getting here

The Road to Castiglion Fiorentino

Most of our guests arrive by private car, with a driver who knows these roads and where it is worth stopping along the way. These are the journeys we arrange most often.

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Arezzo - Town Centre, Etruscan City, Tuscany Italy

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In their words

Stories That Stay With You

Here's what our guests share about their unforgettable journeys

“Dear Guiseppe and Jesse, We just returned from our most wonderful vacation to Italy and wanted to first thank you for putting together such a wonderful trip, and second to provide some feedback for the future. Hotels 1. Hotel Sovestro in San Gimignano was wond…”
Ron and Deb Crosby Read their story

“This company really knows their stuff and recommended our family to stay longer in each location. We didn't listen to them, but wished we had in every single place we went. They recommended Sestri Levante over the Cinque Terre which was our favourite destinati…”
Sean & Veet Chapman, CGA Read their story

“Jesse & Giuseppe, Sandy and I have been looking through my slides of our trip to Southern Italy. We had such a good time with you and Giuseppe that we wanted to let you know again. You were the best guides ever”
Bob & Sandy Read their story

“The trip was great; we appreciate all the hard work you and your team invested to make our experience a once in a lifetime trip. We appreciate all the attention to the details, in particular Giuseppe spending the time and the focus with us on the road and as w…”
Leon and Michele Read their story

“I went to high school with the owner of the company who organized my honeymoon for myself and my now wife from Tokyo. We spent three short weeks seeing Piedmont and experiencing wine paradise there, then heading to Nice in France with our private driver and fl…”
Robin and Kumi Bruun, Tokyo Japan Read their story

“My husband and I just took a two week trip to Italy that was planned for us by Eleanor Kinchin-Smith. It was a fantastic trip and we could not have been more thrilled. We worked together with Ele to let her know about our interests and our style of travel. She…”
Emily and David Davison Read their story