Castiglion Fiorentino, Tuscany

Fun Nights in Castiglion Fiorentino

Overview

Discover Castiglion Fiorentino: Private Tours, Experiences & Custom Travel

Castiglion Fiorentino is a beautiful small town located in the Tuscany region in the province of Arezzo about a 10 minute drive from the very popular and touristic town of Cortona made famous and drawing many visitors after the novel Under the Tuscan Sun was published by author Fraces Mayes (see her bio on Wiki here).  Shortly after her film about Corton and her adventures in south-eastern Tuscany was made world-famous in the film "Under the Tuscan Sun" - Cortona 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 Cortona is how things still are in Castiglion Fiorentino and that's why we like it!

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

Map

Get your bearings before you go

Villas

Private homes with stories of their own

Apartments

A local address to call your own

Our Featured Properties

Stays we picked one by one

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.

Starting somewhere else? Tell us where, and we will arrange the car.

Plan my transfer

Quick Enquiry Form

Tell us about your dream trip and we'll craft the perfect itinerary for you.

Castiglion Fiorentino

In their words

Stories That Stay With You

Here's what our guests share about their unforgettable journeys

“I am a travel agent with All About Honeymoons and I would highly recommend Italy Vacation Specialists. Jessica was wonderful in helping us plan in a last minute anniversary vacation during high season without any issues. She even checked on our clients while o…”

Tammy Joyce, All About Honeymoons Read their story

“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

“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

“I have traveled to Italy 2x with the IVS for my own pleasure trips and 2x for business with IVS. These guys really pay attention and make your trip go like clockwork. Italy is nuts, just saying! There are so many rules and restrictions now, so we did not want…”

JoAnne Beaudoin, Retired Nurse Read their story

“As a travel agent, but also a traveler to Italy, thee is no other company I would recommend than the Italy Vacation Specialists. Not only do they really care about what they are doing, they also really know Italy and try to educate many people about ways they…”

Laura Chomiak, Travel Agent Read their story

“In September of 2018 I brought a group of 12 from Venice to Sicily and organized all of my services with the Italy Vacation Specialists. Being a travel agent and in the business, I know how complicated organizing travel arrangements can be in Italy and the IVS…”

Ann Brownell, KHM Travel Group Read their story

Plan it with us

For customized holidays and expert advice for travel in Italy and the Mediterranean, Get in touch with your travel agent or contact us via our.

  • Direct In Italy: +39 375 823 5314

  • Toll Free: 1-866-779-2565