Castiglion Fiorentino, Tuscany

Fun Nights in Castiglion Fiorentino

Explore the Cities and Towns of Tuscany

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Over 20 years of crafting exceptional journeys across Castiglion Fiorentino

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Every itinerary is thoughtfully crafted around your pace, from private dawn tours to intimate vineyard tastings.

Overview

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.  
 

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Castiglion Fiorentino

Stories That Stay With You

Here's what our guests share about their unforgettable journeys

“We're home now from the most amazing trip to Italy! I can't thank you enough for your efforts and coordination of what was without question the finest vacations I've been on to date.”
[Read More] Carol Carson
“I am a travel agent from Lebanon and have organized several group tours as well as individual tours of Italy with Italy Vacation Specialists. I highly recommend them as one of the very best tour operators in Italy to work with, given their professionalism and work ethic which I feel is second-to-none in the travel industry. All of the staff, the guides, the coaches and even the meals we enjoyed we”
[Read More] Nicole Haddad, Lebanese Travel Agent
“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 we were exploring your great country.”
[Read More] Leon and Michele
“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 on vacation to make sure things were going well. I plan on using them again soon for all my future bookings!”
[Read More] Tammy Joyce, All About Honeymoons
“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 flying to Rome where honestly 4 days is NOT enough. They keep saying to spend more time and we could not agree more! You need to spend more ti”
[Read More] Robin and Kumi Bruun, Tokyo Japan
“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 to drive ourselves. Having traveled with them many times and done business on several occasions, most definitely USE this company. They know”
[Read More] JoAnne Beaudoin, Retired Nurse
“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 wonderful. The staff were very friendly and helpful and made the first portion of our journey very stress free. They made us feel like we were p”
[Read More] Ron and Deb Crosby
“Jesse, There are no words to describe the fabulous time we had in Italy. Everything went as you promised. Absolutely no problems! The venues were fabulous. The guides were punctual and helpful. It couldn't have worked out better. You and your staff deserve high praise for the quality and efficiency of your work. BTW, Guiseppe was an absolute delight. We enjoyed his informative and effervescent per”
[Read More] Jo Ann West
“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 can best see the country and not fall into tourist traps. I have been on 4 trips with the IVS team, firstly when they did my first 2 trips f”
[Read More] Laura Chomiak, Travel Agent
“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 team took a huge burden off of me! I would like to start of by saying "THANK YOU" both for the amazing job you did on our trip. There was n”
[Read More] Ann Brownell, KHM Travel Group

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