Living (with) abroad in Tuscany: Massi the driver—and photographer—a great choice to experience the rural beauty and character of Tuscany

Massi the Driver. All photos on this page are by Massi

Massimiliano Mori of Southern Tuscany is known to many as Massi the Driver because he is licensed to drive tourists to and from their destinations or take them on food and wine tours. While he not be an official tour guide per se, many of his customers consider him the best guide they’ve ever had, simply because he is so knowledgeable about the best places to take stunning scenic photos, eat lunch or dinner, or sample wine, oil and antipasto.

A misty morning in the Southern Tuscany

I’ve never actually met Massi, but I’ve seen some of his photos in a Facebook group of which we share membership, and since then we have become friends on Facebook. He has previously granted me permission to use some of his images in my blog posts, but he has so many stunning photos that I decided to dedicate an entire entry to him—simply because his photography deserves a wider audience. Look at the photos and see for yourself!

Sunset in the Crete Sinesi.

As far as his driving services, Massi is described as gracious, accommodating, attentive and knowledgeable. He lives in Asciano, the center of Crete Senesi, about 15 minutes from Siena. Crete Senesi literally means the clay of Siena, and a tourism site describes it thusly: “It is a singular region. Like an island: exuberant, uncompromising, where the sun really shines, the wind blows unhindered, the light is blinding, and one’s gaze can range ruthlessly everywhere, chasing distant horizons, magnificent lines, and unforgiving wastelands.”

Cartizze Hill.

Massi speaks English as well as Italian, and he provides transportation to and from airports, railway stations, bus stations, ports and moorings for cruise ships—basically anywhere one wants to go. Though he advertises himself as a driver, his customers know he is far more. He is familiar with stunning but little-known attractions in the region, including farms, factories, sagras, panoramic vistas and friendly and welcoming local characters. He will take photo enthusiasts out early in the morning or the late evening, when the light is best, and he knows all the most photogenic locations.

Chianti Shire.

I’ve stated before that the most memorable aspects of a trip to Italy are not just the sights but the people, and I’ve a feeling that Massi’s customers remember him fondly. If I were taking a trip to Southern Tuscany again, I think I’d just call Massi up and tell him to put together an agenda of his favorite cities. Take a look some of his many glowing reviews on Tripadvisor.

Castello di Brolio

Ashley F writes: “Massi built the tour around what we wanted to see and picked great locations that we would have never found on our own. We visited two wineries, had an espresso in a small town and enjoyed a huge cheese tasting of locally made pecorino. Massi was very knowledgeable about the region and taught us about wine production as we drove between stops.”

Grape vines in the fall.

John C. from Balmain, Australia, said: “Massi took us to four fantastic wineries, all of which were unique in their own way. We got a little out of hand and excited in how many bottles of wine we purchased, and Massi arranged for them to be sent home—he really went the extra mile! He was so friendly and informative and was obviously well respected by the winery operators.”

The famous Ponte Vecchio in Firenze.

Shane and Bev from Dartmouth, Canada, wrote: “We didn't have any set agenda and Massi was more than willing to help out but was also flexible to do whatever we wanted. He was professional, knowledgeable, and put us at ease immediately. He took us to a couple of great wineries and we got to see some views that we will never forget.”

Patterns in the sky.

Ciao Italy from San Antonio, Texas, wrote a rave review: “Massi is gifted at his profession. I say profession and not job because what he offers is far more than a driving service. He grew up in Tuscany, knows the winery profession first-hand, and appreciates/understands fine food/wine. He is always learning, networking, and improving his services. He takes trips to new locations in the off-season to build knowledge and contacts and expand his offerings.

Badia a Passignano.

“As for the driving portion, Italy is very particular on who may drive tourists, so his license as a driver is important. It allows him, for example, to drive through the pedestrian-packed streets of Siena and meet you in the historic walking zones. His skill as a driver is top-notch. He drove ambulances in the region in the past, so his knowledge of the area is excellent, and he is skilled at maneuvering and navigating his vehicle on the twisty narrow Tuscan roadways. His automobile was very comfortable, and the ride was always smooth and enjoyable. Massi understands the importance of details. He provided extras which made the trip more enjoyable, such as chilled drinking water in a cooler and delicious pastries from a local bakery.

Sundown at Cinque Terre.

“Massi was incredibly patient with customizing and planning the itinerary. Many of the Tuscan guides offer a take-it-or-leave-it tour. As a consequence, if you are hoping to visit a winery or site that isn’t part of the pre-conceived plan, you will miss the opportunity. Massi, however, was accommodating and flexible. If you don’t have a list of places you would like to go, he will schedule an amazing day for you. If you are like me, and tend to advance-plan and revise, Massi will work with you to craft an unforgettable trip.

“Massi has an impeccable sense of timing. I would invariably try to overschedule the day, hoping to fit in one more winery or site. Fortunately, he presciently and gently course corrected so that he made every appointment on time. Thanks to Massi, we never felt hurried, yet we managed to achieve all our important objectives.