A private tour of Tuscany is the best bang for your buck when your time is limited and you want to experience as much as you can of everything under the Tuscan sun.  I had driven through the Tuscan countryside on several occasions  with some  friends and a Michelin Guide; although the experience was unforgettable we didn’t see nearly as much as I got to see on my private guided tour.

On my last trip to Italy I knew that our time was limited to a day-trip from Florence for the wine tasting and sightseeing that my friends had requested.  Taking a train was not an option since most of the small hillside towns are not serviced by the railroads.  I seriously considered renting a car, but my biggest fear about driving in Italy isn’t driving in Italy, but parking.  Quite honestly, I’m afraid to park in downtown L.A.  because once you’ve had your car towed, twice shy, as they say, so if it were possible to even find a parking spot in one of those tiny villages in Tuscany, I wouldn’t be able to enjoy myself while in a panic over what, if anything, I’d find on my return, so scratch the stupid car rental idea.  At this point I knew I would have to bite the bullet and take a tour, but after some research I found a private guide, which turned the plan into something to look forward to with excitement rather than dread.  (Sort of like a first class flight vs. coach.) Only those of you who have been on a packed mini-bus with a group comprised of Russians, Brazilians, Brits, and Japanese, with an Italian guide who speaks in English, Spanish, and French (all of which sound the same, none of which is comprehensible) are able to understand how willing I was to spend just a teensy bit more money in order to customize my own tour.

I found Alessandro Cammilli on TripAdvisor, ranked #1 of “Activities in Florence.”  His reviews were glowing so I contacted him with my dates.  Alessandro is a busy guy. We were lucky to secure a day with him and that was only because his hometown football team, La Fiorentina, did not qualify for some national thing (I didn’t ask for details) which freed his schedule up for us.  (He is obviously an Italian man with his priorities in order.)  His website has suggested itineraries, all of which sounded tempting, but we settled on a tour of towns in Northern Tuscany, which I was able to customize however I liked.

We were picked up at our hotel in Florence at 9 am, and drove in his comfortable, clean car that seats up to six passengers.  Our first stop was Piazzale Michelangelo, the famous lookout point above the city of Florence.  From there we drove to our first winery, Castello Vicchiomaggio, in Greve in Chianti.  Along the way Alessandro told us all about the wine industry in Italy while we admired the landscape from both sides of the car.  After the wine tasting at the castle, (how often can you say that?) he took us to the town of Greve in Chianti for a salami, cheese, and honey tasting.  We shopped for linens and cheese while there, then went on to visit three more wineries with lunch in between.

All of our stops were at places where they knew Alessandro, and I know what you’re thinking, but I must tell you that the price of our tour included all the wine, cheese, salami, and balsamic vinegar tasting, and it was nice to be treated as a VIP guest by all of the owners of the wineries.  (We noticed that other guests who had just dropped in were charged a fee.)  After every stop Alessandro would give us choices as to what we wanted to do next: go to another winery, get something to eat, visit a town, shop – our wish was his command.

After lunch we sobered up and concentrated on sightseeing.  There are probably close to a hundred hillside towns in Tuscany, each with its own unique characteristics and more beautiful than the last one.  Alessandro would park at the entrance to the town and show us to the main street that goes from one end to the next, we would take our time visiting churches and shops, and find him waiting for us at the other side, ready to take us to our next stop.  Our final town was San Gimignano by my special request, but I skipped the Museum of Torture and bought a purse instead.

The nap in the car on the way back to Florence was worth the teensy bit extra we paid for the privilege of not having to sit next to a woman yelling at her husband in Russian.  Here’s the link to Alessandro’s website, and tell him I promised you a discount.

Wineries:

Castello Vicchiomaggio, Greve in Chianti
Montagliari e Castellina, Greve in Chianti
Castelvecchi, Radda in Chianti

Towns:

Greve in Chianti
Radda in Chianti
Castellina
San Gimignano