Once in a Lifetime: Rob & Kim Go VIP in Tuscany!


The world is fascinated by Italy’s most famous region, Tuscany. There are countless books written about a person’s first hand experience living amongst the Italian Cypress trees in the rolling vineyard covered fields of this great region. Probably the most famous area within Tuscany is the wine producing region of Chianti. Specifically, the Chianti Classico region is definitely one of the most visited. It offers a multitude of vineyards, hill top medieval villages and quaint farm houses that have been converted into restaurants, villas and hotels. Patrons rush to this area to create their own, ‘Under the Tuscan Sun’ experience.

Rob and I have explored this region many times before. We’ve rented a car, gotten lost, consequently found some really cool places as a result of getting lost and had some great experiences in the Tuscan hillside. But, none of these prior experiences compared with out recent trip to Tuscany’s wine epicenter, Chianti. In the past, we just grabbed a map and found our way. This time we decided to do something different. We contacted Bravo!, the premier travel concierge in Italy and inquired about possible tours. The wonderful thing about working with Bravo! is that they can tailor your day-trip to your wants and desires. We explained that we were looking for something different, off the beaten path.

Bravo! customized an amazing, exclusive VIP private tour of the rolling hills of Chianti, the medieval village of San Gimignano and lunch at a hidden Michelin Star rated Osteria and a tour of one of Chianti’s oldest and most interesting wineries.


In the morning our English speaking, well educated and personable tour guide and private driver Michael, picked us up at our hotel, JK Place. Immediately he began telling us what to expect during our day trip through the beautiful hills and winding roads of the Chianti region of Tuscany. Along the way, he spoke to us about the history of Tuscany, the Tuscan people and of course, about Italy’s most prized possession, vino! Keep in mind, this is not a rehearsed script that Michael is reading from. He had a deep love, appreciation and understanding of his culture, country and history that we hung on every single word that left his lips. It was one of the most fascinating conversations that we’ve ever had with a tour guide!

Once we arrived in the hill top village of San Gimignano, we were escorted to the front gate and set free to explore this medieval walled town. In other cities, such as Florence, most or all of their towers have been brought down due to wars, tragic accidents, or community projects. However, San Gimignano has managed to conserve fourteen towers which have become its international symbol. It is so much fun to get lost in the winding pedestrian streets of this village. The town contains four squares: Piazza della Cisterna, Piazza Duomo (where the Collegiata is located) Piazza Pecori, and Piazza delle Erbe. It is also worth a visit to the Museo Criminale Mediovale (The Museum of Medieval Torture) to see some of the town’s darkest moments in history.


After about an hour of touring inside the walls of San Gimignano. We went back to meet Michael at the car and headed off to Badia a Passignano to have lunch at Osteria di Passignano. This Michelin Star rated casual Osteria sits in the heart of a 215-hectare vineyard owned by the Antinori family and adjacent to a monastery that dates back to 395. The building which now houses Osteria di Passignano, as well as the Antinori wineshop called ‘La Bottega’, is an 18th century building near the abbey entrance.

When we drove up the private driveway to this massive monastery, we knew that this place was going to be amazing. Once inside the Osteria, we were promptly given a welcome glass of sparkling wine and a tasting ‘from the chef’. I have to say, when I put this small offering into my mouth, it was a religious experience. I quickly told our waiter how outstanding I thought this creative combination of polenta and other local ingredients was. He replied, “It can not be outstanding yet.” What he meant was, this is only the beginning and each course will build in flavor and excellence. So if I start with “outstanding” that leaves no room for improvement!

The Osteria’s menu varies according to seasonal availability. This means simply that they only use the freshest, high quality local ingredients. From the bread and pastas that are handmade with stone-ground organic wheat, to the perfectly seasoned salads, to the tenderest portions of steak, everything was delicious! After all of this food, how could you possibly put one more morsel into your mouth! Well, you can’t until, you read what is offered on the properly named dessert menu, “Sweet Hell” (taking a little inspiration from the Divine Comedy). It also reads, ‘All Hop Abandon, Ye who enter’. The desserts are named after the seven deadly sins (which after eating a few, my butt agreed that these desserts were definitely deadly!) Personally, I think every dessert menu should have this warning! Obviously, we had to see what all the fuss was about. So, we ordered not one, but two of their famous sugary concoctions! I’m not sure if we were in heaven or hell, but either way it was amazingly sinful

Now of course, during our lunch we had a glass of the famous local Badia a Passignano Riserva Chianti Classico. There is just something so wonderful about sipping a wine that literally came from the earth you are standing on. As we were leaving, we stopped to chat with the local sommelier. Now, I don’t mean some stuffy, guy teaching you to swirl and spit. I mean, real honest to goodness wine expert that not only loves his trade, but has an endless amount of information, history at his disposal inside his head. He told us that the adjacent monastery, that is in the heart of the vineyard, was built and is still occupied by Benedictine monks. He explain to us that the Antinori family who owned this winery, and has been making wine for 26 generations (since 1365) and has vineyards all over the world. Then, he offered to take us into the cellar of that ancient monastery to see where the Antinori family stores and ages their wine. This is not something that is open to the public, so we were quick to take him up on the offer. Once inside this cold, dark, massive cellar, we saw hundreds of oak barrels housing the ‘sleeping wine’. We walked from room to room, learning more and more about the history of the monastery, the monks that live inside and of course of the wine making process.


Once our tour of the wine cellar was complete and our bellies were full, we hopped back in the car with Michael for a nice ride back to the JK Place. Of all the experiences that Rob and I have had around the world, this one is definitely up there among the best. It was truly a once in a lifetime experience!

# # # #

Bravo! offers many types of private, VIP, behind the scenes and exclusive tours and services. Bravo! has the contacts in Italy to arrange unparalleled experiences and services that you will NOT find anywhere else! 

Badia a Passignano’s “La Bottega” and “L’Osteria” are open every day from 10am-11.30pm; La Bottega and the Sala del Torchio are open for tastings on Sundays (10.30am-6.30pm). Tel/Fax: 055-8071278.


  • Reply
    50 Great Places to Visit Before You Die | PrivateJetCharter.net
    July 6, 2010 at 9:02 am

    […] Tuscany: Kim details her recent visit to the Chianti region of Tuscany for readers to enjoy. […]

  • Reply
    Tucson Rental Homes
    January 27, 2011 at 2:20 pm

    Very interesting blog post. Your article is really interesting. I liked this article. This blog post is terrific! I have to say that after continually reading poor as in, same old information, little quality content, etc. article posts on other sites, it’s good to actually read something that has some thought put into it. It’s a pleasure to read quality blog posts, especially after continually seeing rehashed %$!# that writers and bloggers are putting out nowadays. It’s always nice when I come across content that actually has value, I’ve been seeing a ton of subpar writing attempts lately. Anyways, thanks again and I’ll check back frequently to see what else you have to offer. I’ll check back in the future to see what else you have up your sleeve. Keep up the fantastic work! BTW, I like your site design, but your header image was only loading half way for me. P.S. Your header is messed up a bit in IE. The problem could be on my end but I thought you might want to look into that.

Leave a Reply