The Boot Camp Part 5: Tuscany 1




There’s a reason Tuscany is one of the most talked about destinations in Italy. Tuscany is a unicorn; a mythological creature that doesn’t exist except in fairy tales, but part of us still holds out the hope of finding one some day anyway. Tuscany is like a hot guy who’s also smart and good in bed and likes to cook. Tuscany is sort of perfection.


In a country of world class wine, the wines of Tuscany are my favorite. In a country known for amazing food, the dishes of Tuscany are among the best of any trip I’ve taken. In a country known for it’s stunning beaches on the coast and its picturesque undulating hills of vines inland, Tuscany has both. It is literally all that and the David.


I’ve never had a bad meal in Tuscany. And some of the best wine in the world is local and very affordable. You go here to eat and drink and life is good. Tuscany is a fairy tale, right down to the castles that crown the top of each hill town.


Gnocchi in Poppi saved the day!

Gnocchi in Poppi saved the day!

Speaking of hill towns, Tuscany is lousy with them. And I strongly encourage you to get in your car and drive around to the smaller ones for a meal and some tourist-free walking around. Be open. One rainy Sunday in May we arrived in the town of Poppi which we knew zero about. It was lunch time, and I was worried we were going to miss the lunch hour if we didn’t find someplace to eat. Italy has very specific hours for lunch and after that restaurants won’t open again until dinner. My fear was compounded by the fact that at the moment, Poppi was a ghost town. There was no one walking around in it at all. Perplexed, we walked up street after street looking for a place to eat. Finally, we heard the sound of silverware on plates. It was faint but we followed that sound until we found a small restaurant where 6 Euros bought you a plate of homemade gnocchi in the sauce of your choice. It was the perfect rainy day meal and for $28 we each got a pasta and a 1/2 litre of wine, as well as the pleasure of watching the owner yell at her son and daughter after explaining to me in Italian that she was trying to teach them the family business and they didn’t care. Authentic and delicious!





Montalcino was my first ever destination and as such, still one of the closest places to my heart. With the major part of the town more or less two streets, it may be too small and sleepy for you, but to be fair I was there in March so in high season when the major destinations are overrun with tourists, it may be just right.


Villa outside of Montalcino. Possibly Caparzo, but I don't remember because wine.

Villa outside of Montalcino. Possibly Caparzo, but I don’t remember because wine.



We stayed at Il Giglio,  a nice little hotel in the middle of the walled city, where they will give you a parking space and even park your car for you, which is helpful because the streets are very narrow and you will scrape your car on more than one wall. (I recommend getting car insurance with a  zero deductible.) And speaking of cars, I always use AutoEurope when I travel. You may be able to get a cheaper rate, but I like that Auto Europe is an American company and therefore the prices quoted are in dollars which is handy and every customer service issue I have can be dealt with someone in English. This is a huge help as plans change and get thwarted. Most Auto Europe cars are rented through Europcar locations, so once you get over there, you won’t have the luxury of dealing with some kid in Maine. Still, I’ve never had a problem. Also, you can get the no deductible plan for insurance. Take note, last I checked all those fancy features on your AMEX like automatic rental car insurance DO NOT apply in Ireland and Italy. Last I checked. So make sure you have that covered before you go. And FYI, you do not need an International Driver’s License to rent the car, but if you get pulled over by the Polizia they will want to see it. So it may be prudent to get one before you go. AAA can help you there.



Montalcino was the beginning of our travel philosophy, “Follow the wine.” We figured when in doubt, go to a place known for their wine and we couldn’t go wrong.

The view from & at Caparzo at 10 am.

The view from & at Caparzo at 10 am.

The home of Brunello, there are many wineries in the area where you can either set up your own tastings, or to make things easier, arrange a guide to do it for you. I’ve used Very Tuscany Tours  a couple of times and recommended several friends to them too, who’ve always been happy with the results. Andreas will pick up, drop you off, and help put together exactly the experience you’re looking for in between.


If you decide to strike out on your own, I recommend Caparzo which is on the larger side that your probably used to in the states and for smaller, family run places there’s Sesta di Sopra and Stella di Campalto.

Me & Stella.

Me & Stella.


The day we went Stella herself took us around and we got to barrel taste wines from the various fields and it was amazing how the same grape (Sangiovese) was transformed by the minerals or the clay or how much sun and wind it got.


You can also taste plenty of wines without getting in a car. There are many smaller tasting rooms around the town and a the Enoteca la Fortezza  you can both taste wine and get your culture on. And old fortress, you can tour it to see some amazing 360 degree views of Montalcino and the Val d’Orcia below and the once inside you can taste as many as 10 Brunellos at a time as well as local cheeses, olive oils, meats and honeys. We went there three times in the two days we stayed in the town, often forgoing lunch for a plate of pecorino cheese and wild boar salami. Then a few days later on our way to Pienza we stopped by with friends who had just gotten to the area. We ordered so much food and wine they had to put some of it on a separate table, especially after we ordered two 10 Brunello tastings and rather than bring us the same 10, they offered to bring us 20 different wines to try. It was magnificent.


If you don’t forgo lunch, I recommend Il Grappolo Blu. I’ve eaten there twice, both for lunch and dinner, and still think about their wild boar and polenta and tagliatelle with truffles to this day. Speaking of, get ready to get your truffle on. That’s going to be a theme throughout Tuscany.


Just outside the town is the Abbey of Sant’Antimo, a former Benedictine monastery dating back to the time of Charlemagne, where you could still hear the monks holding mass in Gregorian chant which will send shivers of peace up your spine no matter what your faith. Unfortunately, when researching this I just learned that the monks were departing to go back to France and there was no word on whether or not they would be replaced with a new order, let alone one that chants.


Sunset viewing in Pienza

Sunset viewing in Pienza

Close to Montalcino are the towns of Pienza and San Quirico. An entire side of Pienza overlooks the Val d’Orcia and everyone in town gathered there at the end of the day to grab an appertif from a local café and watch the sunset. San Quirico had a charming and authentic main square where we enjoyed glass of wine along with the locals who were sipping Campari before eating dinner at Trattoria al Vecchio Forno.


Also not too far away is Montepulciano, a larger town that is a little more touristy, but also may be a preferable base for you as it just has more to offer in the way of places to stay and eat. It’s also closer to A1 and from there you can day trip to Cortona, Florence and even Orvieto in Umbria. The town itself is lousy with tasting rooms where you can taste cheese in addition to the wine and also wander the tunnels and caves underneath the town where much of the wine is stored.


For food I recommend, Godimento DiVino, where I had some excellent gnocchetti with pecorino and truffles. (This is also pecorino aka sheep country.)




And if you’re feeling adventurous, about 10 km outside of Montepulciano, is a little town called, Montefollonico, where we ate at a restaurant called Ristorante 13 Gobbi. We had been sent there by someone at a tasting room in Montepulciano and we didn’t exactly have what you would call directions. Plus, even though there were only 5 of us, we had 2 cars. We followed the first car for awhile before we pulled over because they were lost. Then our car took the lead, but for awhile we weren’t sure we were headed in the right direction either. We had no cell signals, therefore no GPS, and when we finally got more than 1 bar again everyone jumped on Facebook to upload the pictures from the day which made our driver (my husband) rather annoyed. Eventually, we found the town, parked and hurried to the restaurant only to be told they were completely booked up for that night. Disheartened we walked away completely at a loss for what to do. That’s when I saw the window of 13 Gobbi and said, “I’m eating here.” The Husband, never one to make a quick decision, prevaricated with a lot of talk about reading the menu and looking for someplace else and I said, “You do what you want. I’m eating here.” In the window, I could see the owner tossing plates of hot pici pasta inside a gigantic pecorino cheese wheel. That was all I needed to see.


Likewise, there’s also a small town near the Umbrian border called San Casciano di Bagni where there’s a tiny restaurant called Ristorante Daniela that had amazing pigeon ravioli. I know. Just go with it. It has a rich flavor like a buttery turkey that was on my lips for days. There’s also supposedly a hotel with a great spa in the same town.




Cortona is famous for being the setting of Under the Tuscan Sun, but don’t hold that against it. It makes a great base of operations from which you can go to Montepulciano, Orvieto and the Province of Umbria and even Florence. Plus there are a couple of days worth of things to do there, with a Fortress being all the way at the top and some Etruscan ruins being at the bottom. Also, I got a great pair of shoes there.


The town is also full of tasting rooms. Unlike the rest of Tuscany which only has eyes for Sangiovese, Cortona is trying to push Syrah. We stopped at the tasting room for Romeo, a winery that is actually based out of Montepulciano, and had such a fun time with the other tourists who were sheltering from the rain and the outgoing woman who ran it. And from the reviews when you google “Romeo Wines Cortona” other patrons seemed to agree.


Speaking of Under the Tuscan Sun: one year we did the thirtysomething right of

The backyard of our Villa in Subbiano.

The backyard of our Villa in Subbiano.

passage and rented a Tuscan villa with friends. We used Rentvillas. While looking we also had an excellent experience with Emma Villas. Ultimately Rentvillas had the property that most suited our needs for that trip, but Emma had both excellent customer service and properties.




Siena is a popular tourist destination, almost too popular. Don’t get me wrong: it’s still Tuscany. The food is excellent, the Duomo stunning in scope and it’s in the chianti region if you want to do wine tasting. But I found it lacked a personality and charm that I find in other Tuscan towns. In addition to the food and monuments, I’m looking for something authentic, a place or experience. It seems everywhere else I’ve been I’ve wandered into someplace unique: an artist’s studio, a gallery, a local made jewelry store. Sometimes it’s an enoteca with a chatty hostess or a boutique with something special and a friendly owner. I’m looking for something that I can’t get in America or in every other city in Italy. We wandered all over Siena for two days and I never really found it. The stores were hopelessly generic: the exact same stores you find everywhere in Italy. There were no hidden gems and as such it lacked a personality to me.


Some will argue that Palio, the twice-yearly horse race held in the center of town where representatives from 10 of the 17 neighborhoods compete, is plenty of personality. It just doesn’t quite resonate with me. I feel badly for the horses.


View from our room at the Ravizza.

View from our room at the Ravizza.

However, we did stay in a fantastic hotel, Palazzo Ravizza, where I would go back to in a heartbeat.  There was a gorgeous garden overlooking the countryside where you could have breakfast or just a glass of wine. Speaking of wine: they had the most amazing wine dispenser in the lobby where you could purchase fantastic glasses of wine for a couple of Euros.

We ate dinner one night at La Taverna Giuseppe, which was big and crowded and felt a little like a factory, and the waiter tried to talk me out of ordering the Canonau I wanted in favor of an overpriced local wine, but that didn’t stop me from enjoying the shit out of some cocoa pasta in a wild boar ragu, the chicken liver fegatini, or a quail egg and sausage on polenta.


If you’re looking for a smaller and more intimate place, we had a delightful lunch at Antica Osteria Stelloreggi the type of place that has a handwritten meny and a friendly waitress who is happy to point out what is actually better than what you want to order. She wasn’t wrong: my homemade tagliolini with truffles was delicious.


Osteria Da Divo was on the fancy side and claimed to be Tuscan “with a twist” but still was very solid meal of porcini stuffed rabbit, stuffed pork and more gnochetti and truffles. We ate downstairs in what appeared to be a “cave” – whether it was real or fake was unclear. I remember the wine being good, but overpriced compared to the rest of Tuscany, a common thing in Siena, I found.


There’s also a lot of tall stuff to climb in Siena. There’s the Porta del Cielo at the Duomo, the Panoramic View next door and the Torre del Mangia.


The Duomo itself can be overwhelming: there’s more overdone things to look at than a Kardashian Christmas card. Pace yourself. You don’t have to see everything. In fact, I think it’s better if you don’t. I much prefer to enjoy one or two paintings or chapels fully, then to try to squeeze it all in and in the end not know what I looked at. There is a beautiful library there filled with hand painted pages of old books. And crowded into this library were people with their iPads out, mindlessly recording everything in one big sweep. I wonder if they took any of it in, and I doubt they ever looked at those videos again. But I remember the one illustration that particularly captivated me. And you can always spend 1E on the postcard if you want to take that memory home.




Capalbio is a charming hill town in the Maremma, the wine region known for Morellino di Scansano wine and its proximity to the Tyrrhenian Sea.  We ate at Il Tullio our first night and I was so blown away by smoked chianina carpaccio, baked pecorino with truffles, and rabbit braised in red wine, that we went back 2 nights later.


Capalbio is home to French sculptor Nikki di Saint Phalle’s Tarot Garden, as well as some of the warmest beaches I’ve ever experienced. While I’ve become a fan over the years of the “refreshing” waters in Italy, the warm sea near Capalbio was pleasant and may be more to your liking. There’s also actually sand there, unlike many of the Italian beaches which are rocky.


About 30 minutes from Capalbio is the Argentario, an island-like promontory connected by a roadway to the mainland. The Hamptons of Italy, it is perhaps most

View from the room at Cala Piccola

View from the room at Cala Piccola

famous as the place off of which the Costa Concordia went down. We stayed at a hotel right on a cliff called Torre di Cala Piccola. Everything you read about the hotel is true. The wifi is spotty. The rooms are OK. The service is “eh” especially at the overpriced restaurant which you will have to eat at if you don’t want to brave some really treacherous, unlit driving at night after a few glasses of wine and don’t want to spend money on a taxi. But the view is spectacular. There’s a wonderful bar area where the food is actually pretty good, although unfortunately not open at night, and it’s on the edge of the cliff, looking out over the water and magical at sunset. And the beach, while a walk from the hotel and nothing too fancy, is pretty great, too.


Lunch at I Due Pinni

Lunch at I Due Pinni

If you do go to the Argentario, I recommend I Due Pini  for lunch. Right on the beach it has really fresh seafood and is a great place to have linguini with more of the delicious bottarga that is available all over the seaside and a Maitre’d who wore an apron, but no shirt or shoes. Come on! How great is that?




The beach near Cala Piccola

The beach near Cala Piccola





This is one of those more touristy towns, but the year I stayed there it felt like all of the tourists cleared out by evening and the streets were quieter when you walked to dinner. There are two gigantic towers to climb if you’re one of those people, and I was even able to have a few more authentic experiences, talking to a man in a jewelry store and going into a gallery of local artists. We stayed at Hotel Leon Bianco which was right off the main piazza and had a charming view of the cisterna and ate dinner that night at La Mangiatoia, which came recommended by two locals and lived up to the expectation. In my notes, I wrote that it was the best meal of my trip. We enjoyed a crepe with pecorino and truffles, pasta with wild boar ragu, artichokes which were in season, white beans, a venison cooked with porcini and Vin Santo, and cheese with truffle honey for dessert. And of course, Brunello.


Drinks with a view.

Drinks with a view.

Also, at one point The Husband and I stopped for a glass of wine at a café in the main piazza. We walked in, the down some stairs, then across the bar and then down some more, until we came out onto the edge of town. Despite the fact that it had looked dark and small when we entered, when we eventually sat down, we were sitting on a sunny terrace overlooking all of the Tuscan countryside. That’s the wonderful thing about travel: sometimes you just don’t know until you walk in.


Boot Camp Part 6: Cinque Terre




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One thought on “The Boot Camp Part 5: Tuscany

  • Patricia Genser

    Tess, your insight and suggestions are remarkable and so welcome. I am Andrew’s mom and greatly appreciate the specifics. Thanks so much.