Travelogue: Tuscany & Umbria, Italy

Travelogue Tuscany

The drive from Rome north to Siena took only a few hours and passed quickly. Once we actually left with the rental car (a process that took far longer than expected), the kids fell promptly asleep in the back seat and Aron and I looked out the window as clumped stone villages perched precariously on hilltops started to rise out of nowhere.

The trick was to navigate up into one!


We arrived in Siena in the early afternoon, hoping to park at one of the lots outside the core of the city and ride the escalator up with our bags. Most hill towns have strict rules about who can drive into the city center and you must be careful to stay out of Limited Traffic Zone (ZTL) areas. Fines are given to drivers who cross the boundaries (Here’s a good run-down on that.)

We had rented an apartment and though we had some general arrival instructions, we spent at least another hour circling until we just stopped at whichever lot we could. I walked into a nearby hotel and asked the front desk to call us a taxi and we caught a ride right to our door.

In retrospect, thank goodness! Every lane is incredibly steep, and if we had had to spend time walking up and down with kids and bags in tow, we would have been seriously hurting! Still, if you’re driving there, be sure to get detailed driving and parking instructions from your hotel. It’s not so simple!

Siena is often referenced in comparison to Florence. It’s the other large Tuscan town—in fact, at one time, it was larger; and whereas Florence is a haven of Renaissance art and architecture, Siena’s aesthetics are Gothic. It is perhaps most famous for its spectacular event, Il Palio, where 10 of Siena’s 17 contrade (districts) compete in a horse race around Il Campo.



We were located just off Il Campo. It was exciting to climb up the hill and descend into the wide-open clamshell-shaped piazza. We decided to choose one of the bars facing the Palazzo Comunale and its soaring Torre del Mangia, and watch Hudson run up and down the the lines along the square. There were just enough cars (locals and taxis are allowed in the center) that you can’t be completely care-free about traffic, but the piazza is pedestrian-only and ideal for kids. Still, Hudson ran up a different line one time and losing sight of him for even a minute makes one’s heart skip a beat.

Our dinner that evening was one of my favorites on our trip: Enoteca I Terzi is a wine bar with fantastic food (it changes every two weeks) and a nice little space to eat outside. It’s just far enough off the beaten track to feel like you’ve discovered a gem. Aron had an incredible squash blossom soufflé that was particularly memorable, but everything was delicious. We would often take bits of our food and put it in this teether for Skyler to try and she was equally delighted.

The next morning, after some coffee, we made sure to get an early start to climb the tower. Only 30 people are allowed to climb to the top at any one time, so we feared a wait. I’m not sure if we were just lucky, but we only waited about five minutes until it was our turn.

It was easy to get Hudson excited about this one: “Hudson do you want to climb that tall tower!?”

Hudson loved climbing all the steps and when we got to the top, we’d gone quite high: “all the way to the clouds,” according to him. It was a clearly a thrill. (Not one for the claustrophobic.)

The views, as expected, were wonderful. When you’re in the city center, the buildings close off much of the light and you’re in a sort of maze. It was like seeing its secrets.


For lunch, we stopped close to someone playing a classical guitar, drawn over by the promise of truffles. Little did we know that we’d find truffles on many menus! (Though can you really have too many?)

After lunch, both kids fell asleep in their strollers and we had the chance to walk all over the city. As soon as you’re off the main roads—Via di Città, Banchi di Sopra, and Banchi di Sotto—it’s very quiet. We saw more signs of the University and its student population and fewer silk Palio flags.

It was a nice break, after which we visited the Duomo—which was magnificent!

The Gothic facade is made up of multicolored marble and painted decorations that look almost like spun candy from afar. I couldn’t remember seeing anything quite like it. 

Inside it was just as stunning: 13th-centurty stained glass, black and white striped tiles, and bright blue arches. We were incredibly lucky to arrive during one of the two months in the year when the floors—scenes of painted marble that took over 200 years to finish—are uncovered. (They’re too fragile to be exposed for longer.)

We decided to go vertical again and climb the church’s unfinished nave. (It was intended to make what would be the largest church in the world, but the city was struck by the bubonic plague in 1348, and the population was decimated.) For this one, we did have to wait. 


The hour of the day made the views even more fantastic this time than the last, and you get to see the duomo and the bell tower. (It’s a little like Top of the Rock vs Empire State Building, right?) But I’m not sure I would recommend this trip with small children unless you feel very confident that they will be good listeners about climbing, etc. The walls are very low and it was slightly windy. We definitely felt a bit on edge while up there.

Dinner that night came from a recommendation I received over Instagram. (So cool when that happens!) Osteria “il grattacielo.”

I love that our restaurant had no menu—just a man attempting to explain that evening’s options to us. One can either walk up to the counter and point to the verdure sott’olio (marinated vegetables) and affettati misti (cured meats), or order off of the small chalkboard menu which essentially indicated that we choose our noodle (Pici, the local pasta, or paparadelle) and then the one of three preparations. 

Around the corner was a Grom gelateria—the perfect finish.


Siena was a wonderful city and was rightly called by one of our guidebooks “the ultimate hill town.” It had all of the earmarks one hopes to experience—the narrow lanes, the steep climbs, the stunning setting, a village-feel—but also some of the benefits of a city, like a vast array of restaurants and sophisticated shops that cater to locals and tourists alike. It draws crowds, but never felt ‘ruined’ as a result.

The following morning, after our coffees and a little shopping time (for me) and running time (for the fellows), we had a quick—delicious—pizza lunch and caught a taxi back down to the parking lot at the base of the city walls.

Terre di Nano, near MONTEPULCIANO

Our next destination was an agriturismo called Terre di Nano, situated in the hills of Montechielo, just outside of Montepulciano. It had come highly recommended by online-friend Vanessa Boz (Boz Around) and Yolanda Edwards (momfilter), and we were very excited about our five nights in and around the hills of Tuscany in the stunning (and UNESCO-site listed) Val d’Orcia.


Even more so, once we actually arrived.

We’d reserved the Terazza apartment, one of the two family suites, situated upstairs above the wine cellar and main office with two bedrooms, a family room—and a large terrace overlooking vineyards and a view to Montepulciano. The other family apartment is called Cassetta and looks toward Pienza. Cassetta has the more classically glowing sunset view, but we found we appreciated that our apartment was slightly further from the main house, with a closed-in terrace, to ease our minds about whether our kids would bother anyone.

Immediately upon arrival, Aron ordered some wine (they make their own there) and we opened up the cheeses we had purchased at Il Campo de’Fiori before we left Rome.

Later, we realized, we should have made shopping (and stocking the kitchen), even more of a priority so that we would be likely to fully take advantage of the low-key setting. It was our intention, many times, to do so…but often we would get distracted.

You can have dinner at Terre di Nano’s restaurant (and perhaps ask for it at your apartment?) most nights of the week, but you have to reserve ahead. Before our trip, we had asked to have dinner there on our first evening.


While we were waiting, we walked around the grounds some more—Hudson fell in love with the three beautiful Bracco Italiano dogs, and found lizards and grasshoppers among the plants (I think he loved that additional freedom of not being in the city), and Aron and I looked out at those totally unreal, jaw-dropping views with a sort of ‘forehead-smack’ realization: “Oh! this is why everyone loves Tuscany.” It was prettier than I’d even expected and we couldn’t stop snapping photos.

We had asked our host, Giorgio, to make us dinner there that night—and I wish we’d done that at least once more. We had a great multi-course meal and Hudson could still get down and explore the patio a little bit in between. Nearly everything came from their garden or farm, including the wine! All the food was delicious. 

I especially loved dessert, which was so simple! A glass of Vin Santo with a plate of biscuits. We took home a small bottle and plan on recreating that meal’s end sometime when we are missing Italy.

Our intention was to really slow way down that week: you know, breakfasts on our terrace, a card game while the kids napped… no real plans.

But we’re impossibly restless, I’m afraid, and we couldn’t bare not to see more of the surrounding towns and those iconic views. So we ate breakfast back on the restaurant patio and got back in the car right afterward on the following morning.


We drove all the way out into the Crete Senese (Sienese Clay Hills), to the village of Asciano—where we’d heard there would be a morning market. It was quite small, and the town had virtually shut down for siesta by the time we arrived, but we got there just in time to pick up some burrata, bread, and a slice of porchetta (stuffed, boneless pork that Aron had come to love in New York—but which is native to Italy).

On our last trip, we made the mistake of thinking pesto would be available in all of Italy. Aron didn’t want to make that same mistake and assume he’d have more chances for Porchetta. 

We set up a small picnic on a bench beside a playground. Finding a place where our children could play while we enjoyed the food we’d gathered at the market was a win-win. Although in retrospect I might recommend a different park—the one we came across later in San Giovanni d’Asso.

We drove along the road to the Abbey of Monte Oliveto Maggiore, which would be lovely around sunset—especially if you could time the drive to get you to the Abbey for the Gregorian chants. But by the time we arrived, both of our children were asleep in the car. We were very reticent to wake them and decided to send Aron as a scout to see if this was worth doing. As it turns out, the church was closed. Another reason to return I guess.

But only a little further down the road, we came to the town of San Giovanni d’Asso, which sits in the heart of the truffle region. Signs started to appear along the road indicating as much and then we saw a marker for a truffle museum. We had to go—especially with my dreams of being a truffle grower!

It was an earnest attempt at showcasing the truffle—with exhibits on detection and smell—but I wished they’d had more colorful history. There have to be some tremendous stories about theft and rivalry, about wealth and about the poor person who ate something he dug up that was not a truffle…


There was a small park across from the museum with a very nice playground and swing set, and a big grassy lawn with a few picnic benches overlooking a view of the hills. This would be the place I’d suggest a family with small children stop for a picnic.

We ended up in Montalcino, a truly magnificent place to drive up to that’s known best for its Brunello wines. We lucked out, and the city was celebrating with an event called Notte Bianca, and had very affordable tastings set up at stands around the village. Later that night there was to be a dance party, but it would start way after bedtime.
Instead, we climbed up the fortezza for views of the valleys and into the city. The fort is mostly empty, save for a wine bar where we sat for a plate of misti and a couple glasses of wine. Hudson was being particularly…um… spirited, so we didn’t linger, but as usual Skyler got lots of special attention from passers-by. 
We opted to cancel our dinner reservations (that we’d made close to our home base) and stay in Motalcino for some pizza-to-go.
It was a good decision: Hudson ran off some steam with a balloon sword and a group of kids in the piazza, we got our chance to taste some legendary red wine and do some window-shopping (so many beautiful leather bags!), and there was a shop selling Nutella gelato—pure nutella that had been frozen. So good!

The following morning, after breakfast from the restaurant (we really kept meaning to stock that kitchen!), we sought out the thermal baths at Bagno Vignoni.

It turns out, there are hot springs are all over Tuscany! The thermal waters there have been in use since the Etruscans. 


One comes into town and first passes by the “Square of sources,” which contains the original source of water. If you walk through town, you’ll find the modern pools at Hotel Posta Marucci. 

There were two pools, each a different temperature (so you should choose the one that you felt comfortable in). There’s a small fee, and you’ll need to shower and use a bathing cap before entering (which is really pretty nice). Around one o’clock, the pool empties for a cleaning closure, so we took that as our cue to go get some lunch at a spot we had stopped to reserve at on our way through town earlier—Osteria del Leone.


It was fun ordering Hudson appetizers as his meal… things that I really wanted to try (but thought he’d enjoy, too)—as was the case with those ham-wrapped, cheese-stuffed zucchini blossoms. Delicious!

I was very interested to find that almost every panzanella salad we had while in Tuscany was made with such finely crumbled bread (and served very cold). Here, one almost always sees crouton-sized pieces of bread tossed with tomatoes, whereas this was almost the texture of cous-cous. It was one of Skyler’s favorite dishes—perhaps second only to pizza crusts.

Also pictured here was my favorite truffle dish on the trip.


That evening was the Bravio delle Botti in Montepulciano. A challenge between the eight Contrade wherein two athletes, called Spingitori, roll 175-pound barrels uphill in a race along the main street that runs through the historical center of town to the Duomo in Piazza Grande. There’s a procession starting at 3pm, so we were concerned when we arrived around 4 or 5 that we wouldn’t find a spot. Fortunately there seemed to be some leniency that night about what constituted a valid spot. Let’s just say we were glad it didn’t rain or we’d been fearing our car would have slid down the hill.

Waiting for the race to begin, there was so much excitement and anticipation palpable among the crowd. We found a spot by some older citizens who were such fans of the kids that even once both Hudson and Skyler were back with Aron, they all pushed me in front of them for an unobstructed view. The racers passed in a flash!

Walking around after the race, Hudson was inspired to run up the hills himself. But then he started to cry when he realized he didn’t have a barrel to push. “Where my barrel go?,” he asked through tears.





Whereas some towns are known for wine or hot springs, Pienza is known for cheese—specifically Pecorino cheese.

The weather had turned for a cold snap, so we were struggling with how to still enjoy what we had envisioned as a warm-weather outing. But we passed the time just fine going in and out of cheese shop after cheese shop, admiring the selection.

Hudson even got in the spirit: When I asked Aron to pick up some cheesy breadsticks for Hudson’s snack, he interpreted that to mean a small log of cheese that was next to the check-out counter. Fortunately, Hudson loved it and knawed on it for the next 20 minutes!

Finding a dinner spot to please everyone can be challenging. Something easy? or something good? Can it be both? And how do we find it in time when everyone is hungry?

Almost all of our books recommended a restaurant called Ristorante La Grotta, just outside of Montepulciano by the San Biagio church. We drove out and I had Aron run in to see if it would really be okay with kids: it looked intimidatingly fancy and was prefaced by the word “Ristorante,” which I had avoided as a rule in favor of more casual “trattoria” or “enoteca.” He said they’d been very warm and encouraged the kids, so after taking in the amazing sunset, we geared ourselves and our son up for some good restaurant behavior. It was quiet… with white tablecloths, but everyone was so welcoming—even bringing pillows over to raise the kids up. With a few books and a little rule-bending—like some iPhone use at the appropriate moment—Hudson was perfect, and it was a wonderful meal.


On our previous day’s journey, based on the recommendation of our host, we had stopped off at Cugusi cheese farm and vowed to return for breakfast the following morning. It turned out to be one of our favorites—and a highlight of the trip: we had yogurt and honey and crackers and ricotta so fresh it was still warm.

Did I mention that we think a great vacation for Hudson would have just been playing with these dogs all day long? He loved running after them and petting them and was always watching to see what they were doing.

Inspired for a little variety, we decided to walk to Monticchiello from Terre di Nano. It was great on the way down. The way up was another story: Hudson wanted to be carried most of the way. (Aron of course came through there. And then he came through again when he ran back to our place solo after lunch and picked us up in the car. But I promise it wasn’t that far if you were going to do it yourself… just a bit steep.)

While we were there, we confirmed our dinner reservations for that night at La Porta—one of the other restaurants that came most highly recommended. We asked to sit outside; the host said he would reserve an outside table but made it very clear that we could not come back inside. No changing. Pressure! I had not properly prepared for the weather and quickly dashed back to Montepulciano to get Hudson and I jackets. I told Hudson his was an Italian racing jacket—and then it was difficult to ever get it off him! 

The views at sunset from Montichiello were incredible! It would be worth a stop for that alone. But I think the cold evening (though we really were fine, as we were protected from the breeze and the restaurant even gives everyone blankets) along with the dark, and the somewhat uncharacteristically stuffy attitude of the waitstaff made this restaurant meal feel like the most challenging of all. And if I would to do it again I would probably have lunch here instead of dinner (or at least sit inside where it’s louder). The funny thing is, I got the impression that our kids weren’t really welcome (even though they were very well behaved), but then I noticed a box of toys sitting beside the restroom, on hand for guests. So who knows?

Hudson did have his favorite ravioli here. We ordered him a truffle ravioli dish (those items with truffles usually only cost one or two euro more) with the intention of sharing. In the end, we got very limited bites.

We bid farewell to Tuscany, but not before making one detour to a winery. Icario’s setting was a bit sterile, but we chose to take home a bottle to open in the distant future.




Many people choose to start their journey from Rome to Tuscany & Umbria in Orvieto, as it’s conveniently on the train line. But we ended ours there.
We had a small apartment (or family suite) in B&B La Magnolia—which I’ll now fondly recall as the place Skyler began crawling. Our host, Serena, was so kind and easy to communicate with in advance of the trip. She gave wonderfully detailed instructions for arriving and parking—but somehow we still messed up and ended up doing about an extra hour of circling. At one point, a nice motorcyclist asked us where we were trying to go and went out of his way to let us follow him.
I can imagine, that if one is planning on doing a lot of daytripping to larger cities (like Orvieto or Assisi), these kinds of confusions could really eat into your day. I was glad we would be staying put for a bit.


Our host recommended lunch at Caffé Montanucci—and we ended up eating there one or two times more!—it was such a great option for us, with the kids: you select items from cold and hot-food cases and they’re prepared as necessary and brought over. They’re also open from 7am to midnight! Their dinner menu, however, is more traditionally served. But at this point, we were ready for some more low-key meals and were happy to find such a great option that also happened to have great ambience.

There was a news cafe/bar where people would gather and stand; the bottom floor (where the host was apt to recommend families sit) was lined with magazines; a sun-filled atrium could be accessed from behind an island of books; and there were wood carvings by Bottega Michelangeli throughout.

Those wood carvings, which could be found throughout the city (even in our apartment!), were one of my favorite things about Orvieto. They were modern and scultptural but also part of a five-generation family tradition … What a treasure!


While in Orvieto, we took a ride up and back in the funicular to the base of the hill (where the train station is), strolled with gelato in hand, visited the farmer’s market, climbed up the tower (Torre del Moro) to hear the bell ring, and walked up and down Corso Cavour many times over.




I didn’t take any photos in the evenings over dinner, but the evenings were relatively quiet in Orvieto—after the daytrippers had departed—and I quite enjoyed that! Our first night, we stopped at Trattoria del Moro Aronne just before they opened, and it was a good thing: within the first half-hour of our sitting down, they were turning everyone else away for the night. We made sure to try their famed nidi (pasta with pecorino and honey) as well as some wild boar.

Hudson had one of his most memorable meltdowns here. It pretty much the essence of a “toddler moment” like the ones I mentioned. This makes me laugh now, but you know how it goes… it didn’t really then.

We were in the bathroom together and it was my turn to go. By this point, he’s gone and I’ve done a little dance around him in a crowded, poorly ventilated stall to get his pants down and up and the whole drill and I’m telling him not to open the door. Then, he asks if he can wipe. (For me, that is.) And of course I say no. Cue tears—big, head tossed back sobs. He asks if he can throw the paper away for me. Again, “No, Hudson. We throw our own paper away.” (Which, truth be told, he doesn’t get to do yet since I do the wiping for him, so… there’s that.) As soon as the paper goes into the bowl, he is crying (almost screaming) and throwing himself onto the floor. (The bathroom floor! Ew!) “Get up! Now!” I say in a tone that I’m not totally proud of. “Hudson! You’re being RIDICULOUS!”

He snaps out of it. “Roodiculous? Like ‘ROO-diculous!’ Like in Roo in my Winnie the Pooh book!”

He wipes his eyes and opens the door. And it’s over. Just like that.



In the afternoon, we drove to Civita di Bagnoregio—a traffic-free village with only a handful of residents, connected to the modern city of Bagnoregio by a pedestrian bridge. It’s a favorite of Rick Steve’s, but otherwise there’s not much about it in a lot of guidebooks (as far as I can tell). I’d suggest using his directions for visiting, if you are in the area.

We only stayed within the town briefly—there are a few open cafes but the town is more like a ghost-town than a living village. What’s really magnificent is the view.


If you’re nearby, it felt like one of those sights that you can’t not visit, even if you know what it is going to look like. The approach to it is truly stunning, and the city looks amazing from every angle. Also, the drive through the backroads around Umbrian Orvieto was lovely and afforded us a terrific look back at our home base. 


And with that, it had come time to go to the beach!

Coming up next: Positano & the Amalfi Coast

P.S. Our travelogue from Rome, the first leg of our trip.

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