An aproned waiter stands over your shoulder, impatience tightening his smile. You are sitting with your friend Kara on the terrace of the Osteria del Teatro, in Cortona, Tuscany, a yellow stucco house on a curved cobblestoned street. Now and then, map-toting tourists emerge in pairs or small groups, sometimes arguing over their location.
The waiter explains that cipolla dorata al cartoccio is an onion cooked at a low temperature in a “cartouche”. You look at Kara, who shrugs and nods.
You also order zucchini flowers stuffed with ricotta and the duck with fennel tagliolini, though not the full Italian coursing. You need to get to the next town by mid-afternoon.
In planning your six-day journey from Tuscany to Piedmont, you knew there’d be echoes of that well-worn genre, the buddy road trip. The fact that you’d be stopping in vineyards along the way brought expected jokes from friends about reprising Sideways, though your route owes more to The Trip to Italy.
On top of which, you’re sitting in the exact medieval hill town that Frances Mayes put on the map with Under the Tuscan Sun (and where the Diane Lane movie was filmed), ushering in herds of middle-aged women seeking romantically crumbling villas and self-fulfillment.
Now that you’re here, you feel a bit embarrassed that your crash course on the Italian countryside relies on so many cultural clichés and beaten paths. You’re a travel editor; any pretense of discovery has vanished with the crowd of sweat-suited Americans entering the church you were going to visit after lunch.
How on earth will you blink away so many familiar images to see this place with fresh eyes? Italy, you acknowledge, can sometimes feel like a chord of music you hear resolving four beats before it actually does.
And yet you wrestle with the voice of the novelty-chasing snob for only so long before the honeyed, terra-cotta glow of the buildings in the piazza stirs an urge to sit and watch the early September sunlight melt down their facades.
The sound of church bells and the clatter of feet on cobblestones, even the foreign purr of a diesel engine, calm your synapses.
At the table, your dish arrives, a large onion encased in cellophane cinched with a red string. A waitress, not the man who took your order but a woman who meets your surprised look with a laugh, unties it and folds back the plastic so the sweet juices can run out, then nods at you as you peel back the skin with a knife and slice the tender layers. Right, you think. The journey is the point.
Kara is your friend from a previous publishing job—you were “work wives’’—and now that you’re at different companies on opposite coasts, you miss the easy camaraderie.
She is also, flat out, one of the most capable people you know, time and again taking charge when projects threatened to go off the rails. In that peculiar dynamic of the office, you each revealed intimate details of your lives without ever once setting foot in the other’s home.
Aside from the fact that Kara knows a lot about wine (she once dated an importer), you had a feeling she’d make an ideal travel companion, which bore out on the very first day, after you took the wheel of the tiny black Lancia rental and nearly fried the gears shifting up the Tuscan switch- backs, prompting Kara to gently (but firmly) relieve you of driving duty.
“This thing corners like it’s on rails!” she shouted, banking around another turn.
You’ve hit enough of these Tuscan hill towns in two days that you find yourself making snap judgments about their appeal.
Montalcino feels museum like, with polished storefronts hawking Brunellos and neat rows of pecorino, whereas Pienza has an ineffable charm—maybe it’s the shop selling modern versions of the linen tablecloths you see everywhere, or the two young Italian mothers sipping wine over a long lunch while dandling their toddlers on their knees.
Similarly, the sheer number of churches in these towns is overwhelming, and you wander in and out of them—some decked out with Renaissance oil paintings and stained glass, others containing little more than humble wood ceilings and a cross—in a Goldilocks search for the just-right vibe. The things that grab you also surprise you.
After visiting the Basilica of Santa Margherita in Cortona, in which the body of the 13th- century saint is laid out on a red satin pillow, you walk downhill past the tiny 15th-century church of San Niccolo, behind a grassy courtyard. Intending to skip it, you are practically pulled inside by a brown mutt that runs over to greet you.
Inside view of Basilica of Santa Margherita – Cortona
The room is a dusky blue box with a squat side door bored through with wormholes and sized for a child. On the cloth-covered altar sit two cloudy crystal holy water pitchers hand-painted in gold trim, beside which lies a crumpled linen napkin, looking as if it had been dropped by a priest called away in a hurry. You find you can’t take your eyes off it.
You are staying down the hill at the Villa Loggio, a peach-hued estate where statues of classically draped women bake in the sun and a gleaming oval pool overlooks a valley of vineyards.
It is run by Sara Ensing and Fidelis Suttmann, young German siblings living the Tuscany Plan B fantasy— or, rather, expanding on the fantasy of Sara’s ex-husband, with whom she originally acquired the property and vineyards.
Sara, a tall blond whose heels and dress convey a resolute professionalism in spite of her rustic surroundings, runs the inn with the help of her housekeeper, who now works in the kitchen turning out hearty regional home cooking.
You sit outside for a dinner of figs, pecorino, and prosciutto, with a glass of their fruity viognier blend, then pasta with wild boar sauce and bistecca from the region’s white Chianina cows, washed down with a meaty syrah.
The siblings talk about winemaking. It’s been a hot and dry summer; now it’s harvest time, and three of their workers have quit. “Wine is all about expectation,” Sara says, and while you know she’s referring to how its quality is judged, the larger implication hangs in the air.
To find the legendary Super Tuscans, those Bordeaux-like blends that put the region on the global wine map in the 1980s, you have to drive west to coastal Tuscany, or Maremma.
Though you have traveled only an hour from Montalcino, it feels like you have entered another country as the landscape changes from dusty red hills to lush fields with bursts of palmettos.
You stop for a swim and a grilled seafood lunch at Punta Ala, a beach resort town empty but for a few Italian families with little kids; summer’s end is evident in the dozens of empty chaises lined up like soldiers at attention.
You reluctantly press on another hour to the Bolgheri region, home to the great wine houses of Sassicaia and Ornellaia. The day’s driving is starting to wear on you, so you stop again for a coffee, in the hill town of Castagneto Carducci.
Road to Castagneto Carducci
In its small piazza, which you approach via ascending circles like an Escher drawing, the town seems to be holding its breath. Out of sight, a car door slams; an orange cat slinks behind a pot of geraniums. You are grateful for these moments of vivid singularity.
Next to the small cafe, a window display with a half-stitched men’s suit catches your eye. You enter and a stocky man at a sewing machine offers greetings in a cluttered room lined with vintage cabinetry, bolts of fabric, and yellowed tailoring patterns.
He introduces himself as Florin Cristea and explains that the shop opened in 1911. A Romanian immigrant, he trained in Florence and worked for the original owner’s nephew, who left him the business.
Cristea proudly shows off a dark-green moleskin hunting jacket he’d sewn, with a pouch on the back to carry a rabbit or pheasant “But don’t use anymore for this, it’s just for fashion now,” he says.
A student comes to help him, he says, but there’s a law that requires paying apprentices. “In Italy it’s so difficult,” he says, shaking his head. “These kinds of traditions are dying out because they don’t give them the right medicine to keep it. Which is freedom.”
Down the hill at Ornellaia, you find that tradition is thriving. Founded in 1981, the 100-odd hectares are owned by a noble Florentine family, the Frescobaldis, who’ve been making wine since the 14 th century.
The rules to attain a Bolgheri DOC label are strict, as the grapes must be mainly a mix of cabernet sauvignon, cabernet franc, or merlot, with no more than 30 percent coming from other native vines.
Every year, Ornellaia’s winemakers play with the formula to arrive at their new vintage, which they release after three years. All of this is relayed with polished authority during a tour of the property’s glass-walled production center and then in a villa-style tasting room by Irene, a young guide in black pencil pants and blouse.
You taste three 2014 vintages, from an entry-level wine to a reserve, the three of you swirling and sniffing and sipping and warming your throats with the full-bodied flavor of sun-ripened fruit.
You are sated and sleepy, and now face a 20-minute drive to the B&B. You pull over in the next town to rub your temples, cursing the distances that seemed so close on the map.
After three days in the Lancia—which Kara dubs “the Nugget”—you have found your rhythm and your roles: driver and navigator; shouter atreckless speeders and placatory. Also, your back and legs ache, like you’ve been on bed rest.
As Kara negotiates the terrifyingly twisty roads of the Ligurian coast, you both consider the unlikelihood of your friendship: You are married with three kids, Kara is single. Given the tribal cliquishness of demographics, some friendships don’t deepen.
Yet workplaces can be equalizers, stripping the usual signifiers from our identities; a road trip—which requires a division of labor, organization, and patience- turns out to be oddly similar.
For days, you were outrunning the shadow of cinematic cliché on your adventure; in Portofino, you pretty much surrender, as you step into a Rock Hudson/Gina Lollobrigida fantasia.
Pink and yellow villas surrounded by bushy palms dot the steep hillside and overlook a small harbor filled with luxury boutiques and superyachts.
The Belmond Hotel Splendido, the clifftop former monastery where you’re staying, feeds the effect with its old-world reception area and a white-haired bartender of 47 years named Antonio, who mixes bellinis for men in gold-buttoned jackets and sockless loafers, with women in bandage dresses carrying glossy shopping bags.
At the base of the ascent to the Splendido, a tiny, comma-shaped man with corn-silk white hair beckons to you both. He’s dressed in white, down to the suspenders and Crocs. He invites you into his home, and because you are on a road trip and open to serendipity, you go.
The walls are hung with watercolors of two-masted schooners, yachts, and seascapes, many of them painted on maps. Tables are piled with framed and loose artworks; a vintage Louis Vuitton case stands open so visitors can rifle through the paintings.
The artist’s name is Corrado Cohen Luria; he was an exporter in Milan but retired to Portofino 20 years ago to sail and paint. The maps are old nautical charts on which you can still see pencil marks.
Cohen Luria’s studio looks out onto the harbor, which he’s sketching with a chunk of charcoal. He still sails, he says, but only with his sons. One shelf holds a cluster of trophies from regattas “and also some waterskiing from when I was a boy.”
Looking to get away from the crowds and Ferraris, the next morning you hire a water taxi to visit a nearby beach. As the boat pulls out of the harbor, the captain, cigarette in hand, points out Dolce and Gabbana’s blue-shuttered stone house. T
he small cove of San Fruttuoso’s five restaurants can be reached only by water— the best, the captain says, is Da Giorgio, but it’s “closed because the daddy died yesterday— infarcto,” at which he pounds his chest with his fist. You eat at Da Giovanni, overlooking the beach.
There is grilled scampi and steamed mussels and a caprese with pillowy slices of mozzarella, and you wash it all down with a local vermentino. It tastes entirely of its place: crisp and light as it scrubs the salty seafood from your lips.
You are grateful, as the Nugget chugs into Piedmont, for the scenery change. Compared to Tuscany, the weather is gloomier and the hills have an austere geometry, each one topped by a stone castle above ribbons of vineyards. Langhe, about an hour south of Turin, is the land of Barolo, that grandest of Italian reds made from nebbiolo grapes, which droop from their hangman scaffolding.
The castle at Serralunga d’Alba sets the tone—the 14th-century fortress once fended off invaders with a drawbridge over a pit of sharp lances and windows through which boiling urine was poured onto enemies. The hill towns are empty, with narrow streets of béarnaise-colored buildings and Alpine-style clock towers.
Serralunga d’Alba castle
You visit Poderi Gianni Gagliardo in La Morra, one of the region’s older winemakers. Gagliardo himself, an avuncular man in a Polo shirt, tours you through his spartan cellars. He explains that because of the way land is divided among heirs, the wineries in this region tend to be a patchwork of smallish plots.
This is long-game winemaking—aged 18 months in the barrel, then in bottles for a total of 36 months, itis designed to be drunk at least a decade later. In a small tasting room, you try nebbiolos and young Barolos; the dark and spicy flavors and sharp tannins conjure cool weather and braised meat.
You wonder about the taste of a mature Barolo, the way it’s meant to be drunk without entirely meaning to, you pipe up. Kara shoots you a look that says, That’s a $250 bottle of wine.
Gagliardo considers your challenge, then softens and sends his sommelier to fetch a bottle. She returns with a 2005 Reserve, which smells like freshly cut wood and tastes faintly of blackberries. If wine is about expectation, this exceeds it. Kara, at least, looks happy.
In Piedmont you have, finally, the first truly epic meal of the trip, at Trattoria della Posta. If the homey yet elegant farmhouse restaurant—with its terra-cotta floors and white tablecloths with crocheted doilies—looks familiar, it should: It has appeared in film. But as you and Kara have established, avoiding the expected isn’t always the smart move.
Trattoria della Posta restaurant
When you arrive, a heavyset nonna in a navy dress is sitting in the front hall. You have a chopped veal tartare, thinly ribboned tajarin pasta with veal ragout, and braised rabbit—along with a bottle of young nebbiolo from a couple of towns over. “Is it good?” the waiter asks each time he comes over. You notice the shoulders on his wiry frame pulled back in a dancer’s posture.
The elderly Italian couple next to you is celebrating a birthday. You don’t say much, and neither does Kara, which feels comfortable now after six days, the way the best friendships cross a line at some point into wordless ease. You think about how this is what you’d come for—and how you might have missed it if you’d been more clever in your planning.
So what if it’s just the way you imagined it?
It’s not about the Destination
Planning Your Route
We flew into Rome and out of Turin, but you could just as easily (if more expensively) fly into Florence or Pisa and rent a car at the airport. Along the way, we decided to skip the cities (Siena, Pisa, Genoa) in favor of hopping—perhaps too ambitiously— between small towns.
Tuscany and Liguria can get extremely crowded in July and August, so spring and fall are your best bets.
Many of the medieval hill towns in the Val di Chiana (Cortona) and Val d’Orcia (Montepulciano, Pienza, Montalcino) are 20 to 40 minutes apart by car. While that may not seem like much, negotiating the narrow, winding roads and aggressive Italian drivers, especially at night and after some wine, can be stressful.
We started outside Cortona at Villa Loggio, the nine-room, German-owned vineyard-hotelina Tuscan – estate with minimalist, white-slipcovered interiors (they also run a small tasting room).
Then we moved west to La Bandita Townhouse, a chic boutique property in the perfectly preserved Renaissance town of Pienza (between Montalcino and Montepulciano), with an open- kitchen restaurant and a convivial common room filled with vinyl records, books, and an honor bar.
While in the area, detour to the hot springs at Bagno Vignoni: an unmarked dirt road one kilometer outside of town takes you to a cluster of mineral pools where you can steep while overlooking a lush valley.
Around Montepulciano there are several producers serving the region’s namesake wine; we stopped at Icario, a loft like, art-filled space, to taste its sangiovese-based reds.
Any number of local trattorias serve Tuscan classics like bistecca fiorentina and pici with wild boar sauce, but you’ll be well fed at the nostalgically rustic Osteria del Teatro in Cortona, or Locanda al PozzoAntico, off the plaza, for tasty home-style cooking.
Sette di Vino in Pienza (try the spectacular white-bean soup) has tables in a tiny piazza; in Montalcino. Drogheria Franci does a delicious risotto with pumpkin or local white truffles, and Locanda Demetra is an old cowshed turned cooking school/ restaurant that uses produce grown on property.
Driving from Montalcino, you’ll know you’re near the sea when the landscape turns quasi-tropical. At the tip of a peninsula, Punta Ala has a boat-dotted harbor and several largely indistinguishable beach clubs that, for 30 to 60 euros, will let you rent a chair and towel for the day.
From there, head north an hour to the medieval hamlet of Bolgheri, approached via the stately cypress- lined avenue that runs right into the fairy-tale-turreted Bolgheri Castle.
Inside the town’s walls you’ll find cafes and chic shops like Acqua di Bolgheri, also a fragrance made from regional botanicals, and Villa Toscana, which carries a smart selection of cashmere and handicrafts, like olive-wood cutting boards.
The store owner runs the charming antiques-and-toile-filled B&B where we stayed in nearby Bibbona, La Locanda di Villa Toscana, though the area has many small 3- and 4-star hotels. This is your base for visiting the wine house of Ornellaia for lush Super Tuscans, by appointment Monday to Friday.
Portofino is nearly three hours from Bolgheri, so we broke up the drive with a stop in Lucca, a gorgeously and historically layered, walled city with a pedestrian-only center ideal for exploring the old Roman amphitheater (now a cafe-lined piazza) and a multitude of churches and shops, as well as the house museum of Giacomo Puccini, whose Steinway is on display.
The coastal drive into Portofino is hair-raising, with narrow, twisting roads that require skillful coordination with oncoming traffic. The dreamy Belmond Hotel Splendido is on a steep hill overlooking the harbor—the outdoor dining room has a staggeringly good view. Once there, you can ditch your car for the hotel’s shuttle.
We had excellent fritto misto at Ő Magazin by the harbor; Puny is ideal for people (and boat) watching. Don’t miss the nightly show back up at the Splendido, when Vladimiro the pianist (and sometimes Antonio the bartender) gets the crowds singing and dancing past midnight.
For the 30-minute trip to San Fruttuoso for lunch and a swim, we rented a water taxi from Giorgio Mussini for 150 euros an hour.
To manage the nearly three-hour trip north to the Langhe region of Barolos and barbarescos, consider a pit stop in Ovada, whose old center is a model of colorful Genoa-republic architecture, and Acqui Terme, a sulfur hot springs town with a Gothic cathedral.
Or, if you’re pressed for time, take the autostrade directly to Serralunga d’Alba, a mountain town topped by a 14th-century unfurnished castle with a chilling “well of torture” (at one time, a pit filled with swords) and a stunning view overlooking valleys of vineyards.
From the summit you can see the nearby hill town of Castiglione Falletto: a little farther out is Grinzane Cavour, with an engaging castle museum of winemaking plus an in-demand enoteca.
There are a number of small properties and B&Bs in the area, but the 18th-century Hotel Villa Beccaris in Monforte d’Alba stands out for its pool and private park.
We had our most memorable meal at the family- owned Trattoria della Posta (you’ll need to book a reservation, through firstname.lastname@example.org); as an aperitivo, try the pink sparkling wine from Parusso, made from nebbiolo grapes.
Also worthwhile is La Cantinetta in Barolo, which serves an excellent panna cotta. Poderi Gianni Gagliardo in La Morra runs a one-table dining room in a converted farmhouse that can be booked for simple or multicourse meals, accompanied by tastings of the producer’s elegant nebbiolos and Barolos.
For Help Getting it Done
We traveled with an assist from Arblaster & Clarke Wine Tours, a 31- year-old, Salisbury, England-based company that maintains a deep network of wine producers and unique properties throughout Italy (and beyond); they’ll arrange cellar visits and activities that include truffle hunting and cooking classes.