Cypress-lined hills near the town of Panzano, in Chianti.

Andrea Wyner

The culinary pleasures of Italy's iconic region somehow taste even better when you’re in the driver's seat. Here's how to take the perfect week-long road trip.

David Amsden
January 17, 2018

As I pressed the ignition button on my white Vespa, I found myself seized by panic. My heart beat like a jackhammer, and a faint tremor crept into my fingertips. Judging from the facial expressions of my girlfriend, Stephanie — raised eyebrows, pursed lips — it was clear that she, too, was battling jitters as she fired up her own Vespa, a contrasting cherry red.

What on earth had we gotten ourselves into?

We were in a parking garage on the outskirts of Florence, readying ourselves for a six-day road trip in search of the sort of divine culinary experiences Tuscany is so famous for. Zipping from town to town, from enoteca to trattoria, we would sample the gooiest stracciatella, the boldest Brunellos, the lardiest lardo. In other words, we would do what everyone comes here to do — be gluttons — but the Vespas would lend an air of spontaneity to our travels. No set departure times, no prebooked hotels. We'd ride until we felt like stopping, crashing at the most convenient, comfortable inns we could find.

Vespas, manufactured in the Tuscan city of Pontedera since 1946, offer an adrenalized and accessible way to absorb, rather than merely navigate, your surroundings — something I discovered nearly a decade ago when I rode one for the first time in Rome and became an immediate convert. To Americans accustomed to SUVs, crowded interstates, and the notion that only leather-clad outlaws can travel on two wheels, the idea of using a scooter for a longer excursion might seem ludicrous. But mention it to a European and you'll get a shrug and a grin — a bit goofy, sure, but perfectly reasonable. Vespas are powerful enough to handle twisty back roads, less intimidating than motorcycles, and preposterously fuel-efficient. What better way to infuse our journey with a dose of authenticity and adventure?

That, at least, was the fantasy. Reality, that stubborn scourge, intervened on our first morning with a tempestuous thunderstorm — the reason for our ragged nerves. Our departure was delayed by hours, throwing a wrench into the itinerary we had roughly sketched out with the help of Francesco Venzi, the amiable owner of Central Italy Motorcycle Tours, the local outfitter that had supplied us with the scooters. Though the rain eventually subsided, the roads were slick and the air was frosty as we crossed the Arno, making our way south into the storied hills of Tuscany.

The medieval town of Pietrasanta, in Tuscany.
Andrea Wyner

Twenty minutes into our ride, it started to pour again. On the famous Via Chiantigiana, with its corkscrew climbs through stands of cypress, I found it next to impossible to savor the open vistas. By the time we pulled into Greve in Chianti, the hub of the local wine industry, I was cursing myself for not having packed rain gear and again questioning our overall sanity. We came to a stop in the main square, a quaint, triangular plaza teeming with flower vendors, restaurants, and tasting rooms. Though drenched and exhausted, Stephanie and I both were also grinning, the absurdity of the situation causing us to break into fits of laughter.

Our goal had been to end the day in Pienza, 2 1/2 hours farther south. "Um, not happening," Stephanie declared, reminding me that the point of this trip was to make it about the journey, not the destinations. Rather than see the rain as a hindrance, we opted to think of it as a kind of guide, one that at the moment was telling us to call it a day. We checked in to the Albergo del Chianti, a no-frills hotel on the plaza, and set out for some food and drink.

From left: Grilled octopus at Babazuf, a trattoria in Siena; Siena’s Palazzo del Campo.
Andrea Wyner

To the untrained eye, every restaurant in Tuscany looks more or less identical — making it a challenge to discern between those pandering to tourists and those committed to tradition. Our dinner that night was a bland, caloric bust, but another experience more than made up for it. Earlier in the evening, we'd visited Diversus, a nondescript wine bar and restaurant, simply because it was on the ground floor of our hotel and a glass of wine, any glass of wine, would be a godsend after our discombobulating day. As soon as we sat down, we were approached by an affable gentleman who introduced himself as Bernard Buys, the co-owner of the establishment as well as Le Muricce, a nearby vineyard.

"What sort of wines do you like?" he asked.

"Alcohol-forward?" I ventured.

Either ignoring or failing to register my attempt at humor, Buys spent the next hour regaling us with stories. Belgian by birth, he discovered a love of wine in France and now lives in Tuscany during the harvest season. He spoke of picking grapes in a paternal tone bordering on the religious. All the while he poured us tastes from various bottles not available in the United States: a tart Sangiovese, a ruby-red Chianti Classico, and a supple Merlot, each complemented by plates of exquisite cured meats and cheeses. By the time we ambled back out onto the square, our day's misadventures had become a distant memory.

Cheese and charcuterie at Il Bacchino, a restaurant in Massa Marittima.
Andrea Wyner

The next morning, we rode southwest toward the seaside province of Grosseto, an area long popular with Europeans but still largely undiscovered by Americans. Not that we were trying to be pioneers. Grosseto promised clear skies, so that's why we picked it. Any doubts I had about the Vespas were obliterated as we zigzagged through vineyards, forests, and cliff-side villages where wizened old Italians waved at us. As I felt the intoxicating sense of freedom and a visceral communion with the landscape, I realized you simply can't experience a destination the same way from the hermetic womb of an automobile.

We stopped for lunch in the medieval city of Siena, where our Vespas easily navigated the catacomb-like streets, and pulled up right in front of a thimble-size trattoria called Babazuf. We'd chosen it via the indispensable mobile app of Osterie d'Italia, an annual guide that highlights largely traditional restaurants that adhere to Slow Food philosophies. We could hardly say a word, reduced to monosyllabic grunts by a spread that included a delicate eggplant tart; weightless, multicolored gnocchi improbably dense with flavor; and a hearty, intricately spiced lamb stew.

As we rode onward, hills and woodlands open-ed up to verdant flats, a glittering coastline, and, eventually, Castiglione della Pescaia, a Mediterranean town surrounding a historic harbor. We stayed at Riva del Sole, a lovely full-service resort where we drank Prosecco on the beach as the sun dipped below the horizon, painting the wispy clouds with brushstrokes of lavender and tangerine. After scootering our way into the town center, we dined at La Fortezza, a tavern tucked in an ancient fortified wall. I'd never thought much about seafood being part of Tuscan cuisine, but after devouring the restaurant's signature dish — a gigantic platter of freshly caught lobster served over handmade tagliolini — I will now.

From left: Lunchtime at La BotteGaia, a restaurant in Pistoia; the cathedral in Massa Marittima.
Andrea Wyner

Over the next few days we rode north, navigating our way through fields of red poppies, taking tight switchbacks through classic hilltop towns like Volterra, and finally reaching Lucca, which we used as a base for the next two days. Having become comfortable with the scooters, we pushed the motors with a ride into the steep Apuan Alps, where we skirted high peaks and dozens of marble quarries before making our way down the mountains and into Pietrasanta, an artsy coastal town. There, on the advice of a local, we slipped into a café called Libero for lunch. At this modern take on a traditional trattoria, we made a meal out of various small plates: steak tartare, Camembert crostini, a heaping platter of various crudi. A buffet of the simplest flavors had been mysteriously elevated, in what we'd come to see as the trademark of Tuscan cooking, to high art. Before we knew it, we were the only ones there, unaware that the restaurant had closed an hour earlier. The owner didn't seem to mind. After we'd paid the bill, he poured us two glasses of grappa and treated us to an impromptu seminar on Tuscan olive oils. We learned why olives must be pressed soon after harvest (to avoid oxidation), why the oil is bottled in dark bottles (to keep sunlight out), and how, as with wine, you wanted to use light, silky olive oils for fish and spicy, throat-scratching varieties for meats.

The following day, we'd be heading back to Florence, but for the moment that seemed like an eternity away. Leaving the restaurant, the sun was still shining, the Vespas beckoning.

"Where to next?" Stephanie asked.

"Who knows?" I replied.

How to Rent and Ride a Vespa

Find a Local Outfitter

Florence-based Central Italy Motorcycle Tours will map out a manageable route; a rental costs $220 to $350 per week. Novices can do this trip, though it's smart to take a practice spin (or two) at home.

Pack Light

A carry-on-size duffel is the way to go, since it can rest comfortably between your feet while riding. A small satchel with valuables can be stowed in the lockable compartment under the seat.

Drive Safely

On country roads, you are subject to the same rules as cars, but in some towns and cities you can take a Vespa onto streets that are off-limits to automobiles. Parking is a cinch: as long as you're not blocking traffic, you're good.

Dress Right

A jacket, ideally waterproof, is a must for protection and warmth; ditto a pair of long pants and leather gloves. A pair of earbuds will help block out wind noise (though by law you can cover only one ear).

Eating Your Way Through Tuscany

Check out these restaurants, which the writer made a part of his itinerary.

Babazuf: Tucked away on a street near Siena's central plaza, this osteria is famous for its delicate house-made pastas — particularly the five-colored gnocchi and tagliatelle with black truffles. Entrées $8–$21.

Il Bacchino: Don't bother reading the menu at this tiny enoteca in Massa Marittima. Just ask the owners to bring you their best local cheeses and cured meats. 8 Via Moncini; 39-0566-940-229; small plates $4–$11.

Diversus: At this warm and friendly spot on the central plaza in Greve in Chianti, owner Bernard Buys pairs his vast selection of Tuscan wines with exquisite cured meats. Entrées $12–$22.

La BotteGaia: This osteria in Pistoia serves flavorful, hearty dishes like duck macaroni and artichoke tart in Parmesan sauce. Try the lardo, sliced paper-thin and illicit with flavor. Entrées $10–$16.

La Fortezza: Seafood takes center stage at this trattoria built into the ancient fortified wall that once protected Castiglione della Pescaia. The signature lobster over tagliolini is a must. Entrées $14–$45.

Libero: With a menu heavy on the freshest of local ingredients and small plates (platters of crudi, various crostini), this restaurant embodies the relaxed, creative spirit of Pietrasanta. 16 Via Stagi Stagio; 39-0584-790452; Entrées $9–$19.

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