Trotting Through Tuscany with Italian Cowboys

  • A buttero getting ready for a ride at the Azienda Regionale Agricola di Alberese.

    A buttero getting ready for a ride at the Azienda Regionale Agricola di Alberese.

  • A view from the ramparts at Castiglione della Pescaia.

    A view from the ramparts at Castiglione della Pescaia.

  • A platter of salumi and cheese accompanies tasting sessions at L'Andana's winery.

    A platter of salumi and cheese accompanies tasting sessions at L'Andana's winery.

  • Massimo Brilli's lone beachside kiosk at Cala Violina produces terrific food like ricotta-stuffed tortelli.

    Massimo Brilli's lone beachside kiosk at Cala Violina produces terrific food like ricotta-stuffed tortelli.

  • Trattoria Toscana's country-style dining room.

    Trattoria Toscana's country-style dining room.

  • A cut of Maremmana beef at Trattoria Toscana.

    A cut of Maremmana beef at Trattoria Toscana.

  • The tree-lined driveway that leads up to L'Andana.

    The tree-lined driveway that leads up to L'Andana.

  • L'Andana chef Gianluca Bennardo.

    L'Andana chef Gianluca Bennardo.

  • Rounding up cattle at the Azienda Regionale Agricola di Alberese.

    Rounding up cattle at the Azienda Regionale Agricola di Alberese.

  • Vineyards at the Le Mortelle estate.

    Vineyards at the Le Mortelle estate.

  • Poolside at L'Andana.

    Poolside at L'Andana.

  • With its medieval ramparts and expansive sea views, Castiglione della Pescaia makes an excellent base for exploring this unspoiled slice of Tuscany.

    With its medieval ramparts and expansive sea views, Castiglione della Pescaia makes an excellent base for exploring this unspoiled slice of Tuscany.

  • A field of sunflowers near Castiglione della Pescaia.

    A field of sunflowers near Castiglione della Pescaia.

  • The bedroom of a suite at L'Andana.

    The bedroom of a suite at L'Andana.

  • Special saddles and long hooked canes called uncinos are among the gear used by Maremmani cowboys.

    Special saddles and long hooked canes called uncinos are among the gear used by Maremmani cowboys.

  • One of the horses stabled at Le Cioccaie riding center.

    One of the horses stabled at Le Cioccaie riding center.

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I wake up on my first day at L’Andana to orange blossom–scented air and a soft light falling on lemon-hued stucco walls. I’m raring to ride under the Tuscan sun, but unfortunately by the time I’ve finished breakfast, it’s drizzling outside. My guide from Le Cioccaie, Laura Elsaesser, and I decide to saddle up anyway.

The rain starts coming down stronger when we’re halfway up the 200-meter-high La Badiola hill. We press on to Romitorio di San Guglielmo, an abandoned 16th-century chapel, before entering the woods that will take us down the other side of the rise. The air is nippy and filled with the woody smell of decaying autumn leaves. Wherever hooves land, dry twigs crackle against the pebbly ground. Irruentox, the bay eight-year-old I’m riding, stumbles a few times on slippery rocks during our steep descent, but as we make our way to the Le Mortelle estate, the weather finally clears. There we tether our horses for a guided tour of the Antinori family’s state-of-the-art winery, finishing the morning with a wine tasting accompanied by a platter of salumi, pecorino, and crostini.

More wine awaits us after we trot back to L’Andana through olive groves and vineyards. With typical Italian exuberance, Elena Antinucci, who runs the hotel’s cellar, pours us wines from three of the four estates owned by the Morettis—Petra in the Tuscan province of Livorno, Bellavista in Lombardy, and Tenuta La Badiola right here in the Maremma. We’ve probably sampled most of the 19 labels from these vineyards by the time Laura decides she better ring a colleague to pick her and our mounts up with a horse trailer.

At Trattoria Toscana that evening, I keep the wine to a minimum in order to better appreciate the food. Though Alain Ducasse only supervises and visits twice a year now, the restaurant has kept its Michelin star under a succession of chefs, the latest being Gianluca Bennardo. The dishes of risotto with pigeon breast that a hunter brought in that morning and cured octopus from the Tyrrhenian Sea are remarkable, but what stands out most is the pappa al pomodoro, a Tuscan soup traditionally made from stale bread and tomatoes. Here it is rich, robust, and tangy. Not wishing to scandalize the posh-looking Swiss couple at the next table, I refrain from licking the bowl clean.

The next morning, I meet up with Laura at Le Cioccaie. The stables’ owner, Nello Raffi, is to take us on an eight-kilometer ride from Punta Ala to Cala Violina beach. His family has been in the Maremma for generations, and he knows the land like the back of his hand. Unlike yesterday, it’s a warm 23°C, and the horse flies are out in force. They follow us from the pine-covered promontory of Punta Ala to the beach, biting at Irruentox and the other horses all the way. When we reach the shore, Raffi points out toward the distant lump of Giglio Island, which made international headlines when the Costa Concordia cruise ship ran aground there in 2012.

There’s only one food kiosk at Cala Violina, and its owner, Massimo Brilli, knows Raffi well. Two other friends of Raffi’s, Gianni and Alessia, whom we met riding in the woods earlier, catch up with us there. The impromptu gathering grows even livelier when Gianni’s ex-wife, Claudia, who was sunbathing at the beach, joins in. The quality of the food that Brilli whips up in his small unnamed kiosk is beyond my expectations. Out come trays of large ricotta-stuffed tortelli squares drizzled with sage butter and a spread of salumi with pecorino and unsalted bread. All these are typical Maremmani food, except for the pecorino, a ewe’s-milk cheese introduced by Sardinian migrants in the 19th century. Over glasses of crisp sangiovese, the lunch stretches to three hours and enters my notebook as one of the warmest travel experiences of my life.

When we ride back through holm oak, chestnut, and cork trees, Irruentox’s gait feels lighter. It seems like I’ve won him over—perhaps because while the other riders were enjoying a post-lunch coffee, I was busy pinching horse flies off his hide. The bosky foliage provides relief from the sun while a cool breeze carries the scent of wild myrrh through the woods that have come alive with bird song. Irruentox and I are happy.

Unfortunately, I’m not allowed to ride him into Castiglione della Pescaia that evening, as the cobbled streets are still packed with the last of the summer’s holidaymakers. So I visit on my own steam, walking past alimentari shops, small jewelers, and seafront restaurants before ascending to the town’s medieval hilltop fortress to take in the sweeping sea views. After a simple dinner at a local pizzeria of schiacciata—a crisp Tuscan flatbread lightly perfumed with toasted sage—it’s time to turn in.

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