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Wandering Chef: Fabio Viviani in Amsterdam

When a couple embarks on a spontaneous road trip through Italy, they rediscover the joys of unplanned adventure.

Active from the 13th to 15th centuries and considered an influence on the pre-Renaissance movement, the Sienese School of painting is identifiable by its themes—always religious, and usually with a focus on Biblical miracles—and its signature style, a dreamy mix of Roman, Gothic, and Byzantine influences that often feature dazzling gold backgrounds. Opened in 1932, this museum boasts one of the world’s largest collections of Sienese School works, as well as a number of Renaissance and late-medieval pieces from Italian artists. Wander through the impressive building—a combination of two 14th- and 15th-century noblemen’s palazzi—to find works like Duccio’s Madonna and Child, Michelino da Besozzo’s Mystical Marriage of Saint Catherine (celebrating the “calling” of Siena’s native daughter), and Bartolo di Fredi’s expansive Adoration of the Magi. Paired with a visit to Florence’s Uffizi, coming here offers insight into the differences—and longtime rivalry—between the two cities.

Founded in the 9th century, Santa Maria della Scala was one of Europe’s first hospitals. It was also one of the first hospitals anywhere to disinfect its equipment and only stopped taking in patients in the 1980s. (The writer Italo Calvino died here in 1961.) The early history of the hospital is illustrated in the 15th-century frescoes decorating the walls of the Pilgrim’s Hall, and there is a fascinating archaeological museum housed in the labyrinthine basement rooms.

Just behind the Pantheon hides the church of Santa Maria Sopra Minerva, a gem in its own right. The only Gothic church in Rome’s center, it’s a breath of fresh air from over-the-top Baroque opulence. Plus, it has gorgeous frescoes by Filippo Lippi (an early Renaissance master), the body of Italy’s patron saint Catherine of Siena, the tomb of painter Fra Angelico, and a statue done—at least partly—by Michelangelo himself.

The Maremma region of southern Tuscany, about an hour south of Siena, is an area of olive groves, wooded valleys, and ancient legends. One such tale, dating from the days of the Etruscans and Romans, chronicles an epic battle in which Jupiter threw lightning bolts at Saturn—and missed. As the story goes, when the bolts landed on the ground, they formed the bubbling hot springs now known as the Terme di Saturnia. Full of therapeutic minerals, the hot springs feed a variety of pools throughout the valley that have warmed and healed centuries of bathers. Today, you can soak up the goodness at the luxury Terme di Saturnia Hotel & Spa, which offers therapies performed with the waters, or at a free public bathing spot. To find the main one, head down a dirt path just outside of town, past a parking lot and changing area, until you spy a waterfall feeding a series of natural pools, each turned white by the mineral-rich water.

There is a reason why renting a villa in Tuscany is so popular - rustic farmhouses, rolling hills filled with olive and plum trees, golden sunsets, locally-harvested wine, creamy cheeses, and cool evenings spent with friends and family. Renting a villa provides a relaxing base for your sightseeing in the region. Almost all Tuscan towns allow easy day trips to the main sights: - Florence‘s art and Renaissance history (Duomo, Uffizi Gallery, Michelangelo’s David) - Cortona’s steep, narrow streets and medieval walls - Siena’s cultural city center, now a UNESCO World Heritage Site - San Gimignano’s fortified towers set amidst picture-perfect Tuscan hillsides - Montelpulciano’s world-famous wineries and more This offers the best of both worlds - after a dusty day of sightseeing, you can relax at your villa with a jump in the pool and a glass of wine. Watch the sun go down in a purplish haze, unwind with friends, and enjoy the lovely moment. I recommend YourTuscany.com, which is where we found Villa Coloniale (above) in the town of Pergine Valdarno. The infinity pool and covered patio are guaranteed to put you in a relaxed, Italian frame of mind!

For nearly three centuries, workers serving the nobility at Castello Banfi in Tuscany lived in a small hamlet within the castle grounds. In 2007, however, the stone houses within their tiny village were completely renovated under the direction of Italian interior designer Federico Forquet, catapulting Castello Banfi into a new era of grandeur. Today, the property welcomes guests from November through March in two guest rooms and 12 suites, each with wood-beamed ceilings, countryside views, and bathrooms stocked with “vinotherapy” products made from the estate’s Sangiovese Brunello. A central garden with a pergola, a heated outdoor pool, secluded lounging spaces, and alfresco massage tents offer plenty of ways to take in the surrounding vineyards. If you’re feeling more active, take a cooking class with the chef (held a short drive away at the estate farmhouse), tour the Banfi winery, or venture out to nearby historic towns like Montalcino and Siena.

Giovanni di Piero Antinori became a member of the Florentine Winemakers Guild in 1385—and his descendants have been in the business ever since. Today, the company is overseen by Marchese Piero Antinori—the 25th generation of the titled family—and his three daughters, all of whom were involved in the seven-year project to build this stunning winery and visitors’ center. With a contemporary design crafted with materials like wood, terra cotta, and weathered steel, and featuring views out onto vineyards lush with classic Chianti grapes, the center houses a museum and art gallery, winery and cellar, shop, and rooftop restaurant serving gourmet pairing menus. Four different types of tours are available, ranging from general overviews tailored to the first-time guest (and including tastings of three signature wines), to more in-depth cellar visits (with upgraded cru tastings) and tailor-made experience for connoisseurs.

Gain rare access to the region’s time-honored traditions and meet local families during this exclusive journey.

Take cooking classes in Umbria, explore a medieval fortress in Spigeto, visit Rome, and more on this food-and-culture filled Italy travel itinerary.