THEN: Castello di Casole (1960s) has been in existence in one form or another for some 300 years.
Courtesy Timbers Resorts

A small window provides views of the rolling landscape, and from my perch I can see the distant spires of Mensano, an ancient hamlet located about five miles away. I feel like a princess, locked away in this castle as I am, and I toy with the idea of unfurling my hair to see if anyone climbs up. Then I remember the poacher.

My tower room is one of the hotel’s several lodging options, which range from apartment-style suites to rustic villas, all furnished with Tuscan antiques, plush sofas and chairs, sumptuous bed linens and cavernous marble bathrooms with deep tubs for soaking in (and, if you’re like me, drinking wine in). Just throw in some courtesy bath salts and you’ve got yourself a party.

For those needing a larger or more sumptuous space, there’s the three-bedroom Bargagli Penthouse, named in honor of the aristocratic family who owned the estate and ran a farm here in the 1800s. More than 350 people lived and worked on the farm, residing in the outbuildings and farmhouses that since have been painstakingly restored for rent or ownership (partial or full).“It was one of the most significant agricultural compounds of its time,” says Ross, who oversaw the hotel’s six-year renovation.

The Bargagli family’s private crypt remains on the property, and one morning, Ross lends me the key to peek inside. There’s a small altar and a domed ceiling made of blue mosaic tile. It’s not at all spooky, and I wonder if Visconti ever partied in here while he owned the estate. It seems unlikely, but the nearby vaulted wine cellar was surely treasured real estate.

The former wine cellar is still a popular place for those in need of respite, as it is now home to the Essere Spa. Many of the treatments and potions offered here are inspired by the Tuscan countryside and include lemon, fresh rosemary and olive oil. The Grape Seed Massage for the face and body proves just the ticket after a long trans-Atlantic flight.

If you run out of things to do on the premises, the resort also offers tours of nearby wineries (there are plenty to choose from) as well as guided excursions to Siena and the glittering city of Florence, where we head on the final day.

The birthplace of the Renaissance, Florence is home to Michelangelo’s David, the famed Uffizi Gallery, the Duomo and other fabled basilicas, churches and pieces of art. It’s also a hub for Italian fashion, with high-end boutiques lining the cobblestone streets. Stalls selling leather goods, scarves and souvenirs are everywhere.

After a full day of shopping and sightseeing, we head to the Grape Harvest Festival in Mensano, whose skyline I could glimpse from my tower window. It’s here that I have my final glass of wine on the trip. The night is clear and cool, and the medieval town glows in the flickering light of electric lanterns. Sitting on a stone wall, I stare into the dark valley and quaff a peppery varietal, holding the dram in my mouth for a few seconds to savor the magic.

It’s then that I hear a rustle in the leafy distance and peer into the darkness with sudden sobriety. Could it be the elusive ­cinghiale? Perhaps it is merely my imagination, riffing on a morning memory in Tuscany­ that already is etched deep in my bones.

Kathleen Parrish, a frequent American Way contributor, is a freelance writer from Bethlehem, Pa.