Enchanting Tuscany: A Journey Through Hills and Vineyards

Some places lived in your imagination long before you ever arrived. For many, Tuscany is one of those enchanting locations that captures the heart and soul. With its rolling hills, picturesque vineyards, and timeless stone villages, it’s easy to see why I pinned a photo of Tuscany to my vision board at the beginning of the year. Despite multiple trips to Italy, I had never ventured into its countryside, a dream long held. So when a week appeared in my spring schedule, I could only take it as a sign. My friend Anh-Thi and I booked a flight to Pisa, reserved a rental car, and planned a week filled with hilltop citadels, vineyard lunches, and winding roads through olive groves. Along the way, we stayed at two dreamy hotels that made our adventure unforgettable.

On the Road through Chianti

Our journey began as we drove away from Pisa. Within a mere 30 minutes, the scenery transformed from urban grit to stunning landscapes. The city gave way to rolling hills where cypress trees lined the winding roads and stone villages emerged on the horizon. As we approached Siena, the medieval tower stood tall against the sky, reminding me that Tuscany was even grander than I had ever imagined.

A Castle in the Hills

Arriving at COMO Castello Del Nero, the setting sun bathed everything in a golden hue. The route to the castle was a film-like experience—a winding gravel road bordered by imposing cypresses and sweeping vineyards. Finally, the centuries-old estate came into view. After our long drive, being greeted with a glass of Prosecco felt truly serene.

We were escorted to our room in the tranquil annex behind the main castle. The Tuscan hills seemed to stretch endlessly, feeling like our own personal paradise. Inside, the airy room featured high ceilings, exposed wood beams, and cool terracotta floors that dated back to the 12th century. Instantly, I felt time slow down. Outside, sunbeds awaited beside the pool, and the air was fragrant with rosemary and lavender. Our afternoon was blissfully spent poolside, soaking up the sun beneath classic parasols.

Meals at the castle exceeded all expectations. At Pavilion, we relished long alfresco lunches of caprese salad, warm focaccia, and pici pomodoro (a thick hand-rolled pasta unique to Tuscany). One evening, we dined at La Torre, the hotel’s Michelin-starred restaurant, where we indulged in a multi-course tasting menu, showcasing produce from the estate’s gardens paired with exquisite Tuscan wines.

A Day Between San Gimignano and Siena

The castle also served as our hub for exploring the breathtaking countryside. One day, we ventured to San Gimignano, where its medieval towers rose against the hills like a scene from a storybook. Afterward, we turned our sights to Siena, this time not merely passing through but wandering its narrow streets. We enjoyed handmade pasta at Grotta Santa Caterina da Bagoga and topped off our meal with the most delicious tiramisu. What remained most etched in my mind was the enchanting drive back to the hilltop castle.

A Tuscan Village of Our Own

Continuing deeper into the Tuscan countryside, we arrived at Borgo San Felice Resort, our second shared home. Unlike any place I’d ever stayed, this property snatched my breath away; it was an Italian village reimagined as a spectacular hotel. As I strolled through its stone pathways, I felt as though I had stepped back in time. Former homes, a tiny church, an old schoolhouse, and a village piazza had been transformed into delightful guest rooms, restaurants, and a spa.

Before long, our days became immersed in village life. At San Felice’s winery, we discovered 18th-century cellars filled with aging bottles beneath vaulted stone ceilings. Hours melted away as we moved between wine tastings, vineyard walks, and exploring a delightful museum filled with century-old vintages. Our afternoons were best spent at the stunning pool, where sunshine and valley views created a slice of paradise.

Every meal at Borgo San Felice was an experience in itself. Each morning began at Poggio Rosso with flaky pastries, fresh fruit, artisan breads, and cappuccinos that tasted even better with vineyard views. Dinners transitioned into four-course affairs, combining modern twists on local flavors, including tender wagyu beef, mushroom risotto, and airy focaccia bread.

One Postcard After Another

Our exploration didn’t stop at the village. We spent our days traversing the stunning Tuscan countryside, with one of our most memorable drives leading us to Pienza. Winding roads unveiled breathtaking postcard views, culminating in a quaint Renaissance village perched above the Val d’Orcia. We roamed through quiet lanes, enjoying fresh pasta at Trattoria da Fiorella and scoops of gelato from Buongusto, savored on Piazza Pio. The scenery unfolded into an endless patchwork of landscapes, showcasing every shade of green. Standing there, gazing out at a region I had long envisioned, Tuscany felt both exactly as I had imagined and surpassingly better.

The Road Home

As our enchanting week drew to a close and we returned to Pisa, Tuscany had transformed from a mere pinned image to tangible memories I would cherish forever. Each glance out at the rolling hills during our drive home was an unending reminder of this beautiful land.

About the Author

Shelbi Okumura is a San Francisco-based content creator who has traveled to more than 55 countries around the world. Follow @bucketlistbums for her adventures, travel guides, and wanderlust inspiration.

This immersive journey through Tuscany is just a glimpse of the beauty and allure that awaits in one of Italy’s most celebrated regions.