Inside Two Dreamy Tuscany Hotels
Some places lived in your imagination long before you ever arrived. For me, Tuscany was one of them. At the beginning of the year, I had even pinned a photo of the region to my vision board—its stone villages had been etched in my memory for years. Despite countless trips to Italy, I’d somehow never made it beyond the cities and coastlines into the countryside I’d always dreamed of. So when a free week appeared in my spring schedule, I took it as a sign. My friend, Anh-Thi, and I booked a flight to Pisa, reserved a rental car and mapped out seven days of hilltop citadels, vineyard lunches and winding roads through olive groves. Along the way, we stayed at two dreamy Tuscany hotels.
Here are the highlights of my Tuscan escape:
On the Road through Chianti
The journey began once we left Pisa. Within 30 minutes, the scenery had started to change: the city gave way to rolling hills, cypress trees lined the winding roads and stone villages rose in the distance. From Siena’s medieval hilltop, a tower stood clearly against the sky. Tuscany felt bigger than I had ever imagined.
A Castle in the Hills
By the time we arrived at COMO Castello Del Nero, the late-afternoon sun was casting everything in gold. The drive up to the castle felt straight out of a film: a winding gravel road lined with sentry-like cypresses, rolling vineyards stretching into the distance. At the top of the hill, the centuries-old estate had slowly come into view. After the long drive, being welcomed with a glass of Prosecco at the entrance felt almost too perfect.
We were shown to our room in the quiet annex just behind the main castle, with the Tuscan hills feeling like they were ours alone to take in. Inside, the space felt airy and serene, with high ceilings, exposed wood beams and cool terracotta floors dating back to the 12th century. Immediately, I could feel everything slow down. Outside, I spotted sunbeds beside the pool and manicured gardens, while the air carried the scent of rosemary and lavender. We spent the afternoon poolside, soaking in the views beneath classic parasols.
Meals at the castle were just as spectacular. At Pavilion, we lingered over long alfresco lunches of caprese salad, warm focaccia and pici pomodoro, the thick hand-rolled pasta Tuscany is known for, while the hills glowed in the background. One evening, we settled in at La Torre, the hotel’s Michelin-starred restaurant, for a multi-course tasting menu centered on produce from the estate’s gardens, local meats and freshly caught seafood. Each course took its time, paired with Tuscan wines, as the sky faded beyond the castle walls.
A Day Between San Gimignano and Siena
The castle also became our base for exploring the surrounding countryside. One of our favorite adventures led us to San Gimignano, where medieval towers rose above the hills like something from another century. Then it was on to Siena—this time not just a passing glimpse from the road, but a chance to wander its narrow streets properly, moving between a handmade pasta lunch at Grotta Santa Caterina da Bagoga (finished, of course, with the most delicious tiramisu) and tiny wine bars like Vineria Tirabusciò tucked into stone alleyways. But no matter where the day took us, the best part was the drive back to the castle on the hill.
A Tuscan Village of Our Own
Continuing deeper into the Tuscan countryside, we made our way to Borgo San Felice Resort, our second home base of the trip, and a place that had been on my bucket list. Unlike anywhere I’ve stayed before, the property was an entire Italian village reimagined as a spectacular hotel. Wandering through the stone pathways for the first time, it felt like stepping back in time, as though I’d stumbled into another era. Former homes, a tiny church, the old schoolhouse and the village piazza have all been transformed into guest rooms, restaurants and the spa.
Before long, our days revolved around the village itself. At San Felice’s winery, 18th-century cellars held rows of aging bottles beneath vaulted stone ceilings, and we spent hours moving between wine tastings, vineyard walks and a tiny museum filled with century-old vintages. Afterwards, we made our way to the glass-like pool, where afternoons were reserved for little more than sunbathing with views over the valley, followed by a cocktail at the poolside Bar Archi.
Meals became part of the experience, too. We started each morning at Poggio Rosso over flaky pastries, fresh fruit, artisan breads and cappuccinos that somehow tasted even better with vineyard views. The Michelin-starred restaurant then transformed for the evening. We opted for the four-course dinner: local dishes with a modern twist, bold flavors and artfully plated, including the tender wagyu beef, mushroom risotto and airy focaccia bread.
One Postcard After Another
When we weren’t wandering the village-like property, we spent our days in the Tuscan countryside. One of the most memorable drives took us to Pienza, where winding roads opened onto postcard views before arriving in the tiny Renaissance village perched above the Val d’Orcia. We wandered quiet lanes, stopping for fresh pasta at Trattoria da Fiorella and scoops of gelato from Buongusto, which we enjoyed on Piazza Pio. We then took in an endless patchwork of landscapes, stitched together in every shade of green. Standing there, looking out across the region I had dreamed of visiting for years, Tuscany suddenly felt both exactly how I had pictured it and somehow even better.
The Road Home
By the end of the week, Tuscany was no longer pinned to a board or held in imagination. It had become something I had actually lived, and would dream about for a long time to come. As we drove back to Pisa, I kept looking out at the scenery, trying to hold onto it just a little longer.
