Two Birds Travel Diary: Tuscany
Tuscany’s Timeless Charm at Castel Monastero & Fonterutoli
After soaking up the intellectual elegance of Florence, we craved space—vineyards, olive trees, and a slower rhythm. Tuscany welcomed us with all of that and more: fine wine, floating in mineral pools, and even a spontaneous detour to one of Italy’s most storied cities. Here’s how this next chapter of our Italian journey unfolded.
Arrival at Castel Monastero – A Taste of Stillness
Our morning began with a private transfer to Castel Monastero, a five-star retreat tucked into the Chianti countryside. This restored monastery has been reimagined into a peaceful haven where elegance meets authenticity. If you are a fan of designer fashion, this is the perfect moment to make a stop at the famous designer outlets on your way from Florence to Tuscany. Trust me, it is well worth a stop!
Before check-in, we eased into the Tuscan pace with lunch at the hotel’s La Contrada restaurant—simple, soulful dishes enjoyed on a terrace kissed by the midday sun.
But dinner? That was something else entirely.
That evening, we dined in the Michelin-starred Cantina restaurant, nestled in the centuries-old wine cellars. It wasn’t just a meal—it was a guided experience. Our waiter didn’t serve so much as orchestrate. He introduced each course like a poem, paired each wine like a symphony, and made us feel like honored guests at the table of Tuscany herself. It was intimate, joyful, and unforgettable.
Spa Magic, Wine Royalty & a Surprise Stop in Siena
We started the day at the hotel’s acclaimed spa, where we dipped into the magnesium-rich saltwater pool. And when we say “floated,” we mean it—we could barely keep our feet on the bottom. It was like being suspended in a dream, surrounded by vaulted stone walls and utter calm - except for our fits of laughter as we tried to navigate while we bobbed around the pool.
Later that morning, our private driver picked us up for an exclusive visit to Castello di Fonterutoli in Castellina in Chianti. The estate itself felt like a step back in time: a medieval hamlet overlooking the Siena skyline, complete with its own church and charming stone homes.
We toured the impressive cellar before heading into a private tasting room for five exceptional wines—including Siepi, their crown jewel—alongside olive oil and grappa. Then came a chef-designed four-course lunch at the Osteria di Fonterutoli, perfectly paired to elevate every sip. The flavors, the view, the wine—it was the kind of meal that lingers long after the plates are cleared.
And just when we thought the day had peaked…
Our driver surprised us with an impromptu detour to Siena.
He guided us through the historic city from the comfort of the car, pointing out the Piazza del Campo, where the famous Palio horse race is held each summer. We even had time for a quick stroll into the square and a peek inside the magnificent Siena Cathedral—a stunning contrast of white and green marble with soaring Gothic arches. It was completely unplanned, and completely perfect.
Our wonderful driver giving us all of the info about the horse races.
That evening, we returned to Castel Monastero for one last peaceful night in the hills, full from both the day’s adventures and the region’s beauty.
Southbound by Train, Heart Full of Tuscany
After incredible breakfast with the most luscious fresh juices we said a farewell to our beloved Chianti countryside, we made our way to Florence’s train station for the next leg of our journey. With a private assistant and luggage porter making the transition effortless, we boarded our business-class train bound for Naples—ready to trade vineyards for volcano views.
Tuscany Takeaways:
Don’t just stay at Castel Monastero—experience it. Book the Cantina dinner and the spa. Trust us.
A magnesium pool sounds weird. It is. And it's amazing.
Say yes to wine tastings, but even more importantly—say yes to the unplanned detours. Siena was never on our itinerary, but it’s forever in our memory now.
Tuscany was a chapter of balance: rich and restful, curated and carefree. It reminded us that the best travel moments often come from the mix—the Michelin stars and the surprise stops, the quiet mornings and the full-bodied reds.