I had the great fortune of being on a trip organized by Trafalgar Tours, specifically, its Be My Guest program, which opens usually closed doors and permits travelers to utterly savor the tastes and notions of a region. On my trip, I visited gorgeous Tuscany in Italy.

Normally, I avoid group tours, but I was so busy laughing and learning on this trip that none of the usual tour group dynamics—monotone guide voices, instantly forgotten facts, half-stabs at visiting anywhere, etc.—were able to seep in. And joy of joys, there always seemed to be red wine to sip and fried zucchini flowers to munch on.

The accommodations were perfect, too. The road, Via Empolese in Cerbaia, winds alongside the sublime Villa il Poggiale near the small village of San Casciano Val di Pesa and always seems to be busy, a small mystery to me. 

A step away from the villa, a side road leads to a world of olive fields, vineyards, sun-kissed Tuscan farmhouses, narrowing lanes and grassy driveways marshaled by small birds called Black Redstarts. In November, the smell of olives perfume the air, and half-hidden men armed with long poles and large blankets move along groves and strip fruit from the trees.

The next day I visited the Fattoria di Maiano to see where some of these olives end up. Running this fattoria, or farm, on the other side of Florence just south of Fiesole, is the Miari Fulcis family, made up of generations of counts and countesses. The current head of the farm is Contessa Lucrezia Miari Fulcis dei Principi Corsini.

Fattoria di Maiano is the largest farm in the area and produces the delicious Laudemio olive oil (other oil manufacturers also market their wares with this name, as a collective). Their house—well, mansion—possesses a columned courtyard, a terrace overlooking maze-like topiary, a church, Spinello Aretino’s fresco La Madonna della Misericordia and an olive press called a frantoio in Italian.

A tap gushed oil, and our group was welcome to dip our fingers in the flow. Go ahead, be our guest, as Trafalgar frequently encouraged us. Parts of the movie adaptation of E.M. Forster’s novel A Room with a View were filmed in the main dining room.

Back at the ochre-yellow Villa il Poggiale, I marveled at never finding my way from my room—Room 1—to anywhere I wanted to go. It was fantastic to get slightly lost and discover new sitting rooms, the kitchen, the back door, the side terrace. The building too has a sense of mystery about it — something the Scottish hotel administrator from Selkirk added to.

The road to Florence passes by the village of Pozzolatico and the basilica of San Miniato al Monte (St. Minias on the Mountain). It provides one of the best views of Florence’s Duomo and Campanile.

The church has some ornate interior decoration, ranging from small details of knights wearing conically shaped helmets while attacking dragons to large frescos completed by Aretino. The exterior stairs leading to the basilica also are dramatic and reminded me slightly (although these stairs lead straight up) of those at Bom Jesus do Monte in Braga, Portugal—probably because both are white from whitewash and the Carrera marble.

Back to Pozzolatico, we took the vegetables we had purchased in Florence’s San’Ambroglio market and started to prepare lunch at the expansive I Tre Pini restaurant, owned by the marvelous Libero Saraceni (“Free Saracen”). I was in charge of the tomato Tapenade soup, and I also helped make ravioli. I now felt less like a guest and part—albeit a small part—of Tuscany’s fabric of life.

Stomach filled, I investigated Florence. The exterior of the Duomo is quite beautiful, as are the Gates of Paradise on the Battistero di San Giovanni where Dante was baptized. It is a short walk to the Ponte Vecchio, but I’d preferred to look at that bridge from the adjacent Ponte Santa Trìnita, which was destroyed by the Nazis in August 1944, and see the Vecchio’s colors and shapes reflected in the River Arno rather than the reflections in the tacky gold on display in the tacky gold shops.

In addition to painting, Giorgio Vasari built the Vasari Corridor, which connects the Ponte Vecchio with the Uffizi Palace in Florence—just another of the connections that make history and modern life here fascinating and palpable.