The conversations grew increasingly animated. Seated at the long dining table on the villa’s covered terrace, surrounded by three vacationing Italian families, we attempted to keep up with the happenings. The families knew little English; we knew little Italian. Kindly, the Italians used recognizable Italian and English phrases to keep us in the loop. Laughter reigned. Topics ranged from the day’s explorations of nearby hill towns to the finer points of Italian dining. Empty carafes of the local white and red wine lined the table. Nana Giullia, our fabulous cook, had just served the final course, heaping bowls of fruit, following the antipasti, salad, pasta, pork, and dolce. After all her work, she decided it was high time to join her partying clients. She received a huge cheer as she exited the kitchen with a tray of glasses and a bottle of grappa for the final toast of the evening. Saluto! Ciao! A toast to the joys and tastes of Tuscany!

The fantastic family meals were just one of the many highlights of our stay at Il Grande Prato, a beautiful, perfectly situated villa in the Tuscan hills near San Gimignano. The villa occupies three acres within the large working farm complex of Castello di Oliveto. The owners, Vito and Giullia, purchased the run down farm buildings and surrounding land seven years ago and have recently completed their "labor of love" restoration, outfitting their villa for vacationing guests. The large centuries-old farmhouse has been tastefully redone as a home/office/albergo with seven guest rooms. My wife and I had rented one of the two apartments in an adjoining retrofitted farm building. A private patio served as the perfect place to enjoy our own meals or snacks. It was but a short walk to the pool and to the country road that followed the ridgeline past vineyards, fields of sunflowers, cypress trees, and herds of goats and sheep. The villa displayed tasteful country touches, including plentiful flower boxes, sculptures, patios, a horse paddock, and the family’s friendly dogs and cats.

The villa is one of hundreds that offer guestrooms or apartments in the Tuscan countryside, ranging between Florence to the north and Siena to the south. Florence, Pisa, and Siena are only an hour’s drive from Il Grande Prato. The smaller, medieval hill towns of Certaldo, San Gimignano, and Volterra are even closer. The famous wine region of Chianti is 90 minutes away along isolated gravel roads passing small farms and vineyards. Since we had visited Florence and Pisa on previous visits, we decided to alternate days enjoying the villa’s pool and countryside with days exploring Siena, Chianti, and the smaller hill towns.

We enjoyed getting lost in the maze of streets that branched into the surrounding neighborhoods. Siena exhibits its pride and energy each and every day of the year. The residents take their neighborhood allegiances seriously, following a 700-year-old tradition of competition. The annual Il Pailo games are culminated by a daring horse race that ends in Il Campo piazza. We encountered numerous flag-bearing groups touting their neighborhood for the upcoming events. Children were everywhere in the streets, playing and shouting merrily. We were thrilled to view a traditional Italian wedding promenade as a crowd cheered for the groom and bride, trailed by her 20-foot veil. After a day of exploring and feeling Siena’s pulse, we enjoyed the perfect cap to the day with dinner in a relaxing trattoria.

Smaller and quainter than Siena, San Gimignano sits high on a hilltop, beckoning to visitors with its array of towers. Fourteen towers of an original 72 still stand, giving San Gimignano the reputation for being one of Tuscany’s best-preserved medieval towns. The towers were constructed in the 1200s by feuding noble families for purposes of warfare and in competition for the most imposing structures.

We entered the walled city by Porta San Giovanni and enjoyed the line of centuries-old buildings and shops along the main thoroughfare leading to Piazza della Cisterna, aptly named for its 13th century well. Walking under a large arch at the far corner of the square, we came upon Piazza Duomo, with the town’s most impressive towers, including Podesta’s Palace Towers and the Clock Tower, measuring 51 meters. The Duomo (Collegiata) here was worth our visit, as it contains a unique set of original frescoes dating from the 12th and 13th century. Uphill from the Duomo, we explored fortress Rocca di Montestaffoli with incredible views of the town below and the surrounding countryside. After completing explorations along Via San Matteo and Via Romite, we looped back to Piazza della Cisterna for lunch at one of the outdoor cafes. Later that afternoon we sampled wine at several shops, then chose an excellent bottle of Chianti.

As our week in Tuscany continued, we grew intoxicated with the relaxed pace: the golden, sunny days, the historic hill towns, and the tasty and friendly dinners served on Il Grande Prato’s terrace in the warm evenings. We knew that we had discovered the perfect combination for appreciating Italy’s most celebrated region. Even if we couldn’t buy our own Tuscany home as featured in the recent bestseller, Under the Tuscan Sun, we knew we would again visit Il Grande Prato and other guest villas under the Tuscan sun.