Italian Villas For Your Euro Road Trip | My Family Travels

Our kids wanted to go to Venice – my wife and I wanted to go to Tuscany. Here's how we hit the autostrada and did both.

On a recent spring break in Italy, after wandering by boat and foot through the Venetian fairyland, we rented a really nice four-door Alfa Romeo at the Venice garage and shifted gears. The transition from Venice to Tuscany is arresting. Automobiles substitute for boats, castles stand in for palaces, and meat replaces fish. Our kids really enjoyed the change of scenery on this EuroTrip, a road trip actually — especially when we pulled up to our “hotel.”

Torredepecci, a Villa of Distinction

Too small for the Michelin map, the tiny hamlet of Stigliano rests in the green hills a dozen kilometers southeast of Siena, consisting of little more than a cute restaurant on a tiny square, some picturesque stone houses and a couple of inns. Ours was a small property called Torredepecci, offered by the rental company Villas of Distinction: four units housed in a solid rock tower, a prized example of 13th century Siennese fortifications against Florence.

Despite its origins in war making, today Torredepecci is bathed in peace. We occupied the top two floors: a spacious bath and comfy double bedroom, a large living area and kitchen and a stunning top floor bedroom in the former battlement surrounded by Tuscan light and spectacular views. The spiral staircase leading to the sunbathed top floor totally unsettled my wife (and makes this unit of the castle questionable for tiny kids), so we offered the king size bed and accompanying vista to Maddy and Jamie and slept a la Ricky and Lucy in the double beds.

The modern amenities contrast quietly with the thick stonewalls, wooden ceiling beams and Tuscan views. The kitchen is equipped for cooking full meals (including a microwave), although it may present a bit of a challenge for those accustomed to Viking ranges and granite countertops. A convenient washer and dryer in the basement of the tower came in really handy (I presume it was the owner who graciously hung our damp laundry on the clothes lines overlooking the town square).

We loved shopping at the supermarket in nearby San Rocco a Pilli for our simple breakfasts of coffee, juice, country sausages, bread and cheese. We even hunkered down in our tower with supermarket pizza one quiet evening — frozen pizza in Italy!? San Rocco also has a few cute restaurants, a pasticceria for pastries and gelato and no other tourists.

Road Trips Under The Tuscan Sun

Torredepecci features a small pool and paths for wandering the wooded countryside, but we used it primarily as base camp for day trips to a half dozen medieval cities littered throughout southern Tuscany: Montalcino, Montepulciano, Pienza, San Gimignano, Sienna and Volterra, most under an hour drive along winding country roads through classic Tuscan landscapes. In no particular order:

Volterra is stunning. Our host at Torredepecci highly recommended this town, a 90-minute drive northwest, perched above a cliff and enclosed by Etruscan and medieval walls towering over neighboring valleys. We arrived late morning, had a satisfying lunch at Ristorante Etruria in the main square and then wandered around the city. Despite its small size, the town is replete with ruins of a Roman amphitheatre (dating back to 10 B.C.), 13th-century palazzos, narrow winding streets and a lovely park in the shadows of a castle. Beautiful! Take your time following the winding route SP541 north over rolling hills until it meets SR68, and heads west to this village.

San Gimignano, despite the crowded streets and overabundance of shops, is well worth a stop. The town square is lovely, the medieval towers made us gape like tourists in Manhattan, and the window-shopping is delightful. Similar to other Tuscan towns, the narrow side roads off the beaten path, especially those overlooking the post card perfect views, are more memorable than the typically teeming main streets.

Montepulciano, a small town known for its sturdy wine, is a nice diversion on a beautiful promontory and a good example of the Renaissance period. The Piazza Grand is charming, and its Palazzo Communale has a tower for viewing the Tuscan countryside (I can never get enough views – the kids enjoyed the climb and the feeling of being on a precarious precipice.) The nearby Chiesa della Madonna di San Biagio, set just below the walls of Montepulciano and reached through a double row of towering Italian cypress, is a lovely lesson in architecture, incorporating Greek, Renaissance and ecclesiastical influences.

Pienza is a gem, a jewel of a town that can be admired quickly or fawned over at length. A planned Renaissance city commissioned by Pope Pius II in the 15th century, Pienza is set on the edge of a quintessential Tuscan mount with striking views of the Orcia Valley. Numerous films have been shot in and around the town, including “Gladiator” and “The English Patient,” taking advantage of the city’s mystique and the Orcia Valley’s otherworldliness. Despite Pienza’s large number of visitors, there are few more tranquil spots than the town walls behind the cathedral, perched above the Valley on streets named “love” and “kiss.” A truly lovely and romantic town.

Montalcino is known primarily for delicious and super expensive wines, and it was the least fascinating for our kids. This village’s main interest is the well-preserved pentagon fortress with parapets overlooking the Tuscan countryside. We enjoyed the fortress’ cozy ground floor enoteca serving Brunello de Montalcino and other local wines.

Our Favorite Tuscan Town: Siena

For us and the kids, Siena was the favorite Tuscan town. It’s the perfect size for kids and not frenetic like Florence. Come once, come 10 times, there is always another treasure around the next corner.

Jamie insisted we climb the Torre del Mangia on the Piazzo del Campo; 388 steps later, after shimmying past other brave hearts, we relaxed atop the crenulated tower. Tuscany is no more beautiful than from this perch. Maddy and mom grabbed some fries from the Italian fast food chain Spizzico and relaxed in the Campo below (it always amazes me that the Palio horse race fits into this square).

Our kids loved the Museo della Tortura, and so did we. Not at all like the Ripley’s Believe-It-Or-Not trap we envisioned, the Torture Museum depicts all sorts of horrors done to women, cripples, strangers and just unlucky folks throughout the Dark Ages: stretching racks, iron maidens, psychosis inducing contraptions, devices that split people in two, orifice widening tools. The descriptions were vivid and appalling — perfect for an 11- and 13-year-old. Our kids pooh-poohed this wanton behavior as a freak of history until we reminded them that some of this depravity is quite contemporary. Oh, yes — great photo ops.

In a similar gross vein, our kids actually enjoyed the enormous Basilica di San Domenico that dates to the 13th century – perhaps not the church itself but the preserved head of St. Catherine that sits in a glass case, complete with the infamous chipped tooth from her fall on the steps of the Baptistery. They also surprisingly enjoyed St. Catherine’s home down the street that was turned into a sanctuary in the 15th century, complete with stories of stigmata, self-beatings with a switch, and celestial visions.

Sienna seems to drip money, particularly along the Via Banchi di Sopra with its ornate, crusty old buildings and palaces, upscale shops and the always-bustling café Nannini, a Siena institution with its weighty crystal chandeliers and worn marble floors. Just another lovely stop for gelato for the kids …

Details, Details

Our Tuscan tower was ideally located. Each of these jaunts ended the same way: another stracciatella gelato and a short drive back to our tower. We were delighted that Torredepecci survived the region’s battles to serve its serene new purpose.

Torredepecci was rented through Villas of Distinction. Weekly rates in 2009 for the two-bedroom, one-bath top unit: US$1208 per week midseason and US$1766 in summer. Additional units in the castle can be rented – or the entire tower can be rented in the low season (March) for US$3575, midseason (May) for US$4299 or high season (summer) for US$5236. There is a seven-night stay minimum.

Getting around Tuscany is part of the pleasure and a rental car is essential. There are numerous options located in the large garage near the shuttle bus stops in the ugly Piazzale Roma. We rented from EuropeCar, a tiny office on the main road in and out of the Piazzale. After a lengthy check-in, the attendant brought our car to the curb and off we went. Drop off was easy and convenient to all transportation.

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This story was accurate when it was published. Please be sure to confirm all rates and details directly with the companies in question, and stay up to date with current events to ensure a safe and successful trip.