Some years ago, my neighbour asked me if I wanted to join nine other people and rent a villa in Tuscany. Why not? It was smack in between Florence and Siena, so I signed up. But just before leaving, I had my doubts. Sharing a villa and meals and car rides with people I hardly knew — what was I thinking?

 It turned out to be one of the best trips I’ve ever had. By day one I concluded that savvy travelers rent villas. Why hole up in a hotel room when you can live la dolce vita in splendid privacy, complete with pool, and — if you prefer — fully staffed?

 So I had no qualms about tagging along with strangers for a second trip. Last month I joined three travel writers, a wedding photographer and three people in the food industry, all of us with common interests: food and wine, and craving a taste of the sweet life.

 You might think that a Tuscan villa is beyond your means, but do the math. Dividing the nightly rental by eight or so ends up costing less than an average hotel room. You may have heard about villas from hell, where the electricity and plumbing are dicey, where you have to spend the first day scrubbing countertops and walking miles to the nearest grocery store.  Not so at Montestigliano and Villa Pipistrelli.donati-villa-w

 The Montestigliano estate is nothing short of a Tuscan dream. This little “borgo” or hamlet that was originally a quasi-self-contained village and working farm sits on 2,000 acres and still produces its own olive oil. It is now a vacation retreat that comprises several villas — all former farm worker houses that have been carefully restored — including Villa Pipistrelli. Original features, such as exposed beam ceilings, whitewashed walls and terracotta tiled floors, have been carefully retained, and eclectic furnishings added.pipistrelli-pool.w

 Villa Pipistrelli, where we stayed, is about a 20-minute walk from the other villas on the estate. Surrounded by woodlands and olive trees, it overlooks the Montagnola Senese hills. Once a 17th century farmstead, Pipistrelli is so comfy and luxurious it’s hard to leave. It helps that a few members of the Donati family (owners of the estate), live on the premises — it’s like having resident concierges. Luisa Donati arranged transportation toSienaand other renowned towns nearby such as Montalcino. She even acted as translator and whisked us to local restaurants and wineries. 

 One member of our group, Nancy Krabill, fromDallas, knows her way around and speaks some Italian. She stayed at the villa in 2006 with some friends and has been back several times since.

  ”The first time I saw Montestigliano after driving up the long and winding road was like being transported to a different world — the stillness, the colours fading on the buildings,” she says. “There are a bazillion places to rent inTuscanybut I always come back here; it feels like coming home to someplace new.”road-sunshine.w

 And we saved on meals. Pipistrelli’s fully stocked kitchen included fresh bread and pastries, fruit and home-made preserves for leisurely breakfasts (espresso maker, juicer, sharp knives — a foodie’s dream), as well as olive oil made from the estate’s olive trees.

 We opted for maid service and a cook. I’m no princess, but what is a vacation if you have to make beds and do the dishes? (If you arrange ahead of time–for a nominal fee– the kitchen can be stocked, and a driver/translator booked.)

 Krabill suggested we stock up on other essentials: pasta, tomato sauce and zucchini flowers at the tiny hamlet of Stigliano. And we had a cooking lesson: we donned aprons and made ravioli from scratch then upstairs at the restaurant we sat down to eat our spinach and ricotta ravioli, the freshest greens, local cheeses and charcuterie from Cinta Senese pigs.

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 We visited the farm where these prestigious pigs, which were almost extinct in the 1980s, are now raised for cross-breeding. It is open to the public, but bring a translator. Lucky us, some pigs that don’t make the DNAgrade—unsuitable for breeding–go to “transformation” (AKA the butcher). “Eat with your eyes, smell, then taste,” advised Daniele Buffaraldi, who has raised the pigs since 1980. “Sniff the proscuitto to get a perfume of long ago.” Mere words can’t describe the flavour — ethereal comes to mind. We also sampled melt-in-your-mouth lardo and salamis — the latter stuffed into my check-in suitcase.Copy-of-sinese.pig.w

One evening Luisa Donati accompanied us to La Serva Ubriaca (The Drunken Servant) in the ancient hamlet of Torri that tourists would likely never find on their own, but it’s well worth hiring a driver/translator to get there.  Another serata (special evening) we dined al fresco at the villa, complete with accordion player. The resident chef made pizza — the crust thin as the gingham tablecloth with toppings of local ingredients — in Pipistrelli’s outdoor wood-burning oven. He even made Nutella pizza for dessert.

 Of course we toured Siena, visited the zebra-striped cathedral and climbed the huge bell tower. (When the tower was first built it was known as the Torre di Mangia, or “Towerof Eating,” because building costs were so high it was referred to as mangia guadagni, “eating the profits”.) You must have a Campari and soda or Orange Spritz at Liberamente Osteria in the Piazza del Campo. And a great gift to take home is panne forte — a wondrous dense fruitcake best eaten with Vinsanto (a special sweet wine) — from the bakery of Lorenzo “Il Magnifico,” just a few steps from the piazza.sienna-tower-.w

 You can easily spend a day in the nearby town of Montalcino, and at least a few hours sampling wines and getting a crash course in Brunello at one of many enotecas or wine shops. We chose Enoteca di Piazza, which advertises tastings from 100 wineries.  But nothing is free anymore.enoteca.sign

 This is what you do: purchase a wine tasting card for about 20 or 30 euros, choose the wine you wish to taste and insert the card under the dispensing machine. Push the button corresponding to the chosen wine and it is then poured into your glass. Of course you can also buy wines by the bottle to take home. If you purchase 12 or more bottles, they will ship to your door — free of charge — and delete the cost of the tasting. Well, some things are free, kind of.

 Le Marche: The New Tuscany

  I could easily spend a few weeks lolling about Pipistrelli, but there were places to see and cuisine to discover further afield. After a three-hour drive over the Appenines, we arrived at the medieval town ofMercatelloin theMarcheregion — firmly off the tourist grid and, Luisa Donati tells us, likeTuscanywas 40 years ago.

 Krabill has also been here before and guaranteed delicious meals, all sourced from ingredients such as wild mushrooms and truffles found within a one-kilometer radius. After checking into the fabulous Palazzo Donati (the family home) and touring the palatial grounds, we met downstairs for a supposedly “light” lunch of tagliatelle (resident cook Lina demonstrated how to make the pasta when we first arrived) blanketed in a tomato-meat sauce so flavouful I had a second bowl washed down with plenty of local red wine. We had definitely come to the right culinary locale.truffle-shave.w

 So too had Jamie Oliver. For several years in a row, Lina has won the traditional pasta competition that takes place in the main square every July. Last year the town hosted the famous chef and entourage during the filming of Jamie’s Great Italian Escape for Food Network. “But Jamie Oliver got into a fight with one of the grandmothers,” says Krabill, laughing. “He wanted to make a red sauce but the ladies said it was the wrong sauce for that region.” Don’t mess with tradition.

 We heaved ourselves back into the van and drove to Urbino, the capital of LeMarcheregion. Surprisingly, the streets of this Renaissance hill town were full of twenty-somethings. “So many young people, such as chefs, are moving back from the big cities and seeing the value of tradition and community,” Krabrill explained. Again, lucky us.

 After touring theUrbinoPalaceand detouring for retail therapy at Ceramica d’Arte Antica in Urbania — a ceramics workshop that also sells exquisite pieces — wouldn’t you know it was time for dinner.

 Not even Jamie Oliver could have cooked better than Anna Faggi at Mulino della Ricavata. Her restaurant and B&B is a converted flour mill surrounded by an organic vegetable and flower garden. We hunkered down to a dizzying amount of courses, each one groaning with local ingredients, including ravioli with borage and edible flowers from Anna’s garden. And each course was paired with local wines served in water glasses, filled to the brim.

 As if that wasn’t enough, lunch the next day at the osteria Locanda back in Mercatello topped everything — they specialize in truffles. Our plates of home-made pasta with truffles almost caused delirium and eyes rolled heavenward. Uto, the owner, proudly passed around a basket of wild mushrooms and a few truffles he’d recently foraged.

 Omigod, why wasn’t I born Italian?

 If you go

 Villa Pipistrelli, with private pool, is just one property on the Montestigliano estate. Smaller villas (from two bedrooms) share another swimming pool and are also available to rent year-round.

www.villapipistrelli.com Email info@montestigliano.it 

 Palazzo Donati in Mercatello can accommodate up to 17 people and the minimum stay is three nights.

www.palazzodonati.com  Email Luisa Donati at  info@palazzodonati.com

  How to Get There

 Fly Air Canada to Rome Fiumicino airport, then take a short train ride to central Rome. Go to the information booth at the train station—they will assist you with a train ticket to Siena. You can arrange transportation from Siena to Montestigliano when you book the villa.