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Tuscan holiday, family style: The ticket to effortless travel may be leaving all the planning to the experts –

The bag of eggs I bought today — yes, a bag — came with a picture of the chicken that laid them, and a poem.

I am very pretty Gina

In the henhouse I am queen

I am envied by cockerels and hens

for my coloured feathers

I make healthy and genuine eggs

to make zabaglione and cremine

This is not a Portlandia sketch, but rather the way they do things at the ortofrutta (greengrocer) in Colle di Val d’Elsa. South of Florence and a half-hour drive from Siena, the ancient Tuscan town is renowned the world over for its crystal glassware, its cathedral with its neoclassical façade, and its grand medieval palazzos, but for me it will always be remembered for its eggs.

I might never have known about the grocer, accessed by what looks like a residential driveway, if I didn’t have a concierge team helping to plan my vacation for me before I arrived. Granted, most people who travel as part of the Exclusive Resorts private members travel club, as I am for this trip, probably don’t share my interest in no-frills grocery shopping.

Exclusive Resorts is not exactly a budget travel experience. Joining the club starts at $175,000 (U.S.) for a 10-year membership, and that’s not accounting for the cost of accommodations (members are expected to travel 15 to 30 nights annually). This grants access to a portfolio of 400 vacation homes across 75 destinations, plus a team ready to help make a trip effortless, from a personal concierge to an on-call chef and full housekeeping.

In the 5,000-square-foot villa my family is staying in, it’s tempting to spend our entire vacation between the heated onyx pool, the vine-shaded courtyards and the incredibly comfortable bed. But I want to see more of the area, so the concierge team suggests we visit nearby Monteriggioni, a perfectly preserved, medieval walled village, complete with towers so impressive, Dante Alighieri referred to them in his Divine Comedy as “horrific giants.”

Monteriggioni was built by the Sienese as a front line in their wars against Florence during the Middle Ages. My son and daughter, at almost 3 and 7 years old, are more interested in the gelato than the village’s rich literary history, but they delight in walking along the ancient fortified walls, imagining themselves defending the town from invaders.

They also make friends with a local cat that lives beside the 13th-century Church of Santa Maria Assunta in the main square, Piazza Roma. Sadly, the “Monteriggioni in Arms” museum is closed when we visit, but they’ve kindly left a mannequin in full armour out front to scare everyone.

We say arrivederci to the local cat and race back for a private pasta-making class at our villa. The chef, Rita, is patient and encouraging to the kids, who create something approximating fresh pasta dough but find the most success in simply turning the crank of the pasta machine.

The ravioli, along with the roast lamb and sautéed rapini, is phenomenal, exactly the kind of home-cooked Italian meal of travel dreams. Almost as thrilling, though, is the fact that by the time we finish the last bites of baked fruit with ice cream, the dishes are all done and the kitchen spic and span.

The next morning, Rita is back and has laid out a breakfast spread that seems meant for a family of eight: pastries, fruit salad, a choice of juices, toast, hand-sliced prosciutto, various cheeses, eggs done to order. We do our best and then pack up the remainder for snacks during our day in Siena.

Half an hour from Casali di Casole, the 4,200-acre estate where our villa is situated, the brick tower of the 800-year-old Basilica of San Domenico comes into view. We’re here to meet Stella Soldani, a guide with ToursByLocals, a Canadian company that began in Vancouver in 2008 and now employs nearly 4,500 guides in 191 countries. Our tour is designed for families, but we know little else about it.

“Siena is divided into 17 different contrade, or districts,” she explains, while the kids struggle to pay attention. “Each one is represented by a different animal or feature.” Now she’s got their attention. Handing out printed sheets, she asks the kids if they can identify some of the symbols.

“Unicorn, owl, giraffe, panther, wolf. Dragon!” they shout, eager to get on with finding these creatures. Soon they’ve spotted a porcupine relief on the wall of an ancient storehouse, a dragon statue in a courtyard, and in the Jewish quarter a wall painting of an elephant carrying a tower on its back. “This is the torre contrada,” Stella explains, “my district.” We all agree it’s the best one.

In the district of the goose, we find the medieval Fontebranda fountain, so ancient it appears natural rather than man-made, with massive, colourful koi gliding through its crystal-clear water, its ripples reflected in a series of vaulted arches.

Nearby, children are practicing for the Corteo Storico, the costume parade that precedes the famous horse race Palio di Siena, held in the main square each July and August. Although they’re dressed in civilian clothes, and their drumming and flag waving lack synchronicity, we watch entranced, while trying to keep my son from jumping in with the koi.

Our tour ends, as all good things in Tuscany seem to, with gelato. There are dozens of options, but Stella prefers Grom above all others and I can see why. The purity and intensity of the flavours, especially the pistachio and gianduia, are matched only by the silky texture.

When we say goodbye to Stella, my son, who played shy at first, offers her a big hug, and I realize how unusually seamless this whole family trip has felt, due in no small part to someone else handling all the planning and guiding around, so we could actually vacation.

On our last day in Italy, we have a few hours in Florence before our flight, so I ask the Exclusive Resorts concierge to compile a map of the city’s highlights for a quick walking tour. Our first stop, of course, is at the Duomo, a building so grand and dramatic, it’s hard to fully comprehend.

At the Piazza della Signoria, we eat frittelle di San Giuseppe, rice fritters fried in olive oil — it’s Father’s Day in Italy and this is the traditional Tuscan snack for the occasion — by the Fountain of Neptune and watch the pigeons bother the replica of the statue of David.

My daughter, who is obsessed with Greek mythology, is drawn to another statue, however. “Dad, that’s Perseus,” she exclaims, racing off toward Benvenuto Cellini’s 500-year-old bronze sculpture of the demigod holding aloft the writhing, severed head of the Gorgon. I don’t know who’s more thrilled by the unexpected sight.

For all the luxury of this trip, it’s this serendipitous encounter, completely free and completely unexpected, that I’ll cherish forever. Well, that and a special bag of eggs.

Writer Chris Johns travelled as a guest of Exclusive Resorts and ToursByLocals, which did not review or approve this article.