'Miracolo!' 'Spettacolo!' 'Bellissimo!' 'Complimenti!'

It was true what we'd been told about Italians loving children. Only 20 minutes off the plane and here we were at a hot-dog stall by the Leaning Tower of Pisa, with the owners praising Eddie's cheeks as the very height of rosy chubbiness.

We were more than chuffed. After weeks of agonising over what to do for a holiday before my wife, Jane, went back to work, where to go, what to take and whether to go away at all if it was this much trouble, the Italians' enthusiasm seemed like an instant pat on the back for our final choice.

It comes to all new parents, and many of our family and friends had gone through it before us, but though their combined advice was helpful, I guess you just have to work out for yourself how to take a baby on holiday when you're used to taking off as a pair. We've had some great trips, too - from our first adventure in Cuba (when there wasn't even a Lonely Planet guide!) to exploring Rajasthan by train, not forgetting tours round Spain, France and Germany by motorbike (the Harley's for sale, by the way, one careful owner; Jane wouldn't go for the sidecar option).

The main complication, it seems, is that your little one is rapidly changing, so what might suit one month won't work the next. As a dry run, when he was three months old, we took Eddie on the Eurostar to visit friends in Brussels, and that was easy as confidence-boosting pie. Bus to Waterloo, on to the train, only three hours to entertain the baby who was fascinated by the world whizzing past the window anyway, then met by our friends to chauffeur us to their home. We didn't need feeding bottles as he was being breast-fed, his few clothes fitted in our bag and he would happily sleep in his buggy or car seat if we went out to a restaurant in the evening.

For the big fortnight's holiday, though, he was going to be five months, eating three solid meals a day and with a regular bedtime. He'd need toys; as many changes of clothes as ourselves; beakers, bowls and bibs - enough for his own suitcase on top of ours. We wondered about resort hotels, but in several cases crèches only took children over six months; others had baby-listening facilities, but we've found that the three of us sharing a room means a poor night's sleep for everyone. And we were mindful of the experience of some friends who, having once paid for an expensive resort with toddlers' club, never put their kids in because they so relished the chance to have time away from work with them. Not only that, but because we've been cooking Eddie's food rather than just buying ready-made pots, we'd need somewhere to prepare it. Self-catering it would have to be.

Next decision was where. We nearly went for a 'big one'; long-haul flight to America, then touring the Grand Canyon and beyond by motorhome. But that would not have been cheap, and with child-care bills about to start raining down, we wouldn't have our former childless people's luxury of paying the holiday off over subsequent months. Europe beckoned.

We discounted France straightaway on the ground that we'd no doubt be going there lots of times in the coming years; we'd been to Andalucia the year before and found the people unfriendly, so were put off Spain; we thought about Turkey but didn't trust our ability to negotiate hospitals if Eddie fell ill. Greek island-hopping had been high on our list of future 'must-dos' before Jane fell pregnant, but the thought of lugging bags on and off ferries three or four times over, plus buggy and baby on top, sounded too exhausting. Not only that but when we looked at brochures, many Greek villas only had a 'kitchen corner' - ie, a Baby Belling sitting on a fridge - as opposed to a full kitchen in which to prepare meals. And Eddie was too small to enjoy a hot beach holiday anyway.

So we plumped for a country we've enjoyed many times before, where we could expect a friendly welcome, where the eating out would be good, the shops were full of lovely produce to cook Eddie's and our own food, where there were beautiful places to explore during the day, and where we felt confident of quality health care just in case - Italy.

That's how we came to be chinwagging with the hot-dog sellers in Pisa. We'd picked up our hire car and popped into town to stretch our legs after the flight, before embarking on the drive to Tuscany and the villa we'd rented. There'd been a slight hiccup when the infant car seat we'd ordered turned out to be a type that, in the UK, only bigger children would be allowed to use. We started cursing ourselves for not having brought our own, even though it would have been more bulk to carry, but relaxed when we realised the seat could be attached rear-facing, even though the hire manager didn't know it.

The villa was between Siena and Monteriggioni, and its owner was there to greet us when we arrived. It looked fantastic, with a comfortable sitting-room, nice bedrooms, cot for Eddie, and a kitchen with hob, oven-grill, fridge-freezer, dishwasher and washing machine, pool, barbecue and even a thoughtfully placed herb garden for the cook. There was a welcome basket of goodies too - pasta, passata, oil, tea, coffee, biscuits, and a bottle of local Chianti - with a note from the rep giving a time she'd be round next day to answer any questions we had about places to see.

Things quickly settled into a routine: wake about 8am, a hearty breakfast of fruit, a kick around with toys, nap about 10.30, a drink of milk, a lie-down, light lunch, an hour or two being led to some sight of interest, a couple more drinks, a nap, a bit of 'matwork' exercise, dinner, sing-song, bath, massage, a last bit of milk, then bed about 7pm. And once I'd settled into that, Eddie sort of fell in with it too... (Oh, how he'll love his dad's holiday jokes when he's older.)

In other words, holiday life was pretty much the same as at home, except there were fewer chores and our daily trips out were to see stunning medieval hilltop towns such as San Gimignano and renaissance masterpieces rather than Sainsbury's in Dalston. Not that supermarkets were out of bounds. Our first expedition was to find the Co-op in Siena and stock up, which we managed without too much grief and with enough time to spare to nip into the city centre for an ice cream in the thronged, sunny Campo square. Which led us first to utter the phrase that ended up as our holiday motto: 'This is the life.' After our days out we'd settle the baby for the night, then relax with a meal, some wine, play cards and talk about Eddie's latest developmental triumph.

For starters, we'd not counted on how continental shutters would make him sleep longer, which gave Jane her first night's uninterrupted kip since he was born. When it was warm enough, we could lay a blanket out on the lawn, whip his nappy off and let him twist and wriggle to his heart's content, which led to him sitting up unaided for the first time and discovering that he could indeed put his foot in his mouth if he pushed hard enough. Just like his dad.

For our second week, we moved to a different, even more sumptuous villa about 20 minutes out of Florence, but our routine was much the same, boosted by some really hot weather, so we got a couple of days sunbathing by the pool while Eddie amused himself in the shade of a beach umbrella. And this villa had a highchair which we tried him in for the first time, which led to his first-ever meal without plastering himself in goo.

All in all, having the baby with us hardly clipped our wings at all. We didn't manage more than one evening meal out: it was too stressful, after he didn't go to sleep on the way to the restaurant and we spent most of the time between courses trying in turn to rock him off in his buggy. Instead, we had longer lunches on outdoor tables, so if he got bored we could walk him up and down.

Nor could we climb church towers to admire the view or queue for hours to get into the Uffizi in Florence; luckily we'd done all that on a previous visit so we didn't feel we'd missed out. And we had to restrict our wanderings to a maximum 40 minutes' drive away or he got fed up or hungry; we ventured to Montepulciano one day and strayed over into dinner time, so Jane had to climb into the back seat and feed him on the move.

Those things didn't matter. It was the most relaxing break we'd had for years, one that I know will become golden in memory.

Nothing could beat the sight of my new family, Eddie sitting on his mum's lap, on a sun lounger while she read aloud the padded masterpiece My Pig Book. Unless you count the coachload of Italian pensioners in a Chianti hilltown who descended on us in a mass huddle to coo over Eddie, click their fingers in a peculiarly Italian way and call: 'Ciao!' 'Bellissimo!' 'Complimenti!'

A helping hand for parents

Esprit Alpine Sun (01252 618 300)
Catered chalet holidays in the Alps with nurseries staffed by British nannies and activity clubs for children aged four months to 12 years.

First Choice Villa (0870 750 0001)
Some villas have a First Choice Kids Club within easy driving distance: £40 for six days' membership. Baby packs cost £45 for one week and include cot, highchair, buggy, steriliser, bottle warmer, buoyancy jacket, protective sun tent and car sunshade.

Greek Islands Club (020 8232 9780)
Babysitting service available with English reps. A children's hamper (with soft drinks, chocolate, an inflatable Lilo, a fishing pack and a quiz book), cots and highchairs provided on request.

International Chapters (020 7722 0722)
Babysitting, tennis classes, swimming lessons and other activities available in St Tropez properties. Cots, highchairs, pushchairs, baby baths and play pens can be booked.

Meon Villas (01730 268411)
Pre-bookable Baby Packs with steam sterilisers and bottle warmers in selected destinations for £20 a week, plus highchairs for hire. Will recommend childcare agencies who can supply registered 'holiday nannies'.

Scott Dunn Mediterranean (020 8682 5040)
Villa holiday price includes maid, cook and a nanny (up to three nannies in larger properties) for five and a half days a week. Babysitting available two evenings a week. Cots, highchairs, buggies and sterilisers can be booked ahead.

Simply Travel (020 8541 2200)
Complexes in Corsica, Crete, Turkey and Zakynthos offer qualified nannies, creches for children aged six months to five years, and kid's clubs for five to 10 year olds. You can book whole days or half-days. In Portugal, a 'flying nanny' service is available in the summer months.

Sovereign (08705 768 373)
At a cost of £35 for one week, Sovereign will provide a Baby Care package which includes cot, high chair, buggy, sterilisers and bottle warmers. Games boxes for older children are £10.

Factfile

Paul Simon and family travelled to Tuscany with Simply Travel (020 8541 2200), which offers villa holidays and city breaks in Italy, Portugal, Spain, Greece, Turkey, Madeira and several Mediterranean islands.

The following villa holiday prices include flights from a choice of UK airports and car hire. Children's discounts are available in some months. Infants under two are charged a flat fee of £50, and must share a parent's seat on the plane. Cots, child's bedding and highchairs are available. Casa dei Castelli, near Monteriggioni, has three bedrooms and costs from £650 for a week based on three sharing, then £400 for a second week in low season, (up to £995 + £600 in high season. (If six share the price falls to £450 + £215 low season, £710 + £330 peak.) Three-bedroom Casa Rossa, near Montespertoli, is £620 + £275 low season, £935 + £575 peak for three sharing. (For six:£430 + £165 low, £690 + £310 peak.)