The phrase “spring break” only began to cause me anxiety once we had children. In the rarefied parish of Manhattan where we live, certain parents treat family holidays as a competitive sport and they are determined to win the FA Cup. It was from one of these Premier League moms that I first heard the phrase “surf ’n’ turf”. The reference wasn’t to steak and lobster, but a school holiday where the first week was spent by the seaside in Nicaragua (“Costa Rica is just overrun with tourists now”) and the second week was spent skiing in Aspen, Colorado. Just the thought of packing for this double-shot holiday exhausts me, but then again, I’m the sort of middling salaryman who still packs his own suitcase and flies commercial. Holidays are meant to be restorative, so I’ve developed a few simple guidelines that ensure the Swiss Family Brodie returns from its late-winter shipwreck ready for a new term. It is my hope that these tips might prove helpful to those who are just beginning to travel with children.

Trip or holiday? This is the first thing we discuss before planning a break. Simply put, a holiday involves sunscreen and reading Mr John Le Carré poolside. A trip implies going to a foreign country or city for a week that will be filled with cultural outings, new foods and shopping, a favourite pastime of our 10-year-old daughter, who is fond of wearing her knock-off Balenciaga Speed sneakers to gym class despite my entreaties that she will break her ankle. Italy – and in particular Florence – is a great place for a first trip abroad. All children love Italian food and all parents enjoy chianti. The city is walkable and even a treasure trove of Renaissance art such as the Uffizi is manageable if you assign your children a simple task: “Tell me how the paintings change as we start in the 13th-century rooms and progress to the 15th-century ones.”

We like Hotel Lungarno. It overlooks the Arno River, has chic furnishings and is centrally located, so if the art historians in the family want to slip out to spend an hour looking at the Masaccio frescoes at Santa Maria Novella, the shoppers can peel off to sample fragrances at the Santa Maria Novella apothecary (the aforementioned 10-year-old’s favourite place).

When deciding between a trip or a holiday, it is important to know your customers and pay attention to the season. In my experience, summer is a better time for a trip. After a long winter term, going on holiday somewhere hot elevates everyone’s mood and helps shake off whatever virus we’ve been passing around the house for weeks. For parents of younger children, there’s also a sense of release that comes in the form of temporary relief from having to bundle up your kids in layers of woollens every time you step outside.

Once you know where you’re headed, one of the more important decisions to make when travelling with children is where you’re going to stay. If you’re like me, the thought of a family-friendly resort is a turn-off. The closest I want to get to Disney is a Gucci collaboration. I’ve never understood those parents who say, “We go to Atlantis and the kids love it.” Spending one’s hard-earned cash on a waterpark-cum-casino in the Bahamas strikes me as ass-over-tea-kettle thinking.

Instead of altering our habits to make our children happy, we are great believers in working them into our sensibility, which involves some chic Caribbean hideaway where tennis is played in whites, the toiletries are Aesop and gentlemen still wear jackets in a mahogany-panelled dining room at night. Our children may not know how to jet-ski, but they do know how to use the doubling cube in backgammon and to warn the barman that “Dad will go ballistic if you use a lime for the twist in his martini”. One pro tip is to investigate whether the resort you’re considering has a kids’ club. We love our children, but we love them even more when they’ve spent the morning supervised by resort staff.

Hotels and villas have their charms, but when travelling as a family, cottage life is often a better option. If you’re going to be staying in a hotel, you’re probably weighing up the higher cost of booking two rooms against cramming everyone into one. We’ve come to prefer a villa within the confines of a resort. It’s usually about the same price as two rooms and there is something relaxing about having common areas where we can come together and different rooms to escape to. Also, a lot of kids’ menus at resorts are heavy on chicken fingers, pizza and pasta, so having your own kitchen and being able to ensure your kids consume the occasional vegetable means they won’t return to school with their pelts all shiny.

For my wife, one of the downsides of being married to a misanthropic solitaire is that we take only one holiday a year with another family. The upside of travelling with other families is that the children can entertain one another. The downside is you have a front-row seat on another couple’s interpretation of Who’s Afraid Of Virginia Woolf? Invariably, there will be a night where someone has one too many Rummy Dum-Dums during happy hour and then goes off on their spouse. For whatever reason, this seems to happen more on holiday than at home.

Don’t get me wrong. I like being at a resort where we run into people we know and get together for impromptu drinks and dinner. I’m just a little uncomfortable with the idea of having every meal with several other families and feeling compelled to engage in group activities. There is no transitive property that says just because our children are friends, we need to be. My preferred holiday iCal does not include lots of off-property outings. There must be huge blocks of time to tan myself the shade of a cortado, play some lacklustre tennis, disappear for a cinq à sept and then re-emerge from my nap in time for supper.

We’ve rented the same villa in Jamaica every spring break now for the past five years. The house is on a hillside overlooking the ocean and has a pool. It comes with a maid and a chef, and the owner seemed to have cornered the market for D Porthault linens back in the 1990s. It has become a fixture on our calendar, a week we all look forward to and a place where we hope our kids will continue to join us when they are grown up. After the savagery of the winter term (or what we adults call Q1), we all need that lazy week. We are fine with surf, but prefer to leave the turf to others.