Planning on getting away from it all these cold, dark months of winter? Kate Ancell has a few things to pack away for thought, while youre packing for away.

Illustrations by PVE Designs

When I was just a young thing, filled with idealism and stamina, I wondered why on earth anyone would ever choose to spend a good third of their year away, in temporary digs (even if they belong to you, second homes so often feel secondary at the beginning of every stay, with their lack of comfort foods and abundance of scratchy linens). And then, a few years ago, cameth January. And I realized—of course! This is why we flee…because winter here is miserable. Needless to say, that was also the day my “Great Retirement in La Jolla” plan was born (I’m still refining the rough edges…stay tuned, though!); and the day I resolved to make it through winter using a combination of resilience, steely determination, and a willingness to accept any and all opportunities to be elsewhere, at least occasionally, during the long dark months. But travel—which so many of us are plotting as we speak—brings with it its own set of pitfalls, which is why I thought it would be worth addressing at least a few of them here, for you now. So why not take a moment to step away from sock sorting and shoe stuffing and run over the basics with me?

On the Road Again

If you’re planning to be a guest in someone else’s home (or club—they equate to the same thing, really, although you’ll probably have to bring along less folding tip money if you’re staying in a private residence than otherwise…although not always, as I discovered once on a weekend stay at a friend’s very swanky country home, when the junior housekeeper was deputized to keep me turned out and comfortable, and succeeded in making sure I was a nervous wreck all the time), the first thing you need to remember may seem counterintuitive, taught as we all are to be polite above all. Which, of course, we should be!—but polite does not mean “wishy-washy,” and really, is there anything more tedious than a guest who doesn’t know his or her own mind, and seems not to have had an original thought of their own?

It is to be hoped that you are heading off on this marvelous vacay because the location, as well as the hosts, has something to recommend it…sea, sun, sand, or snow; so your first obligation is to do your homework. What might you like to visit? Where might you like to go? How do the locals spend their time? Once you’ve familiarized yourself with the high points of your chosen destination, think about your own interests. For example, I no longer ski. I have skied—for years I threw myself down chilly hillsides, stumped about in ill-fitting boots, shared interminable lift rides with strangers, until it occurred to me: I can quit! I don’t have to ski, and it’s not a character flaw! This, I can tell you, was a revelation…as was the discovery that, although I don’t like to ski, I do quite like skiing holidays—and I’m an asset, I tell you: Because I’m not hitting the slopes, I’m more than happy to drive SUV-loads of ski bunnies right to the front door of the resort; and I’ll pick up, too. And the après-ski? Well, it would be rude not to participate, wouldn’t it? The point here is, just because you don’t ski, or play tennis, or scuba dive, or whale watch, or whathaveyou, doesn’t mean that you can’t have a fabulous time. The key is just to be completely straightforward with your hosts ahead of time (before they’ve booked the boat, for example). Say: “You know, I absolutely don’t swim in the ocean, but I love to lie near it.” Or whatever. Above all, make sure that your hosts know that, just because you do or do not want to do such-and-so, you will not need entertaining. You will not need nannying. Nothing kills freewheeling fun like feeling like you’ve got to supervise.

Easy Does It

Of course, knowing your own mind and having some independence does not mean becoming a vacation bully—I won’t do this, I’ll only do that…indeed, staying with others means, first and foremost, being willing to go with the flow. The ideal situation, by all counts, would entail staying with friends who have an equivalent like of togetherness, or—conversely—aloneness. Like college school girls who only travel in packs from the bar to the bathroom, guests and hosts who can’t bear to be alone or make decisions on their own can quickly wear on the nerves like nails on a chalkboard.

Be willing to entertain yourself, and—equally importantly—be willing to be entertained in the least likely ways. I once found myself marooned at a wedding weekend with a crowd of Charades-lovin’ folks and, while I was a bit daunted and disconcerted at first, I had a surprisingly fun time with my miming crew. (I also discovered that I possessed an almost savant-like ability to decode very random “clues” which made me unexpectedly popular amongst the In Crowd, which just goes to show—you never know, and you should always be prepared to discover hidden talents or hidden depths within yourself.)

The long and the short of it is this: Both guests and hosts alike have the duty to compromise without complaint, and to be open to new perspectives, points of view, favorite games…and who knows? Maybe you’ll find out that you really do have an affinity for board games, or ice-skating, or tropical fish viewing. Maybe you’ll enjoy learning to make your own noodles, or to weave lanyards (kids just back from or on the way to camp love to fashion these, and if you’re not careful, you’ll find yourself looping and braiding along with them). And maybe…just maybe…during these times-out-of-time, away from the daily grind and pull of everyday life, you’ll discover within you what it means to be a real and true friend. And that is something which money surely can’t buy.

The Kids Are All Right (Sometimes)

For many of us, long weekends away (or even longer vacations) involve staying with and/or bringing children along. And as lovely and charming as the average 8-year-old can be (and I speak from experience here), somehow their idea of a really storming time, and your idea of beachside bliss, rarely coincide. The fact of the matter is kids like action. And ice cream. And role playing, often with props. This is a tricky area—if you’re the guest who doesn’t have kids, you’ll want to make sure the little ones like you enough, but not too much (it’s a dangerous thing to be too cool—and if you’re not careful, you never will get to work on that backhand, busy as you’ll be hangin’ with the kids). Luckily, eternal devotion can be yours if you bring a reasonably cool toy or game to give as a gift, and come prepared with a few tricks up your sleeve to teach them (in my crowd, there is a dad who can tie a cherry stem in a knot with his tongue, and he’s kept hordes of children silent over the long dinner hour by challenging them to learn how to do it. I myself have a never-fail riddle that can last over at least two courses, but I’m not telling it to you!)

If you’re the guest who has kids, it’s your job to make sure that they have an exceedingly firm grasp on the ground rules before you arrive, and that they understand that moaning, whining, or complaining will end their fun, pronto. Also, be prepared to pay for babysitting—I actually advise this even if you’re eating in—a local nanny or sitter will be miles more entertaining to the under-13 crowd than will cold pizza and a movie in the spare room. This is money well spent, and should be factored into the cost of the trip.
Final thoughts? Don’t forget to have fun. It can be too easy to stress out about any and everything, and before you know it, your getaway has got away without you. Relax: They like you, or they wouldn’t have invited you in the first place. So just be yourself…with your own lovely manners, of course.