The hopelessly out-of-date stretch pants I wore the first time my boyfriend and I went skiing were very tight. They were the same navy blue pair I'd bought in high school, back when Bon Jovi was big time. Yes, they still fit me, and no, they didn't look good. I knew I was really in trouble when the teenager at the ski resort's rental desk was not only unimpressed by my request for "a pair of 180s," but politely explained that they don't make skis like that anymore.

And that's not even the most embarrassing part.

The teen cracked up when she saw the stirrup pants tucked into the ski boots and said, "Um, I don't think that's how pants are supposed to go."

The next time we set out for snow, I chose snowboarding instead. I had a new pair of XL powder pants fresh from the children's section of Target, and an Old Navy parka. Both cost less than 20 bucks and both worked perfectly (more on this later). Since I'd never snowboarded before, I took a group lesson, let my snowboarder boyfriend show me a few more moves, then enjoyed the rest of the day on the slopes. This was the positive experience I'd been hoping for -- no one was embarrassed; no one felt ill-equipped. And though I was a newbie boarding with someone who'd blazed all over the French Alps, I had a great time.

That's the experience I want for my young family when we start taking snowbound vacations. Since I've obviously had mixed experiences, I asked a few experts to weigh in before I hit the slopes again with the same swift snowboarder -- now my husband -- and our three kids.

Good: Start Local

If your trip will mark the first time anyone in your family has ever hit the slopes, keep it simple. Find a resort within driving distance, and here's the big thing: Make sure your room is close to the lifts. "A family trying skiing for the first time needs to consider centrally located accommodations close to the slopes," explains Sheila Chapman, PR manager at Big Sky Resorts in Montana. "It's all about location." Chapman says it's ideal to find a ski school close to children's activities and lodging, too. While these rooms may cost more, the convenience is worth it -- especially for a family who's likely to be wiped out from... well, wiping out all day long.  

Chapman's second tip? "It's highly recommended that parents and children sign up for lessons, even if the parents have skied in the past," she says. "Ski and snowboard technology has advanced, and so has the skill set." Most resorts offer ski lessons to kids as young as 4, and snowboarding lessons for those 7 and up. 

Finally, check into what other activities are available. From day or night childcare to off-the-slopes activities, make a game plan with contingencies ahead of time. Someone in your group is bound to get tired or cold and want a respite by way of indoor pools, waterslides, movies or good ol' game rooms.

If this sounds expensive, there's good news there, too. Most resorts have family packages that actually mean savings when you sign up for rooms, lessons and rentals together -- and sometimes there's even a spa treatment involved.

Which leads to the question of gear. For first-time skiers, buy only reasonably priced outfits -- must-haves are snow pants, parkas, long underwear, gloves, socks, boots and hats -- at places like Target, garage sales and thrift stores, or simply borrow from friends. Don't forget snuggly sweat suits for evenings. If the kids fall in love with the slopes, upgrade. Otherwise, it makes more sense to rent all your gear. You'll have up-to-date skis or boards sized perfectly according to each person's weight and ability, without paying full price for things you may not use again.

Better: Get Good Gear

If your family has been on the slopes several times and you want to take your act on the road, good for you! "An active vacation like a ski trip provides a great opportunity to bond as a family by doing something outdoors together," says Eugene Buchanan, author of Outdoor Parents, Outdoor Kids: A Guide To Getting Your Kids Active In The Great Outdoors. "It's a good way to let your kids strive to learn, so they can be better than Mom and Dad. They'll be building skills they can use for a lifetime."

And there's no better place for a little family competition than a highly rated family ski and snowboarding resort. Topping nearly every "best for families" list in the U.S. are: Steamboat Springs in Colorado, Big Sky Resort in Montana and Smuggler's Notch in Vermont -- where kids' lessons include pirate sing-alongs and wacky science shows.

It's still good to situate yourselves near the slopes, but if your crew is more advanced, consider a more involved lesson plan. "Parents who are intermediate or better skiers can try our Mom & Me/Dad & Me lesson, where the parent works in tandem with a ski instructor," says Karen Boushie, PR Director for Smugglers' Notch Resort. "The parent comes away with tips that they can continue to use as the child progresses."

At this stage, you're likely to have your own gear, and if it's in good shape, it might be worthwhile to check your skis on the plane, rather than renting them upon arrival. Inquire about package rates from the resort first.

Best: Go Exotic

If your family knows and loves the slopes, this could be your year to do it up to the max at an exotic locale, like Alaska or the Alps.  

What's so special about the Alps? The terrain is vast, with just as many challenges at lower altitudes as at higher ones. Then there's the cultural aspect. Vacation with any French person, and you're bound to have a great culinary experience as well. Packages in the Alps are likely to come with a chef, or at least an award-winning restaurant, to leisurely stroll in and out of before and after runs. And don't forget the incredible juxtaposition of historical villages sprinkled with lifts using cutting edge technology.

European resorts on many "Best Ski Resorts for Families" lists include Morillon in Grand Massif, France, and Zermatt in Switzerland. Austria's Zell am See resort consists of 93 acres of runs overlooking a blue glacial lake, plus a village founded by eighth-century monks. Snowboarding through history is an incredible way to spend a week with family.

Or, you all could head to Alaska for another trip of a lifetime. Family packages range from leisurely on-and-off again cruises to adventures atop the snowy slopes of volcanoes. As if the lifts weren't enough, most resorts include options for snowshoeing, snowmobiling and even zip lines. This is the stuff of "remember the time we... ?" conversations, says Boushie. 

No matter which slopes you decide to hit, don't forget that it's all in the name of a good time. "Let everyone proceed at their own pace," says Buchanan. "Don't put any preconceived notions on your kids as to how good they should be. The point is just to go out there and have fun."