Tips for Planning Your Ski Vacation

Tips for Planning Your Ski Vacation

Published by Brion O'Connor

How to Plan a Great Trip.

Skiing is a blast. Traveling to find new ski experiences can be a blast as well, but it can also mean headaches. A ski vacation – especially one that involves air travel – is obviously a whole lot more complicated than picking a resort and a date.

So, to make sure you can focus on the fun, accentuating the positives while minimizing the negatives, we decided to get some expert advice from Lisa Leavitt, co-founder of the Boston-based Active Travels.

Ski resorts/lift tickets

Much like buying season passes at your favorite local resort, the sooner you can lock up your ski passes, the better.

“Look for deals on lift tickets online at the ski resort, or Liftopia, and realize that mid-week is also better for pricing and shorter lift lines,” said Leavitt. “If you really want a deal, head to Canada, where Americans can still get a favorable exchange rate.”

Other solid online sites include,,,, and Many sites also incorporate last-minute deals, and lodging packages. Don't be bashful about calling the resorts to negotiate better deals. Of course, if you have an Epic, Ikon or other multi-mountain pass, you're ahead of the game.

Of course, buying your lift passes months ahead of time requires a certain leap of faith, and accepting the risk that the conditions may not be ideal when you vacation finally arrives. In early February 2016, I met a couple from Quebec as they arrived at Killington ski resort in Vermont, during one of the worst snow droughts ever in New England. There was precious little snow on the slopes, and what was there was mostly man-made (a testament to Killington's legendary commitment to snowmaking). The couple was disappointed, but not crestfallen.

“We'll just make the best of it,” said the husband, referring to another crucial aspect of ski vacations – perspective (more on this later).

Timing, in terms of when you're traveling, is also critical.
“Book well in advance for December, Martin Luther King Weekend, and February and March school breaks,” said Leavitt. “Those are the toughest time of year to find good lodging. The rest of winter is far simpler.”

Keep in mind that the school vacation weeks in your state may not correlate with the state you're traveling to, or even other states where skiers are looking to get away. For example, New Hampshire and Massachusetts don't have the same winter vacation week, in part to allow ski resorts to accommodate skiers and boarders from each state without getting overcrowded.

Depending on how particular you are, take a close look at the resort's rental ski situation. I love trying the latest skis, provided I have the option to switch out my rentals if a certain pair doesn't feel quite right. By comparison, I always bring my own boots, do to my accumulated orthopedic issues, and helmet. That also allows me to pack more clothing, which given the vagaries of Mother Nature and ever-changing winter conditions, is always a wise move.

Traveling to a spot like Salt Lake City in Utah, which offers at least a half-dozen world-class resorts within a short drive of the city, has some superb ski rental shops in town, and satellite outlets at nearby resorts. That's the best of both worlds, in my estimation (just make sure you reserve your gear well in advance; there's nothing worse than having a poor selection of equipment once you arrive).

“If you can’t live without your precious skis and bindings, bring them,” said Leavitt. “Otherwise, most top-notch ski resorts have great rental equipment these days, and even the chance to sample real quality gear on the many Demo Days.”

If you do bring skis make sure to check with the airline’s baggage policy. Also to protect your gear, be sure to pack it in a fully padded ski bag; and if bringing two pairs of skis, a double roller ski bag will make traveling far less challenging.

Speaking of Salt Lake City, Leavitt pointed out one mistake that she sees ski travelers making all the time – trying to do too much. Specifically, she warns against trying to squeeze a visit to every mountain within a one-hour radius over a three-day to one-week span.

“They come back exhausted,” she said. “Choose one or two peaks, and don’t worry. You’ll hit Alta next time.”

That approach, she said, allows you to really get below the surface when exploring an area. For example, when flying into Salt Lake City, decide on Little Cottonwood Canyon (with Snowbird and Alta), Big Cottonwood Canyon (with underrated gems like Solitude and Brighton), or Deer Valley and Park City/The Canyons in neighboring Summit County.

By the way, booking a lesson at a new resort is also a great way to get a free tour of an unfamiliar mountain (since you're essentially paying for the instruction).


In addition to finding a great deal on the cost of lodging, there are other important factors to consider. As the time-honored real estate maxim “location, location, location” suggests, where you're staying should be part of the vacation-planning equation.
“Ski-in, ski-out properties are worth the extra money, especially when traveling with children,” said Leavitt. “That saves you so much time and effort in getting out on the slopes.”

The younger your kids, the more true that statement is. And, speaking of kids, keep in mind that skiing is only part of your ski vacation. Remember the couple from Quebec that I mentioned earlier? Having a resort that offers myriad activities – from pools and climbing walls to fitness facilities and ice rinks – is a great hedge against bad weather.

But even if the snow conditions are perfect, the variety that other amenities offer can make for a more enriching experience. My daughters, wife, and I have enjoyed dog-sled rides, snowshoeing or snowmobiling adventures, ice climbing, and even cooking lessons during our winter escapes.

“Give yourself time to sample all the other activities on the mountain besides downhill skiing, like tubing, zip lining, and, of course, the requisite horse-drawn sleigh ride,” said Leavitt. “A spa treatment, like a deep-tissue massage, is another luxury you should treat yourself to after several days of skiing.”

She's right. Two decades ago, during a trip to Sugarloaf in Maine with my in-laws, the weather turned nasty. A driving rain, followed by bone-chilling temperatures, transformed our favorite slopes into a Red Bull Crashed Ice course. Our saving grace was the resort's Sports & Fitness Center, where we spent some time at the pool, and my wife and I got a massage.

Leavitt's point about slope-side lodging also allows folks to immerse themselves in a multi-faceted base area like Whistler in British Columbia even after the lifts close for the day.

“Take advantage of the après-ski scene, where you get to meet skiers from around the globe over local craft brew, often with live music,” she said. “It’s the perfect way to end your day of adventure.”

Air travel

Again, the earlier you can plan your travel, the more likely you'll get a better price. The flip side, especially if you're single or part of a couple and have more flexibility in your schedule, is the killer deals you can get at the last minute. Even though Labor Day has come and gone, it's not too late make those phone calls or Internet searches.

“You’re still early” in terms of planning, said Leavitt. “People start to get excited once the ski show hits town in Boston, usually early November. But this time of year, everything is wide open.”
However, Leavitt offers one major caveat, which again I can vouch for based on first-hand experience. “Be careful of flying into small airports like Aspen or Telluride (in Colorado), because those flights are the ones cancelled more frequently,” she said. “Better to fly direct to Denver and drive.”

The drive will also help you acclimate to your new surroundings, reducing the risk of that bane of ski vacations – altitude sickness. And many major airports in ski country also offer van services, allowing you to skip the stress of driving altogether.

Granted, Colorado's I-70 can be a bit of a crap shoot, especially by the Eisenhower Tunnel near Loveland Ski Area, some 60 miles west of Denver. That's one reason I always rent a 4-wheel drive vehicle. But as sketchy as the roads can be, I've never gotten stranded. I can't say the same for Aspen.

Also, drawing on my own history, always check to see how many fights your carrier has coming in and out of an airport. I once got stuck in Boulder, Colorado, because the airline I was flying (which will remain nameless) had only a single daily flight heading out of Denver. So when a big storm shut down Boston, my siblings and I got bounced for three days waiting for room on a flight (through one brother and my sister got partial refunds for switching to a different carrier, allowing them to get home earlier).

Group travel

Ski vacations can also make for wonderful group outings, whether a family get-together or a collection of friends (think Girls' or Boys' Weekend). As the old adage goes, “the more the merrier.” But that adage doesn't necessarily apply to the planning process, said Leavitt.
“Always let someone take the lead and put together the package, whether it’s a multi-generational trip or a girls getaway,” she said. “It’s like that saying, 'Too many chefs in the kitchen.' It's much easier for one person to set up the whole ski package and present it to the group.”

The key here is to select a point person who excels at compromise, someone who can take numerous ideas, find the common ground (including any budgetary concerns), and then sell the program to everyone in the group.  Ideas on where to go.

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Image: Timberline - Mt Hood.

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