Steven and a group of friends have been taking annual ski trips and they’ve worked out a great way to have a blast. The good news is that it’s really simple to get started!

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Here are Steven’s Steps for an Awesome Trip:

Step One: Friends

I’d advise starting with a relatively small group of 3-5 total. Our best trips were with a group of around 8-10 but unless your group has traveled before, stick with a smaller group to start. You won’t have trouble finding more people to go the next time, provided the group worked well together.

The most important, key for the trip’s success is having the right group. Easy-going and common interests (poker/board games, food + drink, and of course skiing/boarding) are good places to start.

Angry drunks that expect to be waited on need not apply. Beyond narrowing your friends to the few that will be fun and contribute to the work, consider the balance of personalities. The best parties have a mix of folks right?!?

Step Two: Destination

This part is really fun as you research the resorts. What kind of terrain are you looking for. What are the skill levels? How much can/should you each spend? How long should the trip be?

On our first trips, we’d leave on Thursday, Ski Friday through Sunday, and drive home on Monday. We all quickly realized that we were all having a great time and three days wasn’t enough to cover the mountain so we’ve added a couple days.

Now we alternate near-by and distant destinations every other year. Definitely keep it a little shorter at first because you never know how the group is going to gel.

Next you’ll need to pick the place to stay. Ask your group for preferences (we do this over beer after work one night). Consider:

  • Ski-in/out or VERY easy drive and park situation?
  • Bar/restaurant within walking distance or short drive?
  • Hot tub?
  • Total travel time (driving vs. flight + shuttle/drive to resort)?
  • Does everyone want/need their own room?
  • Kitchen required? Gas grill? Large Living Room for hanging out and playing poker?
  • Easy storage big enough for the group?
  • Are you willing to drive to the slopes (it’ll be cheaper for sure)?
  • Happening après ski scene? Or a more remote, chill locale?
  • Is there a shuttle or is parking easy?
  • Hotel, Condo, Townhouse, Duplex, Full house?
  • Access to ski a few resorts or just one? 
  • Drive there or fly? 
  • If you are flying, car rental or a resort offering good shuttles? 

Saving tips:

  1. Most resorts give discounts for advance lift ticket purchases as does Liftopia.
  2. If anyone in the group has a season pass to a local resort, check their website to see if they offer discounts at any “sister” resorts.
  3. Some airlines allow skis and boots for no extra charge if you pack them in approved bags; every airline varies so research this well. A bargain flight plus $100 ski baggage fees exceeds a moderate flight with free ski baggage.

Once the price range, needs, wants, and nice to haves are determined it’s time to book a place. I like to get this out of the way pretty early (6 months ahead is best).

You’ll have less options the closer to the travel date and a lot of places have free cancellation policies up to a couple months before the trip.

I’d also advise just taking care of it yourself or include only one other person. If everyone gets involved in finding a place, it can take a ludicrous amount of time.

We’ve used both VRBO and AirBnB.

This Airbnb (ZayLy Lodge, pics above and below) is one of the best Airbnb’s that I’ve found for a larger group. It’s crazy nice and sleeps 11 guys very comfortably (and 14 max) so the higher end price is balanced by the number of people.

4 of the 10 guys had their own huge bedroom and everyone had their own bed without using any uncomfortable fold-out couchs or futons.

Plus lots of bathrooms made life easier trying to get out the door in the morning after a long night of poker and cocktails.

Beyond awesome sleeping arrangments, the 2 huge relaxing spaces and kitchen, indoor and outdoor fireplaces and big hot tub really made the place perfect for our group.

And last, the short drive from our Seattle homes (or the Seattle-Tacoma airport) plus short drive to slopes and restaurants/bars made the whole experience relaxed.

Every group is different obviously but if you can choose a place like this one, the logistics and fun will be easy. So simple as a Happy Hour discussion, research time and booking, all the hard work is done!

Step Three: Logistics and Tips

A month or two out, make reservations for any restaurants and local activities.

Check out resort/town websites for restaurants, bars, music and activities. Make reservations for anything you may want because you can always cancel them.

Getting a table for 8 a popular resort restaurant can be rough to impossible.  We mostly grab drinks after dinner at home but if you don’t have a good kitchen or cook, this step is a must. Also, if any friends want lessons or if the groups wants to do something unusual like a snowmobile excursion be sure to reserve ahead.

Don’t over-schedule the trip though – just reserve the minimum.

It’s more fun if you’re all exploring together and there’s only a few (or no) time constraints. This is a big reason we get a place with a kitchen to avoid eating out.

Try not to be stingy.

Some people may spend more, and some less. Get over it because you don’t want money squabbles ruining the experience.

Depending on the group, talk briefly before hand about pitching in.

Many people do this naturally thank god…But similar to being stingy with money, being stingy with help will piss people off.

Stop at the nearest Costco to the resort on the way.

If there’s no Costco, opt for the best grocery store that’s well before the resort area (closer places always jack the prices up). We really don’t plan what to buy there and it all just seemed to work out. Seems like every year we get brots, buns, apples, bacon and tons of eggs.

If at all possible, bring your own boots.

They’re one of the most important pieces of equipment and they’re fitted to your feet.

If there’s not a lot of room in the car, rent your skis and poles.

It’s not terribly expensive and you’ll get to try new skis/boards. Resorts rent, but for better fit and ease use one of the online reservation companies that deliver the equipment/fit you once you’ve arrived. Check out: Black Tie SkisDoor 2 DoorRent Skis and Ski Butlers. Do a google search for rental companies that deliver along with the name of your destination resort or state.

Someone should bring a GoPro (or other action cam).

While you may not be rockstars on the slopes, it’s good to reminisce on future trips.

Bring any board games, poker sets, video game consoles that would add to the fun. Also, we’ve learned to bring any alcohol or bar tending gear needed for the group’s preferred cocktails.

Local shops gouge the heck out of you price wise and even well equipped AirBnB’s sometimes don’t have cocktail shakers or openers (because the guest before you accidentally packs them).

Check to see if firewood is cheap and easy to get (or provided).

Same as with groceries and booze, wood near resorts can be overpriced.

If driving, be sure all cars (even rentals) have chains.

If renting, figure out ahead of time where to buy chains. We almost got stranded in the Alps on our honeymoon because we didn’t plan for this.

Know that regardless of planning ahead, there will be things that go off plan. Flexibility and sense of humor are key.

Also read:

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Feature photo by Adobe, ©Happy Mom Life Lab. Article images licensed through Sarah Lukas (Steven and friend, toast, ski equipment, food, hand pouring alcohol into glass, orange tray with black gloves on it), and Inese Westcott & T. Kao (ZayLy Lodge's front view, relaxing space, hot tub), all in the context of this article are ©Happy Mom Life Lab.

Today's Guest Post by Steven Curtiss

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guy friends having a great ski vacation

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