How To Plan the Ultimate Boys (or Girls) Ski Trip This Winter

(Authors note: ‘boys’ can be substituted for ‘girls’ throughout the article)

Whether you’ve been doing it since your teens, 20s, 30s, 40s, or even if this is your inaugural year, the annual boys ski trip is a highlight on everyone’s calendar. For some of the group, it may be their one week or weekend to get away and have some bro time; for others, it is just a highlight week in a season packed with fun. Either way, it’s a special trip that creates memories and camaraderie, helps build great friendships, and should be incorporated into your crew no matter how old you are.

What makes the boys’ ski trip special goes beyond skiing and snowboarding. There is something to be said about being packed in a house or condo with your friends, waking up early to grab first tracks, and staying up late to get those last shots of Jager in. Building traditions and inside jokes that carry over from year to year easily take away from the monotony of the daily grind and create an early-season excitement when the group chats and emails start, and the planning goes into effect. The strategy, planning, and occasional smack-talking that start way before the actual trip ARE the actual start of the trip if done right!

There are many ways to plan and organize your trip, including lodging, food, travel, resorts, or participants.  My group of 6-10 “boys” have been doing this for as long as I can remember, so here are some of my essentials, favorites, and recommendations as you start to look ahead to this winter. Use at your own leisure and risk:

• Start Planning Early: There is nothing wrong with starting your discussions in late August or early September.  In fact, depending on the size of your crew, it may be necessary to secure lodging for your desired week, as high-traffic weeks and premium lodging are getting booked earlier and earlier every year.  Use apps like GroupMe or Facebook Groups to get the conversations started, smack talk going, and polling to make group decisions. Keep it going up to and through the trip to share pictures and stay connected. Starting early also gets everyone pumped for the season and is a good annual tradition to mark the transition from summer to fall.
• Choose Your Destination Smartly: Figure out who has what passes and pick destinations accordingly.  Epic and Ikon passes open up nearly any state or region and help shave hundreds of dollars of the trip cost for those who have them, better yet coordinate on passes in the spring or summer based on your desired destination(s).  Look at ease of travel for the crew…where are people driving or flying from, how easy is it to get from airport to lodging, or lodging to resort? Have you done the trip before? Since snow can be the wild card, what are the trends for that time of year?  Look at other events going on at the resorts, races, festivals, or on-hill events. There are many towns that have kick-ass concert venues like Park City’s Park City Live, Jackson’s Pink Garter Theater, or Aspen’s Belly Up.  One of my favorite weeks was planned around a 3-night set by Lucero at The Sitzmark (aka The Sitz) in Alyeska; seeing one of your favorite bands in the base bar after ripping top to bottom runs changes the whole dynamic of the experience.

• Find a Great Place to Stay: Figure out what is important to you. Is it the number of beds, proximity to slopes, budget, or room service…with the online booking tools for hotels, Airbnb, VRBO, etc., you can find a place that fits your needs, but you should book as early as possible for the best deals. With vacation rentals, you are likely to have the most options when it comes to size, ability to cook, stocking up on provisions, and comforts of home.  Planning your arrival should also include a trip to the local market for the essential drinks and snacks. A fully stocked fridge is sure to make everyone feel right at home.
• Choose Your Crew Wisely: Most of us have a core of guys we go with every year. These are the backbone of your trip. Invariably, new guys get invited to the trip for a trial year. From experience, it’s super important to vet the new additions to make sure they are a fit before they accompany your crew.  Do the new additions fit your style on and off the hill?  It’s ok if they are not rippers, but is there someone that matches them so you’re not chasing a lone wolf at the end of the day. Do they match your apres, dinner, and nightlife style?  We’ve had many an add-on get vetoed after year 1 because they preferred staying in vs. crushing Jager bombs til last call, or were more Kraft Mac n Cheese vs. nice dinners.  If they are not a fit, be sure to give their sponsor-friend tons of crap about it! It’s important to keep your group dynamics cohesive and consistent.
• Get Organized: A shared spreadsheet like Google Sheets (Sample Sheet) can really help with keeping the trip and its participant’s info in one place.  Keep all contact info front and center; share flight info so you can coordinate transportation; keep track of lodging addresses, numbers, and dates; put restaurant reservation information there; initial costs and who has and hasn’t paid (publically shame those who are laggards in paying) basically a one-stop-shop for all your trip info so everyone is on the same page…no excuses from anyone, even the one friend who always pretends to be in the dark.
• Manage the Finances Smart: Sharing costs on a big group trip is no joke; it can ruin a trip (and sometimes a friendship) when someone does not carry their weight.  Decide what costs you are collecting upfront and follow through, even if it means just taking a deposit.  Your lodging choice is usually based on how many bodies are expected and it’s ok to adopt a deposit policy even among friends, it shows commitment and keeps everything square.  Use apps like Splitwise or Venmo to get everyone paid on time and minimize cash changing hands (always a clusterf*ck).
• Make Dinner Reservations Before You Travel: This is especially important for larger groups and track in your trip spreadsheet, including links to the menu.  Trying to coordinate dinners last minute usually means you’re stuck with whoever has seating or waiting for a table where none may be available.  If you like fancy, great, do your homework, get on the website, and book those tables.  Make your reservations according to how your group behaves; if you crush apres-ski shoot for a later time, if you are staying in, book the earlier time. And for the love of all things holy (or unholy) about ski town living, if you double book, don’t be an ass…cancel at least 24 hours early so someone else can take your spot.

• Don’t Be Afraid to Plan a “Down” Day: A down day off the hill can mean anything from a snowmobile adventure through Yellowstone to shopping in town, relaxing in the hot tub, or even booking a cat or heli day (I guess that would be an up day!). What a down day means to your crew will vary based on fitness level, budget, and areas of interest, but diversifying from the resort can be a good day to bond and catch up.
• Look For Local Discounts: Looking to save a few dollars here and there? The town papers are usually filled with specials for gear, food, and other amenities. You can also find discounts on some restaurant websites. For example, Shabu in Park City offers 33% off dinner or lunch, Gather in Jackson Hole features a Happy Hour from 5-6 (Crispy Brussels Sprouts are amazing), or The Auld Dubliner in Squaw Valley’s Village features a happy hour from 2-5 with a rocking PBR and crispy fish taco for only $6.  A little research can go a long way towards shaving some costs off your total expense.
• Have Fun: You’re not at home or at work, so live it up. Contrary to what mom told you it is ok to talk to strangers, you never know who you’ll meet. You could merge with another fun group and have an evening to remember.  Make t-shirts or hats to commemorate the trip, and wear them proudly. Have theme nights: flannel night, grow mustaches for the trip, green t-shirt night, mullet night, play drinking games, or have scavenger hunts…be as mild or wild as you want to be both on and off the hill.

Making the boys’ ski trip a ritual and an institution ensures your bonds grow over time and gives you something to look forward to every year. Stay committed and let it grow; try to fit in a golf week or motorcycle week as your work, time, spouses, and kids allow.  Acting young keeps you young, and your coworkers will get jealous and envy your life. With proper planning and the right attitude, the perfect boys’ (or girls’) ski trip can be right around the corner. What are you waiting for?