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The Ultimate Guide to the Best Guys’ Trip in Vail


Welcome to the trove of information you’re going to need to make it happen — and because you clicked on this blog post, you all know what “it” means. And it’s going down in Vail. If, however, you found us online by Googling “mancation,” you may go now. This here is a jam for all the fellas.

Take a couple of deep breaths and pat yourself on the back because you got the crew to commit. This is a guys’ weekend we’re talking about, not sophomore-year spring break at a small ski area in New England. You got your band of brothers to say “heck, yeah.” You negotiated a week away not only with your diverse group of friends, but with their partners, their bosses, their kids, their pets and several mothers-in-law. Hi-five.

Now, it’s time to get a move on and start planning. We’ve got the 411 to ensure that this won’t be your last guys’ weekend in Vail.

Arrive in Vail

If you got here by searching “how to get to Vail,” then do yourself a favor and call a travel agent. For the rest of y’all, you know what to do. This is your crew, and they all know how to book flights direct to the Vail/Eagle Airport or Denver International Airport, grab a shuttle (or hire a private car service) and head to Vail. They’ve got this covered.

Do, however, have a list of everyone’s flights and info. Just use your favorite flight/trip tracker. You know, the one that you stopped using in 2020 and paid for until this past February? Yeah, that one. Turn it on again and start tracking. That way, when a quorum has arrived, you can bet on flight arrival times just like Kramer and Earl Haffler!



It’s a men’s trip to Vail. With all due respect, you don’t go small on this one. No matter what your speed — luxury private residences, villas, condos or suites — you’re going to need some space. Where else are you going to take all of Bob’s money playing ill-advised games of no-limit hold’em while watching Rounders? You’re men now. Do you really want to listen to Jeff snore? Or share a bathroom with five guys? Go big. You need a stunning mountain view, a comfortable living room, an amazing bed in a quiet room, and a kitchen or a suite with a clawfoot tub filled with ice. (Side benefit: Someone might need an ice bath after a full day on the mountain.)

Get After It

On Vail Mountain

Skiing with the guys is a whole thing. Eliminate the drama (and a lot of “angry dad” voices yelling across Siberia Bowl) that comes with everyone trying to “stay” together.

You didn’t come to Vail for the drama so hire some private instructors for the group. Your private instructors will get your group to the best possible spots on the mountain based on your skill levels, time of day, snow conditions and grooming, the weather and everything! From Lover’s Leap in Blue Sky Basin to the little know stashes of powder in Northwoods to the intermediate groomers on the front side that seem to go on forever — they know it like the back of their hand. Plus, you don’t have to wait in lift lines. This is why you came here, so don’t skimp.

Pick a time to meet together for a late lunch. Make a reservation at The 10th at the top of Gondola One. No need to check out the reviews on Yelp, this restaurant is a lock to impress your buddies. Roll in and peel off those stiff, cold ski boots that are eating your shins and don warm slippers. That’s right, I said “slippers.” Not only is this location ideal for a meet-up, the staff incredible, the energy amazing, the drinks top-notch and the food perfection, but they also have complimentary slippers. And it’s appropriate to wear them at the table in a place you may have only dreamed about when you were 20 while eating at Wendy’s. Also, you will likely lose 50% of your on-mountain crew after lunch. No worries. Hot tubs are cool, too.

Other Adrenaline-Filled Adventures

Spend at least a day all together because there are so many amazing group activities to take advantage of in one of the most spectacular places on earth. It will give you all a chance to do something adventurous and, for the part-time skiers/riders in the group, it’s a great break from trying to keep up on the hill.

Depending on the length of your stay, you’ll need to prioritize. Choose the best activities that suit your style and book them in advance. Nothing makes a man trip run more smoothly than guaranteed fun reserved in advance.

Snowmobiling Near Vail

Not much can compare to a day spent out on a snow machine in the vast Colorado wilderness with friends. Take a day-long excursion with the pros at Nova Guides, and experience a part of history by snowmobiling at Camp Hale, the country’s newest designated national monument where members of the famed 10th Mountain Division trained in 1942–43 before heading off to Europe in WWII. It makes for a once-in-a-lifetime ride.

Another great option is to book a private tour with the amazing people at Sage Outfitters, who offer a private snowmobile playground with hundreds of miles of custom-designed trails — the most in Colorado.

Ice Climbing in East Vail 


If you still get a chill every time somebody takes out an ice axe in Cliffhanger, spend the morning scaling frozen waterfalls in East Vail with the climbing experts at Apex Mountain School.

Fat Biking Around Vail


This might take some explaining on your part because going for a bike ride on a guys’ ski trip sounds pretty far out there, but something that shouldn’t be missed. Spend the afternoon fat biking in and around the mountain, over the river and through the woods.

Recover: Experience Vail Spas & Shops


Let your crew have a chance to relax and give some TLC to those aching muscles that serve to remind you that you are living life to its fullest. Spend the afternoon at the spa to rejuvenate your body and mind. Hit the iV Bar at The Ritz-Carlton and recover from the elevation drain and the previous evening’s revelries. Whatever you do, set time aside to recover. Unless you plan on taking a vacation after your vacation, you’re going to need to be functional when you get home!

Speaking of going home, now would be a great time to thank that special person in your life who made it possible for you to goof around with your buddies. Head into the village and hit the shops and boutiques to bring back a unique trinket from Vail. Don’t be that guy who scrambles to get something last minute at the airport because that dude won’t get to do this again for a long while.

Eat, Drink & be Merry: Vail restaurants & Nightlife Tips


No guys’ snowboard trip can be complete without an exhaustive list of places where you must eat, bars you can’t miss, and the greatest après locations imaginable. That book has been written, and no sense in abandoning your go-to social media ratings and review sites just because you’re in Vail. Go ahead and do a little research, but then let serendipity take over — not everything needs to be planned and you really can’t go wrong with any restaurant or bar in Vail.

What does need to be planned is an amazing dinner. If you want to visit some of the best restaurants in the Rocky Mountains (or anywhere), make sure to figure those out well in advance. Don’t expect to roll into Sweet Basil, Mountain Standard, Elway’s or Matsuhisa with a group of dudes on Saturday night and expect a table. Reserve at least one fantastic spot for dinner when you book your stay. No matter what you do, there are some things that you cannot miss while in town.

  1. Live music at the Red Lion.
  2. People watching at Pepi’s.
  3. Hanging with locals (and pretty much all of Vail Ski Patrol) for pizza and beer at Vendetta’s.
  4. The miracle hangover cure that is the Pannekoeken during breakfast at The Little Diner (send your anxious friend to check in and wait for the “your table is ready” text).
  5. If you’re lucky enough to be able to stay on a Sunday, catch the games and talk fantasy football league smack while bowling at Bol or drinking beers at the legendary Garfinkel’s.

Now close out the hundreds of browser tabs you’ve been keeping around for this epic event (except this one), #hydrate, and get after it. Be safe and have a blast — you all deserve it!