When it comes to amazing vacation destinations that are worth exploring and enjoying year-round, Vail, Colorado has a way with scenery, fun, and outdoor recreation that’s hard to top. While Vail is always a place that deserves attention when vacation is calling, it’s particularly appealing when you're planning the best guys' ski trip this winter. Gathering your best friends and hitting the slopes in style is something everyone can look forward to when Vail is the final destination. This mesmerizing mountain town has been beckoning travelers from across the map since its first opening in 1962 and continues to captivate downhill enthusiasts to this very day. It’s earned the reputation as one of Colorado’s most popular ski destinations with good reason.
The Best Guys' Ski Trip Itinerary
With more than 5,200 skiable acres waiting to be explored across tantalizing terrain that hosts 31 lifts, there’s no shortage in the way of potential ski fun for all. Snowfall totals are impressive across Vail annually and the après-ski scene is equally intriguing. No matter what your traveling crew might consider interesting, you’re sure to find it in Vail alongside world-class ski conditions too.
When you play a guy’s ski trip this way, you’ll have access to incredible back bowls, as well as double blacks, steeps, and cruisers that are easy to pick and choose from according to ski level. From the terrain parks and rails to the half-pipes and boxes, your guys' ski trip to Vail promises to be filled with fun and easy-to-customize.
Not sure what to bring? Check out our ski trip packing list for more details!

Beyond the Slopes: Winter Activities
While it’s fair to say that a ski getaway to Vail is likely to be focused on the downhill fun, there’s more to Vail Mountain than skiing and snowboarding.
Those who are looking for a truly unique way to take to the snow will want to put their skills to the test on a ski bike while they’re in the area. These made-for-the-mountain bikes are fun to try independently, but there’s always an option to book a group ski biking night tour when a guided experience would be a preferable option.
Those who head this way for some quality time with their best buddies will find that Vail is also a great place to enjoy everything from snowmobiling and ice fishing to dog sledding too!

Après Ski Stops to Add to the Itinerary
All that time spent skiing with friends during a guy’s trip to vail this winter deserves to be followed up with some of the best après-ski stops in town too!
After you’ve had your fill of downhill fun for the day, head over to Red Lion and enjoy shot skis paired up with live musical performances! The Red Lion has long been a beloved après-ski destination in Vail and is easy to find at 304 Bridge Street.
Dusty Boot Saloon in nearby Beaver Creek is another popular stop when cowboy décor and craft beer are your après-ski style.
If you’re craving a gourmet hot chocolate to follow up the slope-side fun, make your way to Leonora Restaurant at 16 Vail Road. Here, they serve up a signature hot chocolate complete with clove spice and cardamom topped with crunch chocolates.
Local Tip: A shot of Bailey’s Irish Cream can be added upon request.

Craft Breweries and Distilleries to Check Out
If your guy’s getaway wouldn’t be complete without stops at local breweries and distilleries, you’re in luck!
Vail is home to Vail Brewing Company where craft beers abound. Their tasting room is open until 10:00 pm daily and is located at 141 E Meadow Drive #209.
Other favorites to check out in the area include:

Catch a Game on the Big Screen
For the guy’s getaway to Vail that happens to occur at the same time as the big game—there are plenty of local places that offer up a sports bar atmosphere with big screens and savory menus to match.
Head over to Garfinkel’s on East Lionshead Circle when you and your crew are looking to pair pub food and beer with mouthwatering burgers too.
Altitude Bar & Grill is another great option and provides a little more in the way of luxury complete with a 100-foot projection television.

Live Music Venues to Enjoy
When you can’t wait to end your day on the slopes with some live musical entertainment, Vail offers up a variety of places to enjoy.
Los Amigos at 400 Bridge Street is a great stop when you’re craving authentic Mexican and the music to match!
Bridge Street Bar at 304 Bridge Street has DJs take to the stage until 2 am many mornings. Keep in mind, they're closed on Mondays!
Red Lion is always a fan-favorite stop for live music as well. Planning to visit? Check out their Events Calendar online before heading over!
Don’t leave Shakedown off the list when you’re looking forward to dancing and rocking the night away on Friday and Saturday nights only!

Book a Stay at Lodge at Lionshead & Enjoy Amazing Amenities
For all of the fun, adventure, and amazing downhill opportunities Vail offers guests who are traveling this way for a guy’s ski trip, having amazing accommodations in place can elevate the experience even further. Be sure to book your stay at the Lodge at Lionshead while you’re here!
Whether you’re looking for studios to rent or require property options that host up to 4-bedrooms, you’ll find what you’re looking for and more. Those who book one of these inviting and spacious condos will also enjoy access to the lodge amenities for guests including:
- Everything from heated pools and a full fitness center to on-site hot tubs
- Concierge services
- Ski and snowboard equipment storage options
- And, complimentary snowshoes upon request for those hitting the snowy trails.
Individual condos at the Lodge at Lionshead for your guy’s ski trip to Vail include features like:
- Fireplaces
- Private balconies
- Full kitchens
- And, high-speed internet.