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Plan Your Trip

Book online or call 888-500-5155 (+1-970-496-4910) to speak with a local expert.

Guys Weekend Itinerary

The seemingly endless terrain, seven legendary Back Bowls, more groomed terrain than anywhere on earth, even our iconic alpine villages, they're all here waiting for you! Discover what Vail has in store for you this winter and join us for another unforgettable ski vacation. All you need to bring is your favorite people, we've planned out your perfect getaway from the time you arrive to the time you leave. 

See our itinerary recommendations and experience the Best of Vail This Season!

Ready to enjoy another perfect getaway to Vail? Discover what luxuries await you at our countless lodging properties.


1. Arrive, get ski equipment and passes

You made it! Since you already bought your ski passes and pre-booked your equipment reservations, this part will be a breeze. We’ll even deliver your equipment to your hotel and you can leave it with the very convenient ski valet at The Lodge at Vail or The Arrabelle for the evening. Get ready to start exploring.  

2. Book private ski guide to explore Vail’s variety of terrain

Vail boasts 5,289 skiable acres, which is a good deal more than you’ll be able to cover in your few days here. Book a private ski guide so you can explore parts of the mountain you’ve never seen. Whatever terrain you’re aching for, our guide will show you Vail’s hidden gems.

3. Dinner in Vail  

Drop off your gear and head to dinner. Feeling carnivorous? We recommend the Vail Chophouse or Flame at the Four Seasons for your first night here. Both restaurants offer hearty surf and turf options and large sides to satisfy even the hungriest of appetites.

4. Drinks

Time to wet your whistle after gorging on some grub. The Red Lion and Shakedown both offer live music nightly, along with a very lively crowd. Try one of Red Lion’s “Winter Warmers” or a refreshing draft beer at Shakedown. 


1. All-day ski

Grab your gear from the ski valet and get on the mountain! Your guide showed you the ropes yesterday, so now it’s your turn to explore Vail’s variety of terrain with your buddies. Try out the Back Bowls or take on tree skiing in Northwoods. Cross your fingers for fresh snow, drink plenty of water and eat a big breakfast – you’ll be skiing hard today. Track your vertical feet with the EpicMix App and earn badges as you make your way around the mountain. You can even race your buddies with EpicMix Race, a course that’s been run by Lindsey Vonn.

2. Après in Vail

Nothing beats drinking your first après sip after a gratifying day on the slopes. Post up at either Vendetta’s or Los Amigos, two of the liveliest and most popular après spots in town. Mingle with Vail ski patrollers at Vendetta’s or watch people finish their last run of the day on Los Amigos’ deck while sipping on some ice-cold beer.

3. Dinner in Vail

You can stay at Vendetta’s for some pizza or walk over to Pepi’s for authentic Austrian fare. Pepi’s has been family owned and operated since 1964, serving up traditional items such as Wienerschnitzel, as well as Colorado-inspired dishes, including rack of lamb.

4. Explore Vail’s nightlife

You’re already on Bridge Street, which is primed for barhopping. Take the party to one or many of the nearby options, from the 10th Mountain Whiskey & Spirit Company to The George and countless others. Bonus: Vail’s free in-town bus runs until closing time, allowing you to imbibe into the wee hours of the morning. 


1. Half day ski

Now that your ski guide showed you the ropes, you’ll be ready to tackle other parts of the mountain with your group. Make a game plan before you get on the slopes using Vail’s 10 spots for expert skiers and riders.

2. Late lunch at Wildwood Smokehouse on mountain

BBQ is best served miles high. Wildwood Smokehouse sits at 11,000 feet high at the top of Wildwood Express and Game Creek Express lifts with great views and award-winning smoked sandwiches.

3. Hot tub time

Take in the gorgeous sights and relax your muscles in the hotel hot tub to unwind after racking up thousands of vertical feet over the past few days. Then grab a drink before dinner at the hotel bar as you toast a memorable weekend.

4. Dinner in Vail

Close out your last night in Vail at either John Elway’s namesake restaurant or Vail’s original prime rib house, Lancelot. Elway’s specializes in aged, USDA prime beef and also serves delicious fresh fish. You also can’t go wrong with the specialty prime rib at Lancelot, which has been slow roasted to perfection the same way since 1969. 


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