Website: skiportillo.com

From the weirdo "slingshot" lifts to the views of 20,000 ft. mountains all around, Portillo would be an epic place to take your girlfriend for an original late summer/fall holiday. Underrated Chilean wine, great riding when the snow and wind cooperate, and friendly staffers who've often worked here for 40 years or more. Plus, they limit the number of people on-hill so it's not such a NASCAR race at the end of the day.

Snow Bunnies Decent Nightlife