St. Regis is the choice. Aspen is a real vibrant city compared to Vail which is a pretty artifical village.

Skip Breckinridge. Vail and Aspen both have more to offer. Vail is a make believe town copied after a Swiss village (Zermatt maybe)sort of how you would think Disney would have done it. More conservative than Aspen - full of the button down corporate CEO types. But it has awesome skiing, dining, lodging, golf, etc. Aspen is more edgy - trust fund hippies and Hollywood types mingling together. Aspen is a real town and has knockout scenery but expect some attitude. Visiting both gives you a great contrast.