Bal Harbour Shops

For golfers, the Hamptons occupies a near-mythical status. Part of that is the golf itself, of course, but much of the intrigue comes from what remains just beyond reach. Membership at many of the area’s most sought-after clubs is famously difficult to secure. Waiting lists stretch for years. Existing members sponsor candidates. Vetting can feel more intensive than a college-admissions process. Even then, nothing is guaranteed.

Though it may have been put on the map for its ski—and inimitable après ski lifestyle—summer might be Aspen’s true season. The mercury will rarely hit higher than the mid-80s, and the dry, warm weather makes it ideal for every outdoor hobby. Paraglide off the mountaintops, for example, or take an al fresco yoga class; there’s mountain biking, e-biking, while avid hikers should tackle the challenging Buckskin Pass, which offers superb views across the Elk Mountains.

If one wants to understand what makes the Northern Sonoma town of Healdsburg so singular, it begins with the land itself. Healdsburg sits at the convergence of three major wine-producing valleys: Alexander, Russian River, and Dry Creek. Here, varied soil and shifting micro-climates shape not only the grapes, but the wider agricultural bounty that has long defined the region.