Fall Travel Guide: Custom Weekends: Live Like the Blue Bloods

Sitting harborside on the sweeping lawn of the Wauwinet inn in Nantucket, I was thinking of Rose Kennedy. As I lounged, surrounded by the fortifying navy-blue waters of Cape Cod, I mused: Was it any mystery why she lived to be 104?

All the New England trimmings are here: the cobblestone streets, the white church steeples, row upon row of tidy shaker-surfaced bungalows. It’s the Shore manufactured by Ralph Lauren.

Sitting harborside on the sweeping lawn of the Wauwinet inn in Nantucket, I was thinking of Rose Kennedy. As I lounged, surrounded by the fortifying navy-blue waters of Cape Cod, I mused: Was it any mystery why she lived to be 104?

[sidebar]All the New England trimmings are here: the cobblestone streets, the white church steeples, row upon row of tidy shaker-surfaced bungalows. It’s the Shore manufactured by Ralph Lauren. Every woman seems to be blond, tan, trim, wearing a silk hairband and expensive capris, and named Meredith.

But while Nantucket may have Main Line style, it mercifully lacks Main Line attitude. Its cultivated air of beachy refinement (even the whaling museum is, shall we say, rococo) makes you feel fabulous without ever making you feel self-conscious about your inadequate 401K. Proudly sporting my Gap shirt, I mingled effortlessly with the Merediths while shopping in cutesy boutiques and exploring the musty bookstores in town. I topped the whole trek off with homemade ice cream at the oddly named Juice Bar, which as far as I can tell sells almost no juice. (Although the Merediths do suck down Diet Cokes.)

Mercifully, I hadn’t come to diet: The six-course tasting menu at Topper’s, the Wauwinet’s restaurant, left me feeling I could be an exhibit at the aforementioned whaling museum, with a Georges Perrier-worthy lineup that included an appetizer of Kobe sirloin carpaccio served with truffled popcorn. The equally charming White Elephant may be one of the most romantic inns anywhere, a Pottery Barn-esque mélange of over-upholstered chairs, white wainscoting, French doors, fireplaces and ridiculously comfy beds.

Now I know how Rose got wheeled out for all of those “We can’t believe she’s still alive, either” birthday-candle blowouts in neighboring Hyannis. This much pure sea air, fresh food and lazy shopping can help anyone break the century mark, even if you’re not Rose. Or a Meredith.