1 The Beachy Nantucket Weekend.
If the White Elephant is sold out, try the Jared Coffin House.
Forget about scoring a beachfront room on Nantucket this late in the game. But even though it’s in the center of town, the Jared Coffin House (a sister property to the White Elephant; 800-248-2405; from $225) is a pretty cool alternative, and you don’t need a car.
From here, you can stroll to the Hub to pick up your morning paper, or pop into Murray’s Toggery Shop for a pair of Nantucket Reds. For the main attraction—the beach—you’ll need a bike. Rent one from Young’s Bicycle Shop.
The better-known beaches, such as Children’s and Jetties, have lifeguards and snack bars that attract families, and the wide white sands and big waves of Madaket, Cisco, and Siasconset draw crowds of bodysurfers and ball-tossers. Locals prefer quieter, out-of-the way stretches like Nobadeer, Quidnet, and Pocomo (great for shelling). To go really offshore, arrange a sailing, deep-sea fishing, or whale-watching trip through the hotel.
Have at least one dinner at Topper’s, the seafood-heavy restaurant at the Wauwinet Inn (there’s a complimentary boat shuttle from Straight Wharf). The red-tide scare has abated, so feel free to dig into the fresh-daily Maine oysters or the lobster and crab cakes. Wash it all down with some Whale’s Tale Pale Ale and a sunset.
2 The Pet-Friendly Adirondacks
If the Point is sold out, try the Lake Placid Lodge.
Actually, you should try the Point (800-255-3530; from $1,250) again: Last-minute cancellations do happen, so check first. But if it’s truly booked, the Lake Placid Lodge (877-523-2700; from $400) is about an hour away, and both properties are incredibly accommodating to pets.
There are about 6 million (no, that’s not a typo) acres of woodland to explore at Lake Placid Lodge, which means Skippy will never chase the same squirrel twice during your rambling hikes. The French-accented meals use organic local ingredients, and dogs get their own menu, with items like chopped filet mignon and salmon fillet.
The Point is outdoors deluxe, which is to be expected from a former Rockefeller retreat. Each of the eleven rooms is unique, there are myriad canoes, sailboats, and windsurfers to take out on Saranac Lake, and after the chef is done preparing your Scottish salmon or Kobe beef, he’ll put together a plate of tasty leftovers and juicy bones for the furry creature lying at your feet.
3 The Outdoorsy Vermont Weekend.
If the Equinox is sold out, try the Woodstock Inn.
Come fall, the picture-book town of Woodstock is overrun with foliage hunters, but on late-summer weekends, it’s a quiet, charming base for gung-ho fresh-air types. The centrally located Woodstock Inn (800-448-7900; from $209) has cozy, elegant rooms, tennis courts, and a Robert Trent Jones Sr.–designed golf course. Sign up for one of Marty Banak’s daylong Wilderness Trails adventures (fly-fishing, canoeing), and the hotel will pack your lunch—Vermont Cheddar cheese, roast-turkey sandwiches, maple-sugar cookies. Reward yourself at dinner with a Falstaffian rack of lamb in puff pastry at the Prince & the Pauper, followed by an amble to Bentleys for a Long Trail Ale. For entertainment, do like the locals: Park yourself on the village green, and watch the fireflies exert themselves.
4 The Cultural Berkshires Weekend.
If the Wheatleigh is sold out, try the Porches Inn.
This time of year, it’s hard not to feel like an outsider in overcrowded Lenox, Massachusetts. So skip the Tanglewood circuit and head to North Adams, about 25 miles away.
Stay at the stylish Porches Inn (413-664-0400; from $220), across the street from Mass MoCA, and take part in its “Whirlwind Arts Escape” package; you’ll get passes to the museum, the Clark Art Institute (Jacques-Louis David’s heroic Bonaparte Crossing the Alps is worth the trip alone), and the excellent contemporary-art collection at the Williams College Museum of Art.
In the evening, dig into the organic popcorn while watching a prime indie film at Images Cinema, or try some of the culinary arts (lamb “lollipops,” vegetable streusel) at Gideon’s (a new North Adams restaurant by Four Seasons alum William Gideon).