Kayaking through the Bermuda Triangle
Travel time: Just under 4 hours by plane.
You’ll love the vibrant colors and the views at Old San Juan’s intimate convent-cum-hotel El Convento; you’ll love the Latino/Caribbean locale even more. (The rum! The rainforest!) But by far the most magical memory you’ll make in Puerto Rico will be kayaking, at night, in the nearby Fajardo Bay, home to a certain type of dinoflagellate that makes the water bioluminescent: Truly, it glows when you touch it. $$
Museum-Hopping in Chicago
Travel time: 2 hours by plane.
Chagall at the Art Institute. T-Rex at the Field Museum. Telescopes at the Adler Planetarium. Sharks at the Shedd Aquarium. The only things standing between you and a complete culture blitz in Chi-town are food and sleep breaks. For the first, go to Matt Fisher’s buzzed-about Bistronomic on the Gold Coast—but also get a flaky-crusted deep-dish pie at the beloved Lou Malnati’s. For the second, we like the übermodern James Hotel, mere steps from Michigan Avenue shopping. And try to visit that other cultural gem, Second City, the improv club where our own Tina Fey got her start. $$
Riverboating Down the Mississippi
Travel time: 3 hours by plane to St. Paul, Minnesota, where the trip begins and ends.
And now for something completely different: Watch the river roll by your stateroom window aboard a Mark-Twain-style steamboat in an Americana-soaked round-trip sojourn that includes a night’s stay in a St. Paul Hilton, three days aboard the steamer American Queen, shore tours, and meals in the grand saloon. $$$
Taking the Air in the Berkshires
Travel time: 5 hours by car.
You think you won’t call the staff by their first names, but within minutes of entering Blantyre—the century-old ivy-covered Tudor manor in Lenox, Massachusetts—you will. And yes, you may even find yourself playing croquet (how dignified of you) on the manicured grounds, and pushing yourself away from the table after canapés on the terrace, and scheduling a rose-scented manicure in your free time, thinking, “So this is what it feels like to be aristocracy.” $$$
Sailing in Cape Cod
Travel time: 1 hour by plane into Boston, followed by a 1.5-hour car ride.
At the idyllic Chatham Bars Inn overlooking Pleasant Bay and the Atlantic Ocean, it’s tempting to simply set up shop with a bucket of littlenecks on your private patio—but you’re on Cape Cod: Time to pop your collar, strap on those Sperrys, and hit the high seas. You’ve got options, depending on whom you’d like to work the mast: Book a private charter on the Inn’s Nantucket Indian wooden sailboat so you can focus on the seals bobbing off the starboard side, or sign up for private instruction and they’ll, er, show you the ropes as captain. $$
Ziplining in Western PA
Travel time: 5 hours by car, or 1 hour by plane into Pittsburgh, then 90 minutes by hotel shuttle.
On the 1,060-foot-long you’d-better-not-have-a-heart-condition Fatbird Flyer Zip Line at rural Fayette County’s luxe Nemacolin Woodland Resort, you’ll soar 300 feet above the earth at about 60 mph—which may not feel fast when you’re driving, but is basically the speed of light when it’s just you and a sling. Accommodations at the property are varied, from the basic rooms in the family-friendly Lodge (from $255) to more luxurious suites and estates (up to $3,000). One zip is $30. $$
Romancing in the Big Easy
Travel time: Just over 2 hours by plane.
With all the debauchery that goes on (and we’re not even talking about Mardi Gras), New Orleans is no place for the kids. So don’t bring ’em. Spend a totally grown-up weekend with a Sazerac in hand, listening to jazz at Snug Harbor and eating oyster loaf from Casamento’s. Stay at the classic, quaint Soniat House, tucked in a quiet residential area of the French Quarter, or—for more modern comfort—the nearby International House. Both are close enough to the city’s star restaurants (Cochon, Emeril’s, etc.) that you won’t need to call a cab … or even put down your drink. $$
Leaf Peeping in Asheville
Travel time: No nonstop flights; 3.5 hours by one-stop flight.
Nestled in the Blue Ridge Mountains, Asheville puts on a fall foliage show that rivals any seen in New England, and offers a wildly diverse range of other delights, from the opulent architecture of the Biltmore Estate to quality microbreweries to the cool indie bookstores and quaint boutiques in town center. Other things we love: The old Woolworth building, with 160 artist booths; the modern Southern fare at Tupelo Honey Café; and Louisa’s Porch, an unfussy B&B with soft beds and a killer breakfast. $
Skiing in Aspen
Travel Time: No nonstop flights; around 4 hours into Denver, then 45 minutes to Aspen.
Sure, we can shop at Prada and Gorsuch on the way to sushi at sexy Matsuhisa, but we’ve also sipped local beers at the chill Aspen Brewing Company clad in hat hair and beat-up snow boots, and felt utterly contented. Aspen—glamorous hot spot/cozy little ski town—is whatever you want it to be (well, it’s first and foremost about the skiing; see aspensnowmass.com for passes, rentals and lessons), and we’ve found that at Limelight Lodge, the mink types mingle easily with skiers in Gap loungewear. $$$
Hiding Out in Maine
Travel time: 1.5 hours by plane into Portland, then 25 minutes by water taxi.
Really looking to get outta Dodge? Consider Chebeague (that’s "shuh-BEEG"), one of the 222 islands off Portland’s coast. It’s quite small—just 3.5 by 1.5 miles—and the sumptuous Greek Revival-style Chebeague Island Inn only offers 21 sunny rooms, with nary a TV or phone in sight. You’ll spend your time walking the rocky coast, kayaking between sun-dappled neighboring islands, and slurping lobster stew at the inn’s restaurant, a favorite of Saveur. $$
Wine-Tasting in Sonoma
Travel time: Roughly 6 hours by plane.
Wine-country tips: 1. Stay at the storybook-perfect Sonoma Farmhouse cottage, which has a kitchen as well as beauçoup adorable restaurants nearby. 2. Whatever else you do (bike to Napa; bop around cosmopolitan Healdsburg), book a private tour via Beau Wine Tours. A chauffeur will cart you to up to five premium wineries —Gloria Ferrer, Ravenswood, Château St. Jean—and you’ll get a gourmet picnic lunch. $$$
Cooking in the Caribbean
Travel time: About 4 hours by plane to St. Martin, then a half-hour ferry ride.
The kitchen might seem like the last place you’d find yourself in sunny Anguilla, but at a resort called (and owned by) CuisinArt, you’d be remiss to skip the entertaining cooking class taught by the so-charming resident French chef. You’ll eat and drink quite well here (grilled lobster night rocks, as does the private wine tasting), but you must still venture off-site to Scilly Cay, a wee island with nothing on it but one tiny beach restaurant with the best barbecued chicken known to man. When you’re not gorging, there’s a cool tour of the hotel’s hydroponic farm, the spa’s unique warm seashell massage, and some of the bluest waters in all the West Indies. $$$
Surfing in the Hamptons
Travel time: A little more than 4 hours by car.
So yes, the main reason to spend three nights here is that you’re going to need time to unwind after the Hamptons traffic. It’s worth it, though: Montauk has the hands-down best surfing on the East Coast; you can grab a board, a wet suit and lessons from Air & Speed Surf Shop. Gurney’s Inn is a sprawling resort with comfy rooms and cottages that sleep eight, should you bring a crew; there’s also the smaller, chicer Sole East, with 61 bright bungalow-style rooms. You should also know about Lobster Roll in nearby Amagansett, where the seafood’s good and the star-spotting, excellent. Gurney’s: $$; Sole East: $
Getting Skinny in Utah
Travel time: 5.5 hours by plane into Las Vegas, then 2 hours by hotel shuttle.
One Philly Mag staffer refers to the place as “Biggest Loser meets Canyon Ranch”: You’re not going to drop three sizes in just a few days at Red Mountain Resort, but the retreat packages are a darn good start. You’ll eat three healthy low-cal meals a day, take an unlimited number of fitness classes, go on guided hikes in the splendid Red Mountains, attend cooking demos, and have access to everyone from nutrition and detox specialists to life coaches. The rooms are nice, too—but nothing compared to the natural beauty around you. $$
Swimming With Stingrays in Grand Cayman
Travel time: almost 4 hours by plane.
There’s no shortage of water sports with which to amuse yourself in the Cayman Islands—the upscale Westin Casuarina Resort & Spa has a ton to choose from on its private beach—but if you’re in the Caymans, you simply must smooch a stingray. Check in with the concierge to arrange a cruise to Stingray City, where you’ll stand waist-deep in water to pet, feed and kiss the friendly rays. (They feel like silk!) Mingle with more sea creatures during dinner at the Wharf, where you’ll feed the thrashing schools of tarpon between courses of conch fritters and Caribbean lobster tail. $$