Esperanza Resort, Cabo San Lucas
La Playa Hotel, Carmel
The Hyde Bellagio, Las Vegas
Picosa Ranch, San Antonio
Someday I want to...Private-jet to St. Moritz.
But for now I'll...Fly (commercial) to Mammoth Lakes.
For a close (OK, close-ish) approximation of the Swiss Alps—not to mention a speedier alternative to the usual slo-mo slog to Tahoe—hop a 60-minute United Airlines flight from SFO to Mammoth, starting this ski season. Join a mostly SoCal crowd for the one-mountain ski town’s heaps of powder, swank village, and year-old hutch of elegant mountain condos called Auberge Residences at Mammoth. (Yes, that Auberge, of Napa Valley fame.) The resort’s staffers are omnipresent: Each morning they’ll set out your gear on the hotel’s private pedestrian bridge to the gondola, and each evening they’ll unbuckle your boots, prep your skis for the following day, and let you adjourn to a private screening room to catch a flick, or to the roof for a nice steamy hot tub. From $325. — Lisa Trottier
Someday I want to...Quit my job and become a hotshot winemaker.
But for now I'll...Live like one—for a stint—in Napa.
The Farmhouse at Poetry Vineyard, smack in the middle of Cliff Lede’s property in Napa’s Stag’s Leap District and formerly inhabited by the winemaker himself, is now rentable. Sure, it’ll run you $8,000 to $12,000 a month, but consider the spread: three spacious bedrooms, a heated pool, a hot tub, and a wood-burning fireplace, plus decks, lawns, and all the little touches of the Poetry Inn itself (candles, L’Occitane products, fluffy robes, etc.). Though you’re a stone’s throw from four Michelin-starred restaurants, you can also order in from Bistro Jeanty—or better yet, bring in a chef and a winemaker (Cindy Pawlcyn and Lede’s in-house vintner, perhaps) to cook up a wine-pairing feast on your back patio. — Rachel Levin
Someday I want to...Make life one big Abu Dhabi pool party.
But for now I'll...Zip down to always-sunny Palm Springs.
Like the Middle Eastern desert oasis, Palm Springs is the land of a zillion swimming pools, 70-degree winters, and chiseled cabana boys ferrying freshsqueezed margaritas to your lounge chair. The new confetti-colored Saguaro Palm Springs heats up on weekends, when DJs draw Angelenos in all their retro high-waisted-bikini glory. Impromptu dance parties are de rigueur at Viceroy Palm Springs and the Ace, but for a break from the dubstep, the newly remodeled Del Marcos Hotel has a Rat Pack vibe, along with free bikes and breakfast. No bar, but also no shrieking kids (adults only). Saguaro, from $159; Del Marcos, from $139. — Samantha Schoech
Someday I want to...Slip my screenplay to Harvey or Robert at Sundance.
But for now I'll...Opt for Clint in Carmel.
If you want to sprinkle some Hollywood glamour into your off time, you could compete with Weinstein and Redford plum rooms, hot tables, and fresh tracks in Park City. Or you could choose a less-resistant path and hang with Central Coast–er Eastwood (and his empty chair perhaps?) at the Carmel Art and Film Festival (Oct. 10–14). Stay at La Playa Hotel, newly reopened after a $3.5 million facelift, which maintained the resort’s beachy feel and preserved its century-history. Catch a free ride into town for like About Face: The Supermodels, Then and Now. If Eastwood’s a no-show, you settle for L.A. street artist Mr. Brainwash, star of 2010’s Exit Through the Gift Shop. La Playa Hotel from $249; Film Festival passes from $50. — Kate Conger
Someday I want to...Cycle around Provence with my French lover.
But for now I'll...Bike through wine country with my future lover.
Backroads is hosting its first-ever Singles-Solos Bikefest in wine country on September 30, covering five nights and six days, with 100 swinging, cycling, cab-sipping singles participating. The 317-mile route (don’t worry: You don’t have to ride it all and can calibrate your daily mileage to your ability) starts in Yountville and winds through Healdsburg and on out to Bodega Bay and Olema before ending back in San Francisco. Along the way you’ll indulge in picnic lunches and farm-to-table suppers, bonfires, dancing, camping, and sleeping (maybe together) under the stars. You know, like the Bay Area version of Bachelor Pad, but without the drama. $2,198, inaugural trip Sept. 30–Oct. 5, with more dates in 2013. — Jenna A. Scatena
Someday I want to...Gallop like an Argentinian gaucho.
But for now I'll...Rope steers like a Montana cowhand.
Your plaid, western-style shirt is fine for Valencia Street, but it’ll look even more appropriate in Whitefish, Montana, newly reachable via affordable nonstop flights (from as low as $80) on Allegiant Airways. In the fall, leaves turn yellow, Oktoberfest takes over the town, and the summer tourists are gone, leaving Glacier National Park for just you and the grizzlies. Set up camp at Bar W Guest Ranch, which sits on a trout-filled pond and pairs resident cowboys with city slickers to transform the latter into cowherdin’, rope-whippin’, horse-ridin’ wranglers in just three (or six) days. If you’re hooked by the time of the ”competitive” rodeo at the stay’s end, you can sign up for a six-day cattle drive in June. But beware: You’ll get down and dirty, and maybe even, uh, castrate some steers. Otherwise, with wine tasting, hot tubbing, mountain BBQs that go far beyond baked beans, and a field full of new glamping tents, Bar W is a little more luxe than Lonesome Dove. All-inclusive, double-occupancy tents $1,455 for six nights; $728 for three nights. — JAS
Someday I want to...Buy an oceanfront hacienda in Cabo.
But for now I'll...Shell out just $88 a night in Todos Santos.
A private Cabo estate this is not. But just an hour from the spendy, trendy resort town’s all-inclusive 600-room hotels is Todos Santos’s intimate new Hotel Casa Tota. A hip under-the-radar spot in the tiny and still refreshingly undeveloped beach town, located a short walk from both sand and taco stands, the 15-room hotel has ceiling fans and AC, as well as platform beds and plasma TVs. The adjoining restaurant and cantina, La Santeña, has quickly become one of the best in Todos Santos, using herbs from the rooftop garden and all local ingredients for everything from the espresso to the handmade tortillas to the queso made by the bartender’s father. There’s alfresco morning yoga, a ”hammock lounge,” a poolside cerveza ”honor bar,” a knowledgeable staff, and free Wi-Fi if, for some reason, you want it. From $88. — Jess Chamberlain
Someday I want to...Do Vegas like a Bond villain.
But for now I'll...Book a luxe suite and pretend I'm one.
For most of us, Vegas trips are more Hangover than Diamonds Are Forever. But just for once, wouldn’t it be nice to experience the suave side of Sin City? Behold, the dream Vegas itinerary: Descend from your penthouse suite at Aria Resort (From $875), where your limo awaits (a red-carpet perk afforded all Aria suite guests) to whisk you away for $850 bottles of Dom at Hyde Lounge, a newly opened redoubt at the nearby Hyde Bellagio. If you want to be treated like a true VIP, shell out a little extra (like, oh, $250,000) for the right to press a button inside a sleek black briefcase—delivered by a waiter playing the henchman Mr. Wint to your evil Ernst Stavro Blofeld—and you (yes, you) can bring the famed Bellagio fountains to life. Another $500 buys you a limo and 18 holes at Shadow Creek, a lush green golf oasis, where you might catch a glimpse of Michael Jordan in the clubhouse’s locker room. Sign up for a racing lesson in a $300,000 Ferrari 430 Scuderia with Exotics Racing, a gleaming gearhead operation with a fleet of supercars and a freshly minted 1.4-mile racetrack. When you realize you can’t live on adrenaline alone, repair to the Four Seasons for a $2,000-a-head private cooking class with Mr. Palmer of Charlie Palmer Steak. Having racked up quite a bill, it’s time to take the house down at the Talon Club, a new high-stakes gaming room at the Cosmopolitan Hotel that resembles a speakeasy for the Sun King. — Josh Sens
Someday I want to...Disappear into an artfully rugged inn on the coast of Maine.
But for now I'll...Ditto. But in South Lake Tahoe.
Don’t be distracted by the high-rise casinos and the all-you-can-eat buffets; there are legitimate signs of hipness emerging around Tahoe’s south shore. Exhibit A: Basecamp, a 50-room motor-court motel just redone into a squat for the design-savvy outdoorsperson, with lithographed antler art, orange loft beds, retro camping lanterns in lieu of lamps, a rooftop hot tub, and communal dinners where guests share adrenaline-soaked tales over oozing pots of raclette or fondue. A two-block walk from Heavenly’s gondola, Basecamp is ideal for skiers who’ve graduated from dumpy hostels but still want to save their money for the slopes. Come before the ski season starts and you’ll get rock-bottom rates and first dibs on the hotel’s cruiser bikes, which you can ride along the network of paths to, say, the revamped grassy shoreline at Lakeview Commons for a real I Heart Tahoe moment. From $99 before Dec. 15. — LT
Someday I want to...Perfect my tittibhasanas with a yoga guru in India.
But for now I'll...Make that sun salutations in San Luis Obispo.
The scenic drive through the Central Coast’s Santa Margarita Valley sure beats a cramped flight to Goa. Set on a 45-acre historic ranch with endless views of the golden hills is Sagrada Wellness, a year-old yoga retreat center for beginners and contortionists alike. With a spring-fed pond and trails leading to shaded Adirondack chairs, fresh veggiecentric food, and just four guest cabins (with two more rooms, plus a new six-room dorm, on the way), life here falls into an easy rhythm. Wake with the sun for coffee and a meditative walk through the woods, followed by a simple breakfast of, say, steel-cut oats prepared by architect-owner Scott Currie, who designed and runs the place along with his acupuncturist wife, Eva Inglizian. Meditative and vinyasa-style yoga classes are offered twice daily (10 a.m. and 4 p.m.). And in between, you’re free to hike, splash around in the aboveground pool, or head a few miles down the road to sip pinot noir at Ancient Peaks Winery—after all, this is the southern Paso Robles appellation. Due to high demand (there were 25 people on a recent waiting list) Sagrada is closed for expansion this fall, but it will reopen in December to flaunt its new 800-square-foot yoga studio with a cork floor, 20-foot ceilings, and three sliding glass doors opening onto the oak trees beyond. From $795 for three nights; retreats limited to 15 people. — Michelle Hamilton
Someday I want to...Feel like I live in a Wes Anderson movie.
But for now I'll...Sleep in a tree house in Washington state.
In a tiny, woodsy, Moonrise Kingdom–esque town 20 miles from Seattle is a magical place called Treehouse Point, where seven hand-built works of Pete Nelson’s inhabitable art are now scattered around four acres along the Raging River. And we’re not talking flimsy, splintery platforms propped up by a wannabe handyman dad, but actual tree houses—built into red cedar and Sitka spruce trees. Most of the midair cabins have glass windows, leather reading chairs, hand-stitched quilts, and vases of fresh flowers—and each is as sturdy as any city apartment, but prettier. Some are accessed by swinging footbridges, others by stepladders, and all offer a unique quiet. You know, the kind only trees get to experience. But now, humans with a couple hundred bucks can also. Bring friends, a guitar, and, now that you’re all grown up, beer. There are nearby hiking trails, a river flowing with salmon, ready-to-light fire pits, and oversize hammocks strung 20 feet high. The main lodge has a master suite and a massage studio, and in the morning you get to enjoy berry scones right out of the oven. From $200. — RL
Someday I want to...Hike the entire 2,650-mile Pacific Crest Trail from Mexico to Canada.
But for now I'll...Whoa, there. See how I handle a section of the Sierra first.
Before you set off on a multimonth trail into the unknown, try hiking with someone who knows what the heck they’re doing. Tahoe Adventure Co. just launched custom backpacking trips along the northern Tahoe Sierra crest of the PCT. Two- to eight-day expeditions are available for eight people max, starting from Squaw Valley and heading due north to Truckee if you like. This is the first commercial guided trip in the region, and one of the only sections of the famed trail that even offers guided trips. Along the way you’ll climb Castle Peak (with its dramatic volcanic summit), pass dozens of inviting lakes, and watch golden leaves fall from the trees. On a clear day, views stretch all the way to Mt. Diablo. Fall is actually the perfect time to go: Summer crowds are gone, days are still warm, and evenings are usually above freezing. “But remember,” warns owner Kevin Hickey, “this is the mountains”—meaning it could start hailing at any moment. From $160 per day.— JS
Someday I want to...Relive my wedding day.
But for now I'll...Re-create some of the magic at Holman Ranch.
Forget the awkward toasts and forced mingling. Here it’s just you, your soul mate, and—if you choose—a few close friends frolicking around one of Northern California’s prettiest, most popular wedding venues. The newly renovated Holman Ranch, a 1928 stone hacienda situated high on a quiet grassy hilltop in Carmel Valley and surrounded by views of the Santa Lucia Highlands, now has 10 simple guestrooms available for rent. Ride horses along trails, try archery in the fields, or even bring in a falconer, if you’re so inclined. Otherwise, you’re free to lounge by the pool (which dates back to the 1940s), sip Holman’s new estate-grown sauvignon blanc and pinot noir, barbecue (or cook in the gourmet kitchen), and retire to the game room for billiards. Or, play horseshoes, roast s’mores by the fire pit, bundle up beneath the stars, and kick back to a chorus of croaking frogs as you laugh about how much easier this ”wedding” is than the first one. From $250. — RL
Someday I want to...Heli-ski through endless Alaska powder.
But for now I'll...Same adrenaline rush, but in the Sierras.
After nearly 20 years as a backcountry guide in Alaska’s Chugach Mountains, Dave Rintala realized the town of Valdez was getting too overrun: ”With 17 heli operations and more opening all the time, the days of first descents there are over,” he says. So he decided to bring helicopter skiing to the Sierras. Rintala’s two-year-old company, Pacific Crest Heli-Guides, whisks advanced skiers and snowboarders into vast, remote tracts of some of the freshest powder in the West. Get plopped into the powder with just three other choppermates, strap on your fat skis and backcountry safety equipment (provided), and then start making laps. You ski down, then are coptered back up, as many times as your legs can handle. Lunch is typically a hearty deli spread enjoyed in the snow. After a day of laying down tracks on Tahoe’s secret couloirs and chutes, rest your weary body at Truckee’s Cedar House Sport Hotel, where Pacific Crest will pick you up the next day, to do it all over again. $899. — KC
Someday I want to...Throw the mother of all bachelor parties (just not in Vegas).
But for now I'll...Shuttle my bros to a lodge in Texas.
Texas? Yup. The Lone Star State may not have blackjack, but it does have space: wild, wide open, and, in the case of 2,500-acre Picosa Ranch, downright luxurious. This former hunting lodge has recently softened into a five-star (but still manly) experience: There’s skeet shooting, fishing, and hog and turkey hunting. Also horseback—or Hummer H2—riding. Exotic animals, like oryx and zebra, roam the property too— but, sorry, you can’t shoot them. There’s a 14-person staff ready to, say, mix martinis in the billiards room, grill up steaks by the heated pool, or serve you and your posse a complete five-course customized dinner with wine pairings, and maybe whiskey and apple pie for dessert. Should you want to venture off the sprawling grounds for some insane reason, a Bentley is at your beck and call. There’s a private airstrip too—plane not provided. From $7,500 per night for 18 people; from $30,000 for 26 people; can accommodate up to 42 people, for an additional nightly charge. — Connie Dufner
And in case you still have reservations about making those reservations, the Excuse Buster:
NO: "I get all the Portland I need from Portlandia."
YES: "Why not? I'll put a bird on it."
Portland is San Francisco’s scrappier, kookier, thriftier kid sister (or to use a Portlandism, our spirit animal). Take advantage of the new SFO–PDX flights on Virgin, and stay at the new McMenamins’ Crystal Hotel & Ballroom (from $85), order beef rib eye at hotspot Ox, shop free of sales tax, and maybe even do some house hunting—a three-bedroom hovers around $350,000. Sigh.
NO: "I’d splurge for the French Laundry, but I can’t stand the reservation system."
YES: "Thomas Keller is my BFF."
Plunk down a cool $3,900 and Sonoma inn and culinary school Ramekins will lock in VIP access to Napa’s most rarefied private dining room. As part of its Culinary Retreats program, the inn also sets up winemaker-led tastings, oyster lunches at Hog Island, and classes with chef Mary Karlin.
NO: "Mexico, si. Mexico for a thousand bucks a night, no lo comprendo."
YES: "These fish tacos taste like freedom."
Cabo’s exclusive cliffside Esperanza Resort, fresh off hosting Barack and Hillary for the G20 Summit in June, is celebrating its 10th anniversary by offering three-day stays for $525 to $675 a night through mid-December, with a fourth night free. But note: By the holidays, the sky-high rates return.