As November’s gothic gloom segues into interminable Portland Gray, the plotting begins. We crack open atlases, plot equatorial flight paths, and Google “dry heat.” Whither warmth, we ask?

Sure, there’s Baja and Kauai. But we say follow the pros to Palm Springs, a California oasis that’s lured snowbirds for a century-plus. Once a desert-climate retreat for wheezing Edwardians and captains of industry, Palm Springs keeps evolving: into a playground for golden-era Hollywood wealth, then for midcentury aesthetes, and, increasingly, for retirees. Even now, a certain Bob Hope-y aura lingers over its vast golf courses, exacting modernist manses, and boutiques replete with glam old-Cali gowns.

But this mini-city just removed from the LA megaplex—and only about a 2½-hour direct flight from PDX—has lately pulled off its most extreme reinvention yet, one focused on art, design, commercial ambition, and social progressiveness. Its booming cultural scene prominently features the Coachella Valley Music and Arts Festival (April 12–21), à la Instagram and mythic Beyoncé sets. The city’s architectural heritage anchors an internationally significant Modernism Week. And in politics, Palm Springs recently put a thumb in the eye of various dark forces with its election of an all-LGBTQ city council.

But for one of the most compelling reasons to wing south, take a literal step back from human accomplishments to witness the off-world landscape of the San Jacinto Mountains, framing a place where badlands grit and urbane glamour both bake in the sun. Need even more motivation? Read on. —Zach Dundas

The art world is all here.

Modernism Week—the city’s signature annual two-week fantasia of midcentury chic, tours, and parties (Feb 14–24)—lures thousands of sun-splashed design and architecture geeks. The concurrent Art Palm Springs (Feb 15–17) is an elite cluster of talks, gallery shows, and other events. Year-round, the ambitious Palm Springs Art Museum shows metro-caliber visual artists, with two winter exhibits to spark Oregonian pride: Unsettled, a high-concept crosscut of art from across the “Greater West” features Portland’s Wendy Red Star (plus, y’know, Georgia O’Keeffe), while Some of My Favorite Things samples the glass art collection of Portland culture patrons Harold and Arlene Schnitzer. —ZD

So many dreamy hotel pools ...

In Palm Springs, you’ve got dusty desert-rat motels, charming mom-and-pop outfits, and condos ranging from skeez to chic. But the classic Portland lodging choice is the nine-year-old Ace Hotel & Swim Club, a now-famed reboot of an old HoJo that’s basically a mini-Rose City embassy. A few blocks away, Sparrows Lodge offers a chill, vintage-rustic counterpoint. On the still higher end, consider the Riviera’s neo-Rat Pack vibe and vast double pools (“Soleil” and “Chiki”). —ZD

The food comes with a view.

Mornings start in the bustling courtyard of local roastery Koffi North, where locals knock back iced lattes under the beatific gaze of Mount San Jacinto. Extend the day’s delights with all-day breakfast on Norma’s sunlit terrace at the ebulliently outfitted Parker Palm Springs. Come starlight, doll up for Birba, where pizzas pair up with bright salads and bresaola on a buzzy, firelit patio filled with fashionistas. —Fiona McCann

There’s a tram from sand to snow.

Surrounded by the San Jacinto range and the parched beauty of the Coachella Valley, Palm Springs is a killer outdoors destination. Indian Canyons—just minutes from town on the Agua Caliente Band of the Cahuilla Reservation—offers miles of hikes to fierce vistas and surreally lush oases. (Also on Agua Caliente land, Tahquittz Canyon threads up to a towering waterfall.) But for a truly mind-boggling close-in adventure, take the rocket-like Palm Springs Tramway up 8,500 feet to a network of friendly alpine trails accessed via “Mountain Station.” Snow in the desert? It’s here. —ZD

The vintage shopping is on-brand.

From Valentino to Chanel, there’s nothing like The Fine Art of Design’s racks of perfectly preserved duds. Equally colorful (but less fancy) scores abound at the year-round College of the Desert (COD) Street Fair—nearly 300 vendors peddling watercolors to patio furniture. Or day trip to Cabazon (ogle the giant roadside dinos from Pee-wee’s Big Adventure on the way) to explore the Desert Hills Premium Outlets’ endless racks of discount Armani, Gucci, and more. —Eden Dawn

Even the dive bars are de rigueur.

In Palm Springs, weird times in dive bars are the lime wedge in life’s margarita. Find them when you belly up to Billy Reed’s 43-year-old stained-glass-beaming bar, with a tumbler of gin and a slice of fresh pie. Or try the tiny Bootlegger Tiki Bar and sip a glass of Pearl of Wisdom—a lethal house mix with pineapple, cold brew, falernum, and rum—in the company of many wall-mounted sirens. —ED

You can play sheriff in Pioneertown.

“Hoof-n-foot only” reads the hand-painted sign signaling the pathway (more like dirtway) into Pioneertown—a ’40s-era living Western movie set 32 miles from Palm Springs. Roy Rogers was an original investor, and scores of movies and TV shows (Annie Oakley, The Gene Autry Show) were filmed here. Today, it’s a street-long tourist destination, free to the public and replete with costumed locals. Mosey over to Pappy & Harriet’s—a legendary barbecue and honky-tonk joint, for rib eyes and whiskey. —FM 

Joshua Tree is a prickly, paradisiacal refuge.

Twelve miles south of the north entrance to Joshua Tree National Park, the boardwalk at Cholla Cactus Garden offers safe passage through spiny, winter-blooming succulents: desert lavender, hedgehog cactus, the disingenuously named teddybear cholla. Elsewhere in the nearly 800,000-acre preserve, find massive rocks and Joshua Tree’s eponymous, elegantly gnarled yuccas along the three-mile 49 Palms Oasis Trail. Fair warning; there’s no glistening pool under those fronds—instead, make your post-hike watering hole the poolside bar at the 29 Palms Inn, a “gateway to Joshua Tree” some 53 miles from Palm Springs. —RD

November direct round-trip flights from PDX to PSP start around $200 on Alaska.

Top: the courtyard pool at Saguaro. You can detour for tequila shots to El Jefe, the hotel’s dim, timber-paneled bar. (Courtesy Mark Brooke)