Frank Sinatra debuted one of the most swinging Palm Springs traditions in the 1950s: Almost every night he was at his Twin Palms Estate (which still stands today), he’d raise a Jack Daniel’s flag at 5 p.m. to alert his friends and neighbors to come over and partake in happy hour around his piano-shaped pool.

 

When I’m in need of a major dose of Vitamin D (or J.D., per Frank’s tradition), I retreat into Palm Springs’ sunny embrace. Steeped in enough swagger and style to outlast the coolest cats in town—just about every big-name celeb has had a brush with Hollywood’s first love—its effortless cool delivers from dawn till dusk. Think of this 48-hour guide as your Sinatra happy-hour flag.

 

Day one

 

9 a.m. Breakfast is a big deal in the desert. While I dream of the huevos rancheros, complimentary smoothie shots, and coffee served in silver carafes at Norma’s in The Parker Palm Springs, I’m also drawn to the shake with dates, vanilla bean gelato, and almond milk at King’s Highway, a former and upstyled Denny’s in the Ace Hotel & Swim Club Palm Springs. And I’d be remiss if I didn’t tell you about Cheeky’s, my third morning must-eat, for the bacon flight alone! Follow your protein fix with the owner’s favorite dish: crispy buttermilk waffles doused in salted butter and syrup. Go early to avoid the line-up.

 

Lemonade Stand at The Parker Palm Springs

 

 

10:30 a.m. Palm Springs is a living and breathing museum for midcentury modern design—it’s home to the country’s largest concentration of the throwback structures and style. This is one of the reasons I’m in love with California’s hottest desert outpost. From Cheeky’s, stroll north along North Palm Canyon Drive into the Uptown Design District to spot iconic furniture finds from famed designers such as Bertoia and Saarinen that dress the city’s midcentury homes. And while you’re in the place that popularized poolside cocktail parties, play the part in a scene-stealing dress or striped seersucker suit from desert-based designer Trina Turk. It’s a shop so legitimately chic, you’re offered a chilled mimosa upon entering.

 

Noon. Check into Korakia Pensione, and if your room is not ready—check-in is technically in the later afternoon—cool off under the shade of an umbrella beside one of two saltwater pools at the Mediterranean-inspired retreat.

 

4 p.m. Replenish your sun-scorched electrolytes at the Lemonade Stand, deep in the citrus grove at The Parker Palm Springs. Sit and sip a muddled lemon bev of your choosing at the chic white marble bar, or under the shade of a tangerine and yellow umbrella. And since you’re on vacation, head a few steps leeward to PSYC (Palm Springs Yacht Club), a nautical-themed spa offering a co-ed dipping pool and boozy pre-treatment shots. I’m a fan of the Motley Mix, a facial-massage-manicure package, which I’d chase with vodka (sorry Frank).

 

7 p.m. Since you’re already at The Parker, saddle up to the six-seat Mini Bar for a sip of Jack Daniel’s on the rocks. It’s tradition (albeit a little late)!

Viewfinder Tip: While parts of Palm Springs are walkable, a car will allow you to cover the most ground during your 48-hour itinerary.

 

8:30 p.m. Satisfy your stomach at Birba, an alfresco pizza and pasta place warmed by the wood-burning pizza oven and a bevy of outdoor fireplaces. Birba is my first dinner stop every single time I lollygag in Palm Springs. Don’t miss it.

 

Day two

 

9 a.m. Korakia Pensione includes breakfast in one of the most gorgeous settings in the Coachella Valley: a spot next to a fountain under the shade of orange trees. Bite into a rotating menu of dishes like rustic potatoes paired with eggs and multigrain toast.

 

10:30 a.m. Since Palm Springs and modernism mingle in the same circles, check out some of the homes that have helped to make the city famous. Call Robert Imber at Palm Springs Modern Tours or stop by the Palm Springs Visitors Center for a US$5 map of Modern Palm Springs. Both the DIY and hosted tours are excellent; choose one based on how much time you want to spend drooling over design.

 

Hiking in Palm Springs

 

 

1 p.m. The San Jacinto Mountains, visible from nearly every sun-scorched vantage point, beg to be conquered. Rev your heartbeat and score a killer view of the Coachella Valley hiking one of the many trails that start along the edge of town. Talk to your hotel concierge for a list of nearby trailheads. And don’t forget lots of water—after all, it is the desert!

 

3 p.m. You’re in Palm Springs, so spending time by your hotel pool is not only encouraged, but expected.

 

8 p.m. Toast your last night of desert decadence at one of Palm Springs’ most iconic addresses, the ever-hip Purple Palm Restaurant and Bar. Named in a nod to the hotel’s original owner—a mob boss and member of the Purple Gang—the elegant eatery is perched next to the Colony Palms Hotel pool, where Frank Sinatra once sat (when he wasn’t raising a flag and a glass at his Twin Palms Estate).

 

What’s on your Palm Springs must-do itinerary?