San Francisco

If hurtling across an iconic, rust-colored suspension bridge on two wheels, dodging selfie-stick-wielding tourists while being assaulted by unpredictable gusts of wind sounds like your cup of artisanal kombucha, then biking across the Golden Gate Bridge is for you. Completed in 1937 during America's great depression-a dazzlingly optimistic feat of engineering-this Art Deco masterpiece was initially dubbed "impossible" to build. Today, pedaling its length guarantees surreal views of San Francisco's skyline glowing smugly in the distance, dramatic cliffs plunging into Pacific waters, and perhaps even a fog bank dense enough to swallow Hitchcock characters. Go early-seriously, early-before 9 am if you'd rather not be locked in mortal combat with crowds, and layer up as Bay weather can swing from postcard-perfect to frostbite-inducing quicker than you can say "tech IPO." Renting bikes downtown is easy, just budget around $30-40 for the day, helmet included (yes, wear the helmet-your Instagram won't mind). Allow yourself a leisurely couple of hours to coast into quaint, artsy Sausalito, where an overpriced but undeniably delicious seafood taco awaits you. Then, smugly ferry back to San Francisco, knowing you've conquered an architectural wonder, witnessed history, and earned bragging rights that'll last longer than your bike-seat soreness-and trust me, you'll have a story worth spinning at dinner parties for years.

Driving down Lombard Street is the vehicular equivalent of trying to thread spaghetti through a needle while perched comfortably atop an inclined treadmill-absurd, comical, and oddly thrilling. Located in San Francisco's prim Russian Hill neighborhood, this picturesque jumble of eight hairpin turns-often dubbed the "crookedest street in the world"-began life in the 1920s as an eccentric but practical solution to the area's steepness, sparing early Model T brakes (and passengers) from certain doom. Today, it's less about function than the sheer goofy joy of saying you've navigated a thoroughfare that looks like it was drawn in crayon by a sugar-crazed child. To avoid gridlock-induced despair, plan your winding pilgrimage early in the morning or just after sunset, when the Instagrammers are still fumbling for their coffee or moving on to craft cocktails elsewhere. Budget-wise, this slow-motion amusement park ride is technically free, though spare change for parking meters and patience-inducing caffeine are recommended. Bring your widest-angle lens, a healthy disregard for fuel efficiency, and a mild sense of adventure. Sure, driving Lombard Street won't change your life-but trust me, the absurd bragging rights at dinner parties alone are worth the dizzying inconvenience.

San Francisco by night is a strange and wonderful beast-half glittering postcard, half neon-lit noir, sprinkled with the occasional waft of sourdough and questionable life choices. Trust me, a guided nighttime romp through this mad cityscape is less tour and more existential odyssey, weaving you through neon-lit signs, Chinatown's hidden alleys, and the mysterious fog whispering secrets that probably involve Gold Rush ghosts and Beat poets arguing in eternity. Book your spot a week or two ahead, cough up roughly fifty bucks per person, and hop onto this nocturnal exploration around 8 p.m.-prime time for mischievous street artists, jazz enthusiasts, and tired tech bros staring deeply into overpriced cocktails. Do yourself a favor and layer up (fog in July? Welcome to San Francisco) and carry a little cash for late-night dim sum or street tacos-because culinary courage peaks under the neon glow. No matter how uneasy you feel about guided tours-sure, they're a little touristy, but they're also hilariously enlightening-this adventure is worth the price of admission, even if just to say you've seen a skateboarder narrowly avoid a cable car while a saxophonist serenaded them both beneath the twinkling lights of the Bay Bridge.