14 Movie-Inspired Summer Flings

If we learned anything from 500 Days of Summer, it was that not all summer romances end on a happy note. Up your chance of getting the girl by taking her on a string of 500 Days-inspired La La Land dates: vintage record shopping at Echo Park’s Origami Vinyl, bench sharing at the pretty lily pad–strewn Echo Park Lake, and karaoke at Café Brass Monkey. We can’t promise your love will make it to autumn, but we can guarantee an unforgettable stay at Koreatown’s Line Hotel, a hip-kid playhouse with concrete walls, vintage-inspired paisley rugs and floor-to-ceiling windows. Swing by the hotel’s Poketo outpost to browse the locally designed jewelry, or pedal around town on two of the hotel’s free Linus bikes. But whatever you do, just don’t try to put a label on it.

Have a fling (or three!) Mamma Mia!-style on Patmos Island, Greece. With no airport, and reachable exclusively by water (ferries set sail from Skala just three times a week), the small, hilly island practically invites a secret tryst. The site of your moonlight romps and disco dances is the Petra Hotel & Suites, an 11-room boutique with an idyllic clifftop perch, crystalline water views, and a stone-covered bar and lounge with a rugged, tucked-away appeal. If you’re seeking privacy, stroll the area’s shingly beaches and explore its secluded coves, before sampling Greek tapas on the veranda high above the sea at Tzivaeri Taverna. Chasing the sunrise? Many a dancing queen have boogied down with their kings to sultry live Greek music at Art Café, the only rooftop bar in Patmos.

If your trade is jewelry theft, your chariot a metallic 1953 Sunbeam Alpine Mk.1 and your home a vineyard-flanked mansion on the French Riviera, your summer fling game requires no improvement. But if you’re not swagging out like Cary Grant in Hitchcock’s To Catch a Thief, take a few tips from us. Stay at the 21-room Tiara Yaktsa Hotel, a Moroccan villa-inspired sleep complete with a sexy infinity pool, an elegant French restaurant and romantic guestrooms with balconies that overlook the Mediterranean. Rent a set of convertible vintage wheels and zip around town to the nearby Côtes de Provence vineyards (a wine tasting at Domaine Croix-Rousse is a must), or to Cours Saleya, the famous open-air flower market in Nice. No masquerade ball to crash? No worries. You can get the gold standard of nightlife at the exclusive Le Bâoli Beach nightclub in Cannes. Uber helicopters sold separately.

Caught in a love triangle? Need to get the guy fast? Take a page from My Best Friend’s Wedding and bring your competition to karaoke. Chicago’s songbirds congregate at Alice’s Lounge, a neighborhood joint known for its strong drinks and critical crowd. (Hey, it’s not your problem she can’t hit the high notes.) But petty sabotage is bound to get you bent out of shape, or, at the very least, in need of a stiff drink — lucky for you, the Virgin Hotel Chicago has all the creature comforts you’ll need to stay in tiptop form, including a spa, fitness center, coffee shop and guestroom mini fridges stocked with Veuve Clicquot. Tell him how you feel (before the moment passes!) at the romantic Spiaggia restaurant on Chicago’s Magnificent Mile, which has seen more than 1,300 engagements in its day. You can thank us later.

Sure, Blue Crush is no Citizen Kane, but it did teach wannabe millennial surfer girls everywhere how to find love on Oahu’s North Shore. (In a nutshell: complete high school, rock some hemp jewelry and say "yes" when a hot NFL quarterback requests surf lessons.) Prove to him you’re no mainlander by upgrading his drab digs. The Kahala Hotel & Resort on the eastern side of Oahu’s Diamond Head crater is renowned for its lush spa, beach cabanas, water sports and on-point restaurants. Treat your crush to a burger and a root beer float at Honolulu’s Rainbow Drive-In, a favorite of President Obama’s (and Guy Fieri’s), or show him how the locals do at Arnold’s Beach Bar & Grill, a laid-back grass-roofed spot with enough hot surfer dudes to get him more than a little concerned.

Hey girl, we hear the next best thing to Ryan Gosling building you a home with his bare hands is a stay at the cottages of South Carolina’s Inn at Palmetto Bluff. Sure, it’s no white house with blue shutters, but hey, take it slow and you too may find a blue-eyed bearded heartthrob of your own. Plan your future together on the hotel’s shabby-chic veranda, or paddleboat down the May River under a lush canopy of live oaks and Spanish moss. Dark clouds ahead? Reenact your favorite movie moment (cue: "It wasn’t over. It still isn’t over!”) on the dock of the bay, then seek shelter in your cozy forest cottage. With pine floors, Italian bed linens, deep soaking tubs and stone fireplaces, the rooms are so ridiculously romantic that you won’t need to convince her to stay.

From Tinder hookups to Match.com dates, serendipity seldom plays a role in modern-day versions of boy-meets-girl. Find your Before Sunrise–inspired chance encounter on Vienna’s historic streets, which are filled with imperial palaces, stately public squares and lavish opera houses. Stay up all night pondering life’s biggest questions at The Café Landtmann, Sigmund Freud’s favorite living room–style coffee house, then crash at Hotel Das Triest in downtown Vienna, where the guestrooms are done up in local artworks and have their own private gardens. Before going your separate ways, take your sweetheart to the historic Wiener Riesenrad Ferris wheel and vow to meet up in six months time while suspended high above the Danube.

New York City’s answer to a tall, dark, handsome stranger? The paranoid, death-obsessed Jewish comedian, Alvy Singer. Whether freaking out over his sex life or schooling strangers in critical theory, Annie Hall’s leading man had the hot mess thing down eons before the cool kids. Meet your New York neurotic while standing in line for a highbrow art film at Angelika Film Center, or working on his tennis serve at the Wall Street Racquet Club. Take him uptown to your glamorous digs at the Carlyle Hotel, where every A-lister from Mick Jagger to George Clooney to Kate Middleton have stayed, then skip over to Central Park to share a bench and poke fun at the passersby. Fancy meeting Alvy Singer’s real life stand-in? Make it back to the hotel in time for Woody Allen’s jazz set at the atmospheric Café Carlyle, where the filmmaker and his band take the stage every Monday night.

This summer, sneak around upstate New York with someone your parents don’t approve of. Originally built as an upscale campground, the Whiteface Lodge in Lake Placid has all the retro-inspired amenities you’ll need to live out your Dirty Dancing fantasies, including an ice cream parlor, a movie theater and a bowling alley. Once you meet your man with his shirt off (à la Patrick Swayze) at the outdoor pool or hot tub, take him on a hike through the Adirondack Park to the village of Lake Placid. There you can jam out to jukebox favorites at Bowlwinkles Entertainment before hitting the town’s public beach. Or if you’re seeking something quieter, head to Chapel Pond, at the base of Rocky Peak Ridge. The water is calm, the shores are crowd-free, and there’s plenty of open space to practice your moves. After all, nobody puts Baby in a corner.

Summer loving, had you a blast. Summer loving, happened so fast. Now it’s September and your leather jacket–clad bad boy has all but forgotten about those sultry summer nights spent down in the sand. Skip class with the girls and make a plan to win him back over shakes and burgers at John’s, an uptown retro-themed diner serving all-American comfort food around the clock. Afterward, go shopping for that night’s party dress at Route 66 West, a vintage store known for its colorful retro baubles and flirty/sexy dresses. Come evening, slip on your dancing shoes and throw the party of the year at the Ace Hotel and Swim Club’s rock and roll–inspired pool. The drinks (alcoholic snow cones, naturally) are served from a retro ice cream truck, and the DJs spin vinyl into the early hours of the morning. A+ for the new girl at school.

Summer jobs suck, from the pitiful pay to the starchy uniforms with unflattering cuts. Take a cue from Adventureland and make the most of your minimum wage gig by finding a summer crush. Noisy pinball machines and Whac-A-Mole are great for preteens, but not so great for a grown man trying to impress a lady. Show her you did your research and take her on a date so epic it would turn even K-Stew’s frown upside down: pancakes and vanilla shakes at Square Café, lawn bowling in Frick Park, beer and pierogi pizza in a church turned brewery, and then a free movie under the stars at Pittsburgh’s most popular make-out point, West End Overlook. You’ll have had so much fun you’ll forget you just blew a whole paycheck.

How is a small town girl to pass those listless summer afternoons? Follow the lead of My Summer of Love and take to exploring the countryside. Pack a picnic and roam Yorkshire’s heathery moorlands and charming hamlets on horseback before cooling off with your girl in Lake Gormire, a tucked-away swimming spot with crystal clear waters perfect for skinny-dipping. After that, stop by the Yorkshire Lavender Gardens to kiss beneath the fragrant purple meadows, or go for a scooter ride to the gorgeous beach town of Scarborough. It may only be a of couple months’ worth of love, but with adventures like these, you’ll never forget that perfect summer.

With grand piazzas, towering basilicas and scores of lovers spilling onto winding cobblestone streets, it’s no wonder Rome serves as the ultimate backdrop for a classic summer fling. Make the most of the time you have together by embarking on a whirlwind Roman Holiday–inspired romance. She’ll hold you tight as you maneuver a cherry-red Vespa through the city’s crowded streets to the Colosseum, then down to the church of Santa Maria in Cosmedin, where you can stick your hands into the iconic Mouth of Truth (at your own risk!). Give her the kind of royal treatment she deserves at Otello alla Concordia, a vine- and lantern-covered courtyard restaurant that serves timeless Italian dishes like saffron gnocchi and grated fennel orata. End the evening on a sweet note with a gelato on the nearby Spanish Steps. When in Rome…

The cool predatory charm and between-the-sheets know-how of an older woman is sure to shake you out of your post-graduate blues. Meet your Mrs. Robinson–style seductress for a drink at the Langham Huntington Pasadena’s low-lit Tap Room, then go for a dip in the heated saline swimming pool, which is open late during the summer. Or take a romantic walk around the hotel’s 23 acres before heading up to one of the hotel’s luxurious guestrooms. Not one for pillow talk, your temptress is sure to give you the sex education you missed in school.