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Couples in the City: Date Ideas to Make Your Summer In (Or Near) 7 Major Cities Even Hotter

Manage to conveniently land a job or pick up a few summer classes in the same city as a special someone? Or maybe you’re itching to leave the school year behind, and the intern you’ve been eyeing in the sandwich line is just the way to do it.

You’re likely working hard at your job, or, perhaps, you’re hardly working on much but your love life and your tan. Either way, this is summer vacation. So, whether you’re rekindling a steady thing or embarking on a summer fling, you two should be enjoying yourselves. To aid in the process, here’s a guide to some date ideas that’ll help ensure a good time in seven popular U.S. cities — without breaking the bank or getting you fired in the process.
 
NEW YORK CITY
LOS ANGELES
WASHINGTON, D.C.
CHICAGO
BOSTON
SAN FRANCISCO
PHILADELPHIA

 

NEW YORK CITY
To generalize, this cluster usually includes those working in finance, consulting, PR, fashion, marketing, media, publishing, real estate, law, nonprofits or anything else corporate. And, like most things in New York, the workplace can be an intense one. Perhaps the world’s most popular and crowded place to intern, there’s a reason why the future yuppies of the universe flood the Big Apple each summer, sweating it out in NYU dorms and cringing at the $5 froyo (plus extra for toppings.) There is more going on than you can conceivably take in — particularly when you’re poor and/or overworked. But, from up-and-coming Brooklyn to traditional Broadway, there are plenty of worthwhile romantic adventures.
 
Save: Ice Cream and A Cruise
Strange and tacky as this may sound, you can enjoy a free water taxi ride [http://www.nywatertaxi.com/Rides/ikea/] from Manhattan to Brooklyn on the weekends, via the blue and yellow IKEA shuttle.  While it’s not exactly the most romantic, it’s guaranteed to be much cheaper and novel than any taxi ride. So line up at Pier 11, head to IKEA, and enjoy one (or several) $1 ice cream cones. 
 
Live: Browse Brooklyn
You may not have time or funds to start a tab at the Empire Hotel or sneak off to the Hamptons for the weekend in true Gossip Girl style. But BK (not to be confused with Burger King) is quickly becoming a hangout hot spot. Hop on the subway and cross the bridge, where there’s plenty more to do than stare at hipsters and go to IKEA.

  • Spend an afternoon treasure hunting at Brooklyn Flea: Open Saturdays (in Fort Greene) and Sundays (in Williamsburg,) the outdoor flea market is full of an acre’s worth of antiques, vintage clothes, crafts, jewelry and some of the city’s best grub.
  • Picnic at Prospect Park, and people watch on Bedford Avenue.
  • Check out the Botanic Garden—you’ll get in for free on Saturdays from 10 to noon.
  • Click here for more insider’s tips and creative ideas.

Splurge: Rooftop Hop
What Manhattan lacks in backyards, it attempts to make up for in rooftop terraces. So head to hotels, bars, or the apartment of your lucky NYC friend with a terrace, and take in the sun, the view and some food or drinks. You generally don’t have to spend a lot to hang out up there, and you can feel important while people watching the swanky folk (and likely some celebrities) who do spend a lot. If you’re not 21, some places will only let you up there during the day, but it’s still worth it for the view, the sunset and the pleasure in feeling like you’re finally on top of your boss for once. Click here for some of the city’s coolest spots.
Also, find a guide to eating well as an intern here.
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LOS ANGELES
Somewhat similar to New York City (both are cupcake- and froyo-filled) but with a Hollywood/West Coast twist, LA attracts many an intern trying to break into entertainment and acting, students who enjoy palm trees, aspiring plastic surgeons and the occasional surfer. And, while a summer in the land of pretty people has the potential to mess with your self-confidence, there are plenty adventures where you two can be the stars.

Save: An Evening with Jimmy Kimmel
Staying home and watching Jimmy Kimmel Live!makes for a pretty mediocre date, but getting free tickets to go to the taping and sitting in the audience while Jimmy chit chats with A-list celebs can make for a more special Hollywood evening. Reserve tickets to spend the night as Jimmy’s guest, and also enjoy a bonus live performance from the closing band.  
 
Live: Take a Hike Through Pasadena
Ten miles from downtown LA is Old Pasadena, a nice retreat from city life. Hike up the Mount Lowe trail at the top of Lake Avenue, where you’ll get some pretty sweet views of downtown LA. If you’re into art, check out the Norton Simon Museum (free if you bring along your student ID!) Then, stroll through charming Old Pasadena, and stop at a bistro to enjoy a romantic dinner or dessert.
 
Splurge: The Disney Date
You’re old and working now, but who doesn’t still love Mickey? Get day passes to Disneyland, and spend the afternoon screaming on Space Mountain, eating all that fair food that’s super crappy for you and hanging with some of your childhood (and adulthood?) favorites. For $76 for a day pass, it’s not the cheapest of outings, but you can’t really put a price on Disney magic.
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WASHINGTON, D.C.
The Capital brings plenty of future politicians, lobbyists, policymakers, lawyers, historians and probably a few secret agents-in-training to town each summer. But, even for the government lovers of world, there’s much more to do than tour the Hill and talk politics.
 

Save: Millennium Stage Music
Like seeing live concerts or at least trying to soak up some culture? Well, you can—and for free — at 6p.m. every night at D.C.’s Kennedy Center. The performances range in their crowds and types — everything from jazz to rock to slam poetry. And if you and your man are fans of JFK, you can think about him all concert long, as his memorial is funding your evening. Just check the schedule beforehand and show up, no tickets necessary. Still have energy after the show? Take your own evening walking tour of the monuments or check out some of these other free things to get up to.
 
Live: Paddle The Capital
Summer in D.C. is hot and humid, but, if you’re into the cliché and classic day dates, cool off on the water with a paddle boat ride around the Tidal Basin, the cherry blossom-laced reservoir between the Potomac and the Washington Channel from which you get a clear view of the Jefferson Memorial. It’s $12 per hour for a two-person boat. 
 
Splurge: Hang Around Georgetown
Not just a college town, historic Georgetown boasts tons of upscale dining, shopping and a beautiful waterfront. Grab drinks or dinner outside overlooking the Washington Monument. Then, stroll through the quaint and classy town, admiring the beautiful houses and stopping at Baked & Wired — a bakery better than Georgetown Cupcake — and share some dessert (though you’ll most definitely want your own.)
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CHICAGO
The New York of the Midwest, Chicago’s yet another business district and college city that brings in loads of ambitious students every summer. And, more than just a land of pop and Barack Obama’s old residence, Chi-town is full of history, art, parks and adorable adventures.

Save: Pizza and Pets
Along with being one of the oldest zoos in the nation, the Lincoln Park Zoo is also one of the few free ones. Spanning 35 acres of Lincoln Park, there are more than 1,200 animals to visit. When you’re done chilling with the polar bears, gorillas and penguins, dine Chicago-style with some deep dish pizza at Giordano’s
 
Live: Ferris Wheel Fun
Take a nighttime ride on Navy Pier’s famous 150-foot Ferris wheel ($6 a person for a seven-minute ride,) and then make your way around the park’s other rides, grab some food, and go mini golfing. If you’re more about the virtual rides, see a movie in IMAX for about $15 a ticket. But if it’s a Wednesday or Saturday, be sure to make it outside for the 9:30 p.m. and 10:15 p.m., respectively, summer firework displays.
 
Splurge: City by Segway
Chicago’s a big place, with lots of sites and water to be seen, and when you’re cruising on a Segway, you can cover all the more ground. Try the Lakefront Tour, where you’ll get to check out Grant Park and get awesome views of the skyline, Millennium Park and Adler Planetarium without walking a step. That’ll cost you $49-$69 a rider, and you can end the evening with a Greek dinner at the Athenian Room in Lincoln Park. Tina Fey loves it, and you and your significant other probably will, too.
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BOSTON

Like Philly, historical Beantown is student central all year-round, and, come May, there are loads of summer school students along with a good deal of professional interns, research assistants and aspiring doctors and scientists. And, while people drive like Massholes, so long as you don’t root for the Yankees, you’ll likely live to see Harvahd, eat some chowda and experience many great dating adventures.

Save: Little Italy
For an evening out that doesn’t cost you a day’s pay (or does if you’re unpaid,) head to Boston’s Little Italy in the North End, with cobblestone streets and millions of calories and carbs in the form of homemade breads, pizzas and pastas. Stop at Regina Pizzeria, a casual but special joint. Then, walk around, hope that he buys you a rose from one of the peddlers, and follow the trail of Bostonians’ and tourists’ little white takeout boxes to the storefront of the famous Mike’s Pastry, where you pretty much have to get some dessert (especially a cannoli.) You can then walk toward the harbor, admire the waterfront, and people-watch your way through Quincy Market.
 
Live: Boston Duck Tours or Red Sox Nation
The idea of touring Boston in a boat-truck in the spirit of ducks might not sound all too romantic, but the city’s famous downtown water-and-land Duck Tours are not only comical experiences sure to make you and your boy bond, but, for $27 a student ticket, they’re also an incredible way to see the city. The tours take you past 36 Boston attractions with descriptions from your ConDucktor (brace yourself for duck puns.) If you can’t bring yourself to ride on a boat-car for an hour and a half, you should a) be punished, and b) at least get to Fenway Park, where baseball, history, hot dogs and Boston spirit collide in what promises to be the most fun nine innings of your life. Most tickets don’t come cheap, but you can usually snag a pair of nosebleeds for around $50. So head for Yawkey way, grab a few franks, and you’ll be able to soak up the experience, sing during the seventh-inning stretch, and, if you’re extra lucky, maybe even make it onto the kiss cam.
 
Splurge: Lobstah in Gloustah
Cape Cod, Nantucket and Martha’s Vineyard are popular summer destinations for Bostonians, but an hour ride away in the other direction via the commuter rail is Gloucester — also home to a beach that lets you swim in the freezing Atlantic. Once you finish sunning and swimming at an area beach like Good Harbor, walk through the nearby seaside town of Rockport, perusing local art galleries and stopping for some lobster rolls and homemade salt water taffy.
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SAN FRANCISCO

Home to Stanford, Berkeley, Google and Apple, there’s no deficiency of young, relaxed smarties in the Bay Area. With a waterfront, mild climate and plenty of farm-fresh, Cali-style grub (mmm artichoke and avocado,) there’s more to get up to than biking the Golden Gate.
 
Save: Picnic With the Painted Ladies
Home to Ghirardelli Chocolate and lots of organic goodness, San Fran doesn’t mess around with its grub — a fact that’s more than obvious after a visit to The Ferry Building. Check out the famous marketplace to pick up goodies and some Napa-made wine for a picnic (and stock up on vendors’ free samples as appetizers while you’re at it.) There’s plenty for him (“Tasted Salted Pig Parts”) as well as for your sweet tooth (Miette Bakery). If you go on Tuesday, Thursday or Saturday, there’s a Farmers Market so delicious that it’ll make it hard for you to make it to your next destination. But, if you can restrain yourself, take the trolley to Alamo Square Park, and enjoy your picnic sitting atop the famous hill, overlooking the Painted Ladies and San Fran skyline. When you’re done eating and admiring the Victorian homes that may well remind you of when you used to watch Full House, walk along Haight Street and pop into small Deadhead-themed shops that’ll make you feel like you’re back in the 60s and 70s.
 
Live: San Fran Style Parody
If you like San Francisco, comedy, pop culture, singing and crazy hats, a viewing of Beach Blanket Babylon, the longest running musical revue in the country, is definitely worth your time. Buy a set of tickets (~$40 each) in advance because the musical spoof has had sold out shows since 1974. The evening performances are Wednesday-Friday at 8 p.m. and Saturday at 6:30 p.m. and 9:30 p.m., though be warned that people under 21 are not admitted to evening performances. The show runs at an intimate little theater in North Beach, just a minute’s walk from a fun shopping and dining center. If you guys love garlic and want a fun dinner before the show, try The Stinking Rose (a nearby garlic restaurant.) Just don’t plan on making out afterward … or at least bring some mints if you do.
 
Splurge: Cruise the Coast
If you think the city itself is hilly and scenic, you’re in for quite the upgrade when you head south or north. There’s Napa and wine country, but for a less pricey and equally gorgeous weekend getaway, treat yourselves by renting a car (try ZipCar, where car hourly rates start at $7.75 after you pay annual and application fees) and driving straight down the Pacific Coast Highway, blasting music and taking lots of breaks at the regular stop-offs and charming beach towns. Pass plenty of cows and the farm-filled town Castroville, the artichoke capital of the world, and then take the 17-Mile Drive through famous Pebble Beach. If you’re feeling ambitious, end an evening with dinner at Nepenthe Restaurant in Big Sur, where the food is pretty good, but the view is just great.
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PHILADELPHIA

This old Quaker city sometimes finds itself overshadowed by nearby NYC. But come summer, and it’s full of students, many taking classes, doing research at hospitals or with professors and getting into all sorts of things. Desirable in its affordability, it’s the City of (“Brotherly?”) Love, and with a big art scene, a BYOB culture and a lot of history, there are plenty of charming dates to be had that don’t (or do) involve cheesesteaks.
 
Save: Rock the Art Museum
There are only so many times you can look at the Liberty Bell, but those famous steps at the Philadelphia Museum of Art not only include a sophisticated set of exhibits, but also lead out to a beautiful Azalea Garden and the Schuylkill River, so even wandering outside the museum makes for a nice afternoon. On the first Sunday of each month, you get to pay “what you wish,” so make a small donation and save up for a sundae at the acclaimed Franklin Fountain or gourmet gelato at Capogiro.
 
Live: Raid Reading Terminal
You know the scene in National Treasure when Diane Kruger is hiding from the bad guys behind a counter in a marketplace? She so happens to be at Philadelphia’s Reading Terminal —  one of the best indoor marketplaces of its kind, with dozens of area vendors selling everything from Amish pretzels (sold to you by the Amish creators themselves) and cheesesteaks to homemade Italian cannoli and fresh produce. Go for lunch, sample a bit of everything, and then buy ingredients for a fresh vegetable pasta or steak dinner to prepare together later in the evening.
 
Splurge: Tour De Tapas
Boasting a surprisingly incredible restaurant scene, Philadelphia is all about the BYOB and tapas-style dining. With so many places in such close proximity, it’s a tough call. So don’t feel limited to one place. To spice things up, decide to treat yourselves to a five-course meal, starting with drinks and an appetizer at Tinto right on Rittenhouse Square. Move on to Barbuzzo for a Mediterranean dish, and if it’s crowded, sit at the bar. If you like modern Mexican, walk down the street to Barbuzzo’s sister restaurant, Lolita, and split a main dish and a pitcher of its famous margaritas. If you’ve got room for dessert, head back toward Rittenhouse Park and finish up your feast with dessert outside at Parc or Alma de Cuba. Yes, you’ll be that annoying couple that orders very little, but warn each place that you’re there for light fare, tip generously, and play the whole “I’m a poor college kid” card. After you’re done consuming, stroll around Rittenhouse to start walking off some of the damage you’ve likely done.
 
Know of other good date spots in these cities? Other cities? Comment below to fill HC readers in on some of your favorites. Happy dating!
 

 
 

Katie most enjoys friends, non-fiction, and dessert. She graduated from University of Pennsylvania and is a contributing editor at Glamour magazine.