Cheap dates: Boston South
Hyde Park'll make ya – jump, jump!
A 25-minute drive from downtown, Sky Zone Sports stretches the limits of what can reasonably be described as Southern Boston. It's worth a trip, though, for the chance to cavort on trampolines and literally bounce off the walls. (Only the ceilings lack springs.) The “Sky Jam” Saturday night special is $15 for an hour and a half of jumping, plus pizza and soft drinks—though we recommend jumping before chowing down. Newly single? Sky Zone is perfect if you're looking for a rebound with a rebound. 91 Sprague St, Hyde Park (857-345-9693, boston.skyzonesports.com)
Castles, airplanes and sea monsters
Southie may be best known for grimey dives and baby-faced math-genius janitors, but the 'hood's got some outdoorsy beauty, too. Fort Independence Park—you probably know it as “Castle Island”—boasts grassy knolls and cozy beach spots while also being within earshot of Logan Airport's landing docks. On summer weekends you can tour the spooky fort itself, which has a history of supposed sea monster sightings. Be sure to swing by Sullivan's for some soft-serve and a plate of crinkle-cut fries. Sullivan's: 2080 Day Blvd, South Boston (617-268-5685, sullivanscastleisland.com)
Get on your bike
The Pierre Lallement Bicycle Path is an oft-overlooked route that traverses 3.5 miles. It passes over six Orange Line T stops between Back Bay and Forest Hills, giving it a nice mix of scenic and city views. Landmarks abound, from Prudential Center to Symphony Hall, but the prettiest stretch extends along the brownstones and gardens of the South End. You'll also pass Northeastern's tennis courts if you're looking to sneak in for a set. Those gutsy enough for a night ride should stop by cyclist watering hole Delux Cafe afterwards for a stiff drink. Delux Cafe: 100 Chandler St, South End, Boston (617-338-5258)
The sexier side of trivia
Looking to break the ice? The Savant Project's “Sex & Drugs” trivia nights on Sundays will pulverize it instantly. Sample question: “is this photo of a baby toy, or a sex toy?” Best the competition, and you could win a daily drink for a year. Chomp on beer-steamed mussels or polenta lasagna while you suck down the “Miller Mosa,” the Savant's classy blend of OJ, orange Curacao, and Miller Genuine Draft. Just don't lose focus on the prize—namely, impressing your date with your supreme sex (IQ) skills. 1625 Tremont St, Mission Hill, Boston (617-566-5958, thesavantproject.com)
Go gallery-browsing in SoWa
On the first Friday of every month, dozens of art galleries south of Washington Street in the South End open their doors—and, often, their wine cellars—and invite the public to schmooze with artists, scarf down free hors d'œuvres and explore some of the city's best exhibits. Even art noobs will get a kick out of roaming the streets of SoWa and watching all the beautiful bohemians nod pensively at canvases. With the right timing, you might even be able to couple your activities with a beer tasting at South End Formaggio. South End Formaggio: 268 Shawmut Ave, South End, Boston (617-350-6996, southendformaggio.com)
