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  • A A good test of how well you know your city is how well you can play tour guide. There’s more to Boston than Harvard Square, or your favorite bar for that matter, so we’ve put together 10 mini guides to the best of the city’s neighborhoods, and great times to hit them up.
    Morning
    Courtesy of Brooklyn Boulders Somerville

    Morning

    Union Square

    8am: Hit up Union Square Donuts
    There are no sweeter words in the English language than “small batch donuts.” This locally renowned donut shop sells out of their favorites early (maple bacon, people!) so get there as close to the 7am opening as you can. View on Map

    10am: Use that sugar buzz at Brooklyn Boulders
    They say donuts are the best prelude to indoor rock climbing, so head up the street to this 40,000 square-foot climbing facility, and discover your inner rappeler. View on Map

    12pm: Refuel at Aeronaut Brewing
    Every rock climbing facility should be built next to a brewery. One door over you can sample local beer and maybe catch some live music. View on Map

    Jamaica Plain

    10am: Take a jog around Jamaica Pond
    Laps are boring, unless you’re lapping a picturesque body of water right in the city proper. Also? Jake Gyllenhaal has been spotted working out here ahead of the next Boston Marathon movie. No harm in checking out his routine, right?

    11:30am: Indulge your two favorite pastimes at Tres Gatos
    Those pastimes, of course, being tapas and secondhand records. This Centre Street restaurant is all small-plates business in front (morning-time deviled eggs and chicken liver toast, together at last) with a small used music and bookstore in back. View on Map

    1pm: Gallery hop on Centre/South Streets
    Take a long stroll down JP’s main thoroughfare to hit up three indie art galleries: Aviary, The Hallway, and UForge, all open on weekends, all displaying locally spun artworks. You might even luck into an art class. You could be next!

    Allston/Brighton

    10am: Replicate the Harvard Stadium November Project workout
    Did you know that the November Project began in Boston? Alas, its most venerated workout takes place on this stadium’s steps … at 5:30am and 6:30am. Go to the website and then recreate the WoD at a slightly more reasonable morning hour. View on Map

    11:30am: Carbo-load at Lulu’s Allston
    You haven’t brunched until you’ve Hoover-ed Lulu’s White Trash Hash, a glorious pile of tater tots, braised short ribs, poached eggs, and hollandaise sauce. View on Map

    1pm: Find your inner skate rat and art collector at Orchard
    Freebies are always a lure, which means that the first-floor miniramp at Orchard skate shop is a must-do -- as is a perusal of the gallery on the second floor. View on Map

    Todd Van Hoosear/Flickr

    South End

    11am: Have a pre-noon beer at SoWa Market
    The May opening of the SoWa Market is the official kickoff to summer. After chatting with local farmers, testing samples of organic ice cream, and snooping around the vintage market, you can beat a retreat into the new beer and wine garden for a regionally brewed Tall Boy. View on Map

    12pm: Splash some cash on Tremont Street
    The South End is that rare bird that boasts an equal number of male- and female-centric clothing boutiques, plus funky gift and accessories shops like Niche, and Olives & Grace. Everybody wins!

    2pm: Scarf down poutine at The Gallows
    Shopping is hard work, but gravy and fries can cure what ails. One block down on Washington Street, The Gallows dishes up a killer brunch that includes the Sunrise Poutine -- a pile of eggs, country ham, fries, gravy, and curds. View on Map

    Afternoon
    Shutterstock

    Afternoon

    Back Bay

    12:30pm: Get your culture on in the Boston Public Library Courtyard
    Tucked inside one of the city’s most architecturally woah buildings is a Parisian-like atrium where, on warmer-weather Fridays, you might luck into some live jazz or classical music, for free. View on Map

    1:30pm: Savor oysters and some rosé at Select Oyster Bar
    Just around the corner is one of the neighborhood’s most exciting restaurant openings in years, and your best bet for expertly prepared New England seafood. Cross your fingers for a back patio table and ask for wine recommendations -- they pour specials both by the bottle and the carafe. View on Map

    3:30pm: Thrift shop on Newbury Street
    There’s a special joy in hitting up secondhand shops on a famed boulevard that also houses Versace, Chanel, and Giorgio Armani. Relish beating the system at the just-opened men’s consignment shop from 2nd Time Around.

    Fort Point/Seaport/Innovation District

    4pm: Grab a growler at Trillium Tasting Room
    It’s not a tasting room per se, but rather a lilliputian window (well, door) into one of the great local brewing hive minds. Chat with the beermakers and then carry out your favorite IPA in an economy size. View on Map

    The Lawn on D/Facebook

    5pm: Show off your cornhole technique at Lawn on D
    An outdoor event space with swings, art installations, lawn games, and drinks, LoD became the summertime gathering place last year. Your only worry is waiting for your turn on one of the glow-in-the-dark swings. View on Map

    7pm: Celebrity spot at Legal Harborside's rooftop
    Head back towards the harbor for some glam high-rise drinking overlooking the Boston Harbor. Sure, there’s velvet rope entry on the first floor, but the view and social scene are worth the wait -- and you are somebody. View on Map

    Evening
    Shutterstock

    Evening

    South Boston

    5pm: Drift off Carson Beach
    Somehow even us locals forget about the watersports right here. Boating in Boston sets you up to kayak or paddleboard right off the beach into Dorchester Bay.

    7pm: Split a lobster roll and some soft serve at Sullivan’s
    Sully’s is as Southie as it gets (i.e. Whitey Bulger was once a regular patron). Yeah, the lines might be out the door, but the lobster roll is actually one of the city’s great deals, and who can resist a vanilla-chocolate twist? View on Map

    9pm: Experience the “new” South Boston at Loco Taqueria and Oyster Bar
    West Broadway is in the midst of a dining renaissance; for our money, any place that serves you terrific tacos (seared venison, root beer-braised chicken) and local bivalves is a keeper. View on Map

    digboston/Flickr

    Harvard Square

    5pm: Elevate your drinking game -- literally -- at Daedelus
    Patio drinks are great, but rooftop patio drinks are even better. Daedalus flies under the radar, which makes for relaxed beers and sky gazing. View on Map

    7:30pm: Travel back in time at In Your Ear!
    The demise of record shops has been greatly exaggerated. In Your Ear! is well into its fourth decade and still attracting the city’s best rock snobs. View on Map

    9pm: Hit up The Sinclair for live music
    With your rock proclivities whetted, it’s time to head back down Brattle Street to Harvard Square’s greatest new venue, a cavernous industrial space attracting local and national acts. Also? There are three, count ‘em three, bars inside. View on Map

    Fenway

    7pm: Spring for a same-day seat to a Red Sox game
    Yes, they’re some of the most elusive tickets in town, but that doesn’t meant they’re impossible. Ninety minutes before gametime, the box office releases a limited number of seats at E Gate. And if you’re still out of luck, let’s just say that scalped tickets are *not* hard to come by. View on Map

    10pm: Get out some post-game aggression at Blazing Paddles
    Susan Sarandon has not cornered the table tennis market. Once you’ve departed Fenway, you merely need turn the corner to locate the city’s only ping pong bar. View on Map

    11pm: Stick a straw in a classy scorpion bowl at Hojoko
    High-end izakayas are totally a thing, and this one can be found inside a cool hotel. You and your compadres are best served going for the “large-format” cocktails, be it a Blue Hawaiian (plantation rum, pineapple, mizu sochu, lemon, blue Curacao) or the Surfer on Acid (Appleton rum, clément coconut, pineapple, Peychaud’s, absinthe). View on Map

    Inman Square

    8pm: Nab a coveted seat at BisQ
    The best spots at this much-lauded restaurant are tucked away in a semi-hidden back room, where you can meet local oenophiles -- the wine list here is on point -- while working your way through the menu’s extensive charcuterie list. View on Map

    9pm: Have a Latin dance party at Ryles
    At least three days a week, this jazz club brings in local DJs to play a muy caliente mix of salsa, bachata, merengue, and zouk. View on Map

    Midnight: Get a nightcap at Trina’s Starlite Lounge
    Replenish yourself after all that dance floor action at Trina’s, a pretension-free faux dive that’s a favorite hangout among area restaurant workers -- always a solid endorsement. View on Map

    SELECT Oyster Bar
    $$$ Back Bay
     

    Michael Serpa, formerly of Neptune Oyster, is behind this Back Bay seafood restaurant in a brick townhouse. Select is a seafood lover's paradise that produces daily ceviche, crudo, and grilled fish mains....more

    Trillium Brewing Company
    $$ Fort Point Channel
     

    Because apparently working full-time jobs, opening a fitness business, and raising two young kids wasn't keeping them busy enough, the quite-possibly-insane super-couple behind Trillium has spent the last...more

    The mother of all Legal Sea Foods, Legal Harborside is the upscale seafood chain's flagship restaurant on the Boston Waterfront. The 20,000sqft space takes over three floors, each with a different concept....more

    The Gallows
    South End
     

    Although its name is morbid, this South End spot is anything but. Rowdy groups flock in numbers for classic and craft cocktails, drafts, and a small sampling of wine. Those who aren't taking advantage of t...more

    Hidden away on Tyler St (not far from Union Sq) lurks Aeronaut’s secret beer laboratory and local sustainable foods co-op. Within these techno-chic walls you can enjoy eight rotating drafts of Aeronaut's s...more

    Union Square Donuts
    $ Union Square
     

    Union Square Donuts is a charming, unassuming counter-serve in Somerville that is well on its way to knocking Dunkin' off its throne with a variety of specialty doughnuts. Each doughnut is thick and fluffy...more

    The Baja menu at this Southie spot emphasizes bright and summery tacos and inventive oyster dishes. Loco's fried fish taco has a tropical edge thanks to a topping of pineapple aioli, while oysters -- when...more

    Daedalus
    $$ Harvard Square
     

    This pretty pub serves up better-than-you'd-expect-from-a-pub fare and, between the roofdeck and the lower bar area, offers lots of different spaces for eating and drinking.

    The Sinclair Kitchen
    $$ Harvard Square
     

    Rocking out in Harvard Square, the music promo dudes at The Bowery overhauled the former Phatt Boys into a 500-plus capacity, industrial-aesthetic'd concert venue/ rustic bar & kitchen/ casual-cool rooftop...more

    Hojoko
    $$ Fenway-Kenmore
     

    Located in Fenway's swanky Verb Hotel, comic-inspired Hojoko serves up Japanese fare with pub style -- over a game of pacman or galaga on an old-school arcade machine (which you'll probably use as your tab...more

    The exterior of Trina's Starlite Lounge looks like your typical dive (could it be the Miller High Life sign?), but once inside, you'll discover a hip, retro-style diner and bar that's serving up killer tak...more

    Contrary to popular belief, BISq is not a soup shop, instead it's an inviting, upscale small plate restaurant with an impressive wine list and none of the pretension. Although it specializes in charcuterie...more

    Tres Gatos
    $$ Jamaica Plain
     

    Fresh off celebrating their two-year birthday, the folks at JP's popular tapas/wine bar/book & record shop are celebrating that age where you ask annoying questions you couldn't possibly understand the ans...more

    Lulu's
    $$ Allston-Brighton
     

    This spacious, industrial-looking American eatery is filled with over 50 craft beers and delicious comfort food like the Bad Ass Burger -- natural beef with herbs & butter, short ribs, and a runny egg that...more

    Like many things in Boston, the main branch of the Boston Public Library is very old and very beautiful. The Copley Square location has been open since 1895, which we'd say is a pretty good run. Make sure...more

    SoWa Market
    $ South End
     

    The SoWa Market is a celebration of summer in a hippest, artsiest way possible. Vendors skew towards the hand-made, artisanal variety, with a healthy dose of local farmers and food trucks. The market feat...more

    Lawn On D
    $ Fort Point Channel
     

    Lawn on D is a outdoor gathering space open for live events, featuring regular concerts and cool light-up crescent-shaped swinging chairs. They offer a ton of games like ping-pong and bocce, plus some high...more

    Brooklyn Boulders
    $$ Union Square
     

    Brooklyn Boulders is a one-stop shop for climbing gurus, with an extensive series of climbing walls, along with a cardio and weights gym.

    Harvard Stadium
    $ Allston-Brighton
     

    The best place to see the Harvard Crimson, one of the football teams in the world, Harvard Stadium has a lot of history behind it. This field is actually the reason why the forward pass was legalized in fo...more

    Orchard Skateshop
    $$ Allston-Brighton
     

    The one-of-a-kind Orchard Skateshop is truly a by-the-people, for-the-people endeavor. It's entirely skateboarder-owned, which is reflected in their sponsorship of local riders and video production efforts...more

    Sullivan's (or Sully's, if you want to sound local) is a venerable food stand on Castle Island. Stop by for one of the best lobster rolls in Boston, one of their Sully's Snap Dogs, or soft-serve ice cream....more

    In Your Ear!
    $ Harvard Square
     

    Self-described as "the little store that could," In Your Ear! is a testament to the power of indie record stores. Offering original vinyl records, CD's, and posters, IYE carries on the tradition of great l...more

    Fenway Park
    $ Fenway-Kenmore
     

    Located in the heart of Boston's Kenmore Square, Fenway Park has been home to the Boston Red Sox (and the famous Green Monster) since 1912.

    Game On
    Fenway-Kenmore
     

    90 HD TVs, bars both upstairs and down, and delicious snacks like loaded steak fries and Asian BBQ pork riblets, make Game On! the perfect place to get your game on. Bonus points for the ping pong tables a...more

    Ryles Jazz Club
    $ Inman Square
     

    Ryles has been in Cambridge since 1919, practically since the invention of jazz, so they know what they're doing. The first floor hosts live performances from national and local talent, and the second floo...more