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Trying to mix the classy with the touristy. These are the places I recommend most to visitors, including spots in Brookline, Allston, Brighton, Cambridge and Somerville.
Seafood Restaurant · Kenmore · 304 tips and reviews
Jenny Mackintosh: The stars align at the bar. Don't be afraid to ask for advice on a new favorite based on your old ones. Some of the best cocktails and seafood in the city are served here.
Art Museum · Medical Center Area · 175 tips and reviews
Jenny Mackintosh: This museum is a city jewel. A very unique, even romantic experience. Don't miss the gift shop (well-curated, beautiful finds for gifts & home).
Jenny Mackintosh: You could spend a whole afternoon here (and I recommend it), but if you don't have that kind of time, visit the harbor seals in the outdoor tank for free.
Jenny Mackintosh: Charred, chewy crust and some classic and unusual topping combos await you here. Try the Alsatian (bacon, onions, gruyere and garlic), and save some room for their ice cream if you can.
Music Venue · Harvard Square · 22 tips and reviews
Jenny Mackintosh: A legendary folk venue where you'll get well-acquainted with your neighbors. Get a ticket to a show and order food from the adjoining Veggie Planet (Henry's Dinner & coconut rice: oddly addicting.)
528 Commonwealth Ave (at Kenmore Square), Boston, MA
American Restaurant · Kenmore · 304 tips and reviews
Jenny Mackintosh: Try an Old Cuban (rum, lime, simple syrup, mint, bitters, and bubbles). The smack of the mint leaf to release the oils onto the rim is fun bar theater.
139 St. James Ave (Boylston St. and Dartmouth St.), Boston, MA
Farmers Market · Back Bay East · 13 tips and reviews
Jenny Mackintosh: Open Tuesdays & Fridays May-November. Be sure to visit the Crystal Brook Farms booth early and get a goat cheese picnic (marinated goat cheese, bread, and trail mix). Take your lunch to the lawn.
9 Arlington St (btwn Beacon & Boylston St), Boston, MA
Garden · 200 tips and reviews
Jenny Mackintosh: Bring a blanket for lounging, a book for reading, and cash for the swan boats (a touristy diversion for only $3). Bonus points for being here during tulip season.
Jenny Mackintosh: It's tough to name specifics here (lots to explore, and you should wander down main streets & side streets to get the vibe.) If I had to guide you, I'd say try Felipe's, L.A. Burdick, & Club Passim.
Jenny Mackintosh: The lavender macaron, wrapped in a piece of wax paper for carrying, is the perfect chic treat. Pair it with a small dark chocolate and wander Harvard Square feeling decadent.
Indie Movie Theater · Coolidge Corner · 73 tips and reviews
Jenny Mackintosh: Few places take pride in the magic of the movies like the Coolidge. They carry some of the best new selections, along with older classics (check out their schedule for special events).
New American Restaurant · Coolidge Corner · 72 tips and reviews
Jenny Mackintosh: The tips don't lie: the bacon-wrapped dates are delicious, as are their scallops if they have them. Get a dish of olives with your drink if you sit at the bar.
4 Jersey St (btwn Lansdowne St & Van Ness St), Boston, MA
Baseball Stadium · Fenway - Kenmore - Audubon Circle - Longwood · 740 tips and reviews
Jenny Mackintosh: Even if you're not a fan, you'll have a hard time not getting swept up in the romance of baseball here. Come for a tour or a game (you can buy tickets at Gate E 90 minutes before the game.)
263 Hanover St (btwn Cross & Richmond), Boston, MA
Pastry Shop · North End · 159 tips and reviews
Jenny Mackintosh: The lobster tails could feed at least a couple people each. Their truffles are to die for. Can't really go wrong here, and the line is usually much more manageable than Mike's.
296 Hanover St (btwn Parmenterr & Prince), Boston, MA
Café · North End · 143 tips and reviews
Jenny Mackintosh: Order a cappuccino and maybe dessert, turn off your phone for a while, and get that North End feeling you were looking for. Especially good on rainy days.
Jenny Mackintosh: Brunch is pretty serious here. Order the biscuits & gravy or the skillet fries. May as well order a bloody Mary or a cocktail while you're at it.
Jenny Mackintosh: The Pollo Involtini is to die for. Port wine reduction over chicken breasts stuffed with spinach, fontina and prosciutto. The penne & sauce on the side is a bonus. Delicious.
476 Commonwealth Ave (btwn Charlesgate & Kenmore St.), Boston, MA
Bar · Kenmore · 112 tips and reviews
Jenny Mackintosh: Cash only and tough to hear yourself think on a game day, but worth it for the tater tots and craft beer list. Get a hot dog with mango salsa and guacamole, or with mac & cheese (really).
Belgian Restaurant · Downtown Boston · 133 tips and reviews
Jenny Mackintosh: Order a cone of the frites -- or the poutine if you'd really like a food coma. They also make liege waffles for dessert -- try the salted caramel.
Jenny Mackintosh: Craft beer superfans, rejoice. This is where even the most discerning beer drinkers can find something they haven't had before. Try the fries with roasted garlic aioli or the pretzel w/ beer cheese.
178 Thorndike St (at Commonwealth Ave), Boston, MA
Bakery · 60 tips and reviews
Jenny Mackintosh: Ok, I can't believe no one has posted a tip yet about the currant doughnut! Super soft and pillowy, rolled in superfine sugar. Food & Wine called it one of "America's Best Doughnuts."