Start at Hynes Convention Center (the Green line T stop at the top of Newbury); walk down Newbury Street amongst all the college students. If you’re a sucker for a great view, take a detour at Fairfield Street and head up to the Top of the Hub for a great view of Boston. At Dartmouth Street, go one block to your right to Boylston, check out the statues in front of the library, and then the Trinity Chapel in Copley Square. Walk through City Hall, and pick up the Freedom Trail if you’re a history buff. Don’t go much further than the Charlestown Bridge; not much to see once you’ve passed that. At least try to see Paul Revere’s house, a 17th-century home overlooking a picturesque cobblestone square.
Now jump on the T and go on over to Cambridge for the evening!
Start at Central and bar crawl to Harvard Square. In Central there’s the Cantab (divey and cool), the Miracle of Science (pretty good food if you haven’t eaten yet), the Enormous Room, the Middle East and TT’s (both legendary joints for live music), River Gods (good food and good Guinness) and the Field. If you don’t mind waiting in line, grab a burger and some onion rings at Mr. Bartley’s Burger Cottage (1246 Massachusetts Ave).In between Central and Harvard, don’t miss the People’s Republik, which has a bomb hanging from the ceiling.
In Harvard Square, hit up Grendel’s (cheap happy hour fondue!) or Shay’s. End up at Charlie’s Kitchen; go upstairs and watch the rest of the Sox game with a bunch of rowdy Bostoners. Harvard Square in general is a fun area to check out if you like shopping or people watching. Harvard Square also has some great ice cream if you just want to walk around and people watch. Try Herrel’s (Dunster) or JP Licks (Mass).
The North End is another must visit: home to the famous North Church and full of Italian flavor. Walk up and down the streets, have some great Italian food, stumble to Mike’s Pastry and get some deserts and make your way home. A few restaurants to look out for are Neptune Oyster (Seafood, 63 Salem St), Giacomo’s (Italian, 351 Hanover Street), Pomodoro (Italian) and Galleria Umberto (Pizza, 289 Hanover Street).
For a great Lobster Roll try Belle Isle’s roll (1267 Saratoga St East). The buttery, griddle-crisped hot dog bun brilliantly holds its own against the tender tail, knuckle, and claw meat stuffed inside. James Hook & Co also serves up a great roll.
The Lower Depths Tap Room (476 Commonwealth Avenue) raises the bar for pub food. Try the build-your-own Fenway Franks, one of the crispy tater tot varieties, or the tasty nachos. For a more touristy spot, check out the original inspiration for the show “Cheers:” Cheers Bar (84 Beacon Street). The Union Oyster House (41 Union Street) is cool to check out since it’s Boston’s oldest restaurant, but stick to the chowder and corn bread. There’s not much else to rave about.
For the Sports Fan
If you’re a baseball fan and don’t have the chance to watch a baseball game live, you will want to get the next best experience by eating at Jerry Remy’s (1265 Boylston St). Owned by Mr. Red Sox Nation himself, Jerry Remy’s has upped the ante (and the cholesterol count) for Fenway bars. The TVs are mammoth, and the kitchen serves a burger wedged between two pieces of fried dough. Best of all, the bar room is so close to the park that when the windows are open, you can even join a “Yankees suck” chant while noshing on a tasty RemDawg sandwich. Yankee Lobster (300 Northern Ave, between C St & Trilling Way) is a 5 minute walk away and serves great chowder.
Bowl a few rounds and down a few buds at Kings Lanes (50 Dalton St). Complete with high-tech scorekeeping machines and several high-def TVs, it’s a fun place to unwind during the weekend. Though the crowds of stylish professionals and grad students can mean long lines for pool tables and lanes, they also make for a buzzing scene. Prepare to wait an hour.
Shopping
Look out for The Boston Shaker (69 Holland Street) if you enjoy mixing a mean drink.
Cheap Fun
Head to the New England Aquarium to see piranhas and eels of the Amazon as well as charismatic penguins for less than $25. The nearby Legal Sea Foods on Long Wharf certainly isn’t cheap, but serves excellent seafood. The Gardner Museum (280 Fenway) is one of the more unique and wonderful things to see in Boston. The Sports Museum, located at the TD Garden, is even cheaper at $10 and is a must-see for any sports fan.
The Havana Club in Central Square hosts beginner and intermediate salsa lessons on Friday and Saturday nights from 9 p.m.-10 p.m. (no partner required). Price of admission is $12 and includes lessons, the after-party, and coat check.
For cheap eats, Cactus Mexican Grill (44 Maverick Sq) is a great place to look out for. Food is always fresh, and serves up great tacos and burritos.
