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224 Boston Street in Dorchester is a charming restaurant with a small outdoor terrace. Few people venture to this area, but the food and atmosphere is worth it.
Delux Cafe in the Back Bay (100 Chandler Street) is a small and funky neighborhood restaurant/bar that few people ever notice. It features walls covered in record covers, art by local artists, a small shrine to Elvis, and perpetual Christmas lights along with a tv that’s always on the Cartoon Network. With a handful of tables, no attitude, and a perfectly casual atmosphere, Delux is the perfect antidote to the yuppy restaurants in the South End.
Silvertone Restaurant & Bar on Bromfield Street downtown is a place not often frequented by tourists due to its somewhat hidden location. The menu consists of comfort food ranging from shepherd's pie to spaghetti bolognese at a price that can't be beat. And the overly tall booths make the place feel private even when it is crowded.
South Boston is traditionally known as an Irish neighborhood, but surprisingly enough they have a great Mexican restaurant. Check out Salsa’s Mexican Grill (118 Dorchester Street) for some authentic Mexican food. The chicken chimichanga is killer!
Casa Romero Located in an alley off of Gloucester Street in Back Bay, Casa Romero boasts a menu of authentic Mexican food in a charming setting. For those of you looking for cheap, TexMex fare, this is not the place for you. However, if you want a unique hidden location with wonderful sangria and a classic Mexican menu, venture into this hidden gem located in the heart of Back Bay.
Sam Adams Brewery - 30 Germania Street, Boston (Jamaica Plain neighborhood), MA 02130. For a true Boston experience, come to where Sam Adams is brewed. Offers tours and samples of their brew Thurs-Sat with $2 donation to benefit local charities. Accessible by Orange Line.
Harpoon Brewery - 306 Northern Avenue, Boston, MA 02210 (down by the harbor, very close to the airport by car). Another local brewery, despite its location inside an industrial park area, the brewery is worth the trip. Complimentary tastings are offered in a very classy 'tasting room' which is a combination bar/gift shop. Serviced by the Silver Line, or easiest by car (free parking lot). You can also purchase Harpoon 6-packs very cheaply there.
The Omni Parker House is one of Boston's oldest hotels and integrally intertwined into its local history. JFK made his first speech, announced his candidacy for President, and proposed to Jackie here. Ho Chi Minh and Malcolm X both worked in the hotel restaurant. The Boston Cream pie was invented here.
Kellys Roast Beef A train ride away, this is a must for when you are in Boston. At 410 Revere Boulevard at Revere Beach. Although they have seafood too, the roast beef sandwich is what it is famous for. You have to eat it with two hands holding it together as the roast beef is piled so high. Try the onion strings, too. You can eat your meal overlooking the ocean. Great atmosphere!!
The Tavern on the Water (Charlestown) - Located in the Navy Yard of Charlestown, Tavern on the Water is a great spot to get lunch/dinner if you happen to go see the USS Constitution and it's even worth the walk itself. You get an awesome view of the Boston skyline - including the Zakim Bridge (very pretty at night when it's lit up). Plus the food is delicious upscale pub grub, the beers are cold and if the weather is nice you can even eat outside!
If you find yourself in the West Medford area, perhaps visiting Tufts, Bistro 5 on Playstead Road is a great restaurant that can stand up to some of the finest restaurants in downtown Boston. The Zagat guide rates it among the top Boston area restaurants for food, but prices, although not cheap, are more reasonable than those of downtown restaurants. The decor is sophisticated and the service good. It would be a great place to take your starving Tufts student for a nice dinner. If you are inclined to make a special trip to Bistro 5, it is one stop (12 minutes) from North Station via the Lowell commuter rail line, and located directly across the street from the West Medford commuter rail stop. However, you will have to time your visit carefully as commuter rail service can be infrequent outside of weekday rush hours.
If you have a car take the Mass. Ave (don’t call it "Massachusetts Ave.") Bridge into Cambridge, turn right and park along Memorial Drive for a great view of the Boston skyline. You also have a great view crossing the Charles River on the Bridge, and go up a bit on Memorial Drive and see the Golden Dome of the State House and Beacon Hill. Especially unique and beautiful as the sun is setting!