This is my neighborhood and I love it dearly. Here are some reasons I've stayed in a 1 mile radius since I moved to the area:
Inman Square, Cambridge:
Easily accessible from Harvard Square or Central Square by public transportation or a pleasant 1 mile walk (north up Prospect St. from Central or east from Harvard Square up Cambridge St.). There are tons of great restaurants of all different cuisines: Seafood, Barbecue, Thai, Southern US, and Persian just to name a few. Christina's Ice Cream and Spice Shop (corner of Cambridge and Prospect Streets) are a highlight - crazy and amazing flavors. Bukowski's has a great selection of beer and a great windowed front wall that's fun to sit at and watch the world go by. There are a few vintage boutiques with used clothing and a variety of items made by local artists.
A few steps east down Cambridge St. brings you to East Cambridge, a great "neighborhoody" neighborhood. I come here to buy chicken and eggs from Mayflower Poultry Co (look for the "LIVE CHICKEN FRESH KILLED" sign). Even if you're not in the mood for raw meat, they have great T-Shirts. Atwoods is a great pub with a laid back atmosphere and great beer and food selection. Court House Seafood is the local fish store with restaurant attached - the best place around for affordable fresh seafood. There are also a number of Portugese and Brazilian restaurants along this strip, the best of which is MuQueCa. Amazing meat and seafood dishes and vegetarian friendly. The garlic rice alone is worth the trip.
This Boston site is very useful for tourists and visitors in general; it has lots photos and info about all the neighborhoods (even the least known ones) in Boston: http://bostonneighborhoods.blogspot.com/
If you are traveling by car, explore hotels in the suburbs around Rt. 128: Waltham is one of them. You may get much better deal and it is withing 20 min from downtown Boston.
Use Masspike off rush hour, between 9:30 am and 3:30 pm, it only takes 10 min to get to Faneuil Hall from intersection of Masspike/Rt. 128.
Newton is another suburb worth exploring in terms of accommodations. It is safe, prosperous, people are highly educated and comfortable with their lives. Green, has lots of possibilities for jogging. Go to Bridge street: right out of the bridge, there is a jogging path along the Charles river. Stop and watch swans, turtles, man-made waterfall, bike. Newton has 2 kayaking stations on the Charles river. One on a way to Cambridge has several huge-size FREE parking lots and beautiful playground just next to Charles. It is an easy ride along the famous Regatta path. You will pass Cambridge, go under a couple of old bridges, see people passing by on both sides of the river. Very relaxing and delightful way to see Boston and suburbs. Sorry, I only live there, so can't provide you with hotel tips.
Spend 3 hours on this walking tour learning about this ethnic neighborhood in Boston's North End. What I learned about balsamic vinegar was worth the ticket price. The tour includes tips on purchasing food and cooking and tastings of many specific Italian foods.
I discovered Davis Square on my first trip to Boston. Located in Somerville (Cambridge), there is a great Bed and Breakfast (See my tip on Morrison House) and evrything you need for a great vacation located within easy walking distance. In July, the Somerville Arts Council throws a big block party in Davis Square. You can pick up great bargains made by local artists. Paul Fata is always a hit. Davis is on the Red Line MBTA stop. Before leaving the station say hello to Sayid behind the counter. Get the Mango Juice Smoothie while you're there. The Square has it all. There's JP Licks for ice cream, Diesel Cafe for great salads and Raspberry Lime Rickeys, street musicians performing nightly, Jonny D's for food and great music, McIntyre and Moore for book browsing and more music. Check out the funky bargains at the local Goodwill store. Videos are $1.99, paperbacks are $.79 and this is Boston after all so you won't believe what you'll find in this place! The "locals" who shop here are a treat for the eyes and ears. They could all be extras in a John Waters movie! One of the best meat market/delis is also here; McKinnon's. Stop in for pic nic supplies (cheeeeeep is the word). Try the Hoods lemonade. I took home containers of the black olives and pepperoni I bought here. It was THAT good. The people who run this place are the nicest in Boston without a doubt, that's why folks come from all over Boston to shop here.
Boston and its surrounding towns have a lot of Squares. The Squares are not square in the geometry-sense of the word, rather they are areas where several streets intersect. Each Square has its own flavor.
The closest T station is indicated by its corresponding color. ie: Harvard is on the red line.
Copley Square : Copley
Kenmore Square : Kenmore
Post Office Square :
Dewey Square :
Harvard Square : Harvard Home of Harvard University- Massachusetts Avenue, Brattle Street, and John F. Kennedy Street.
Porter Square : Porter Massachusetts Avenue and Somerville Avenue, between Harvard and Davis Squares.
Kendall Square : Kendall Main Street, Broadway, Wadsworth Street, and Third Street
Central Square : Central Massachusetts Avenue, Prospect Street, and Western Avenue.
Inman Square : Cambridge, Hampshire, and Inman Streets
Lechmere Square : Lechmere located at the intersection of Cambridge St. and First St
Davis Square : Davis Holland Street, Dover Street, Elm Street, Highland Avenue, and College Avenue
Union Square : Washington Street and Somerville Avenue
Ball Square : Boston Avenue and Broadway
Teele Square : Broadway, Holland Street, and Curtis Avenue
Magoun Square : Broadway and Medford Street
Powderhouse Square :
Diverse Boston neighborhood , one of the poorest areas in Massachusetts.
The Dudley Square area is being built up. You can find a myriad of culturally diverse stores. It's a trilingual area, residents are mostly African American, Latino , and Cape Verdean.
I was fascinated by the historical significance of Beacon Hill. From the outside John Kerry's House is indistinguishable from the other uber fabulous residences in the area except of course for the secret service poised on the corner of Pinckney Street.
Jamaica Plain is fun little Boston neighborhood. It's got a mix of people from different Ethnicities, lifestyles and Income levels. You can stroll down Centre street and find funky arts and crafts stores, great Latin American Restaurants and Antique Stores. Or you can stroll up a side street and see many beautifully restored Victorian homes.
Boston's traditionally black neighbourhood.
Situated south of the South End, north and west of Dorchester, and east of Jamaica Plain.
T stops: Roxbury Crossing (Orange Line), Ruggles (Orange Line), Green Street (Orange Line), Dudley Square (Silver Line)
Bounded by Heath Street to the north, Arborway to the south, the Jamaicaway to the west, and the Northeast Corridor railway trench to the west.
T stops: Heath St. (Green Line E), Jackson Square (Orange Line), Forest Hills (Orange Line)
Many of the outlying suburbs are significant from an historical value. I spent a lot of time in Salem and Danvers areas, but at least a dozen towns have things to see and do
Located south of Jamaica Plain and Roxbury, north of West Roxbury, and west of Dorchester
T stops: Roslindale Village (Commuter Rail)