Brookline is located directly west of Boston proper. It is bordered on the south by Chestnut Hill, on the southeast by Jamaica Plain, on the east by the Fenway-Kenmore, Longwood and Mission Hill sections of Boston proper, on the north by the Boston University campus and the Charles River, and on the west by Allston and Brighton. Brookline was initially incorporated as a part of Boston proper, but has since seceded and gained its own identity as a western district of the Boston metropolis.
Brookline is served by Boston's major transportation terminals, including Logan International Airport
Brookline is served by three branches of the MBTA (the T) Green Line light rail.
Take the C line from Boston proper and get off at one of the main stops in Brookline. Coolidge Corner is a great place to get off the train.
The D line, also accessible from many places downtown, will bring you to the southern areas of Brookline — the Brookline Village, Brookline Hills and Beaconsfield stops. The areas around those three stops are great quaint areas with many restaurants, though they aren’t as big a draw for people who live outside the area.
The B Line flanks Commonwealth Ave., and its stops from Babcock Street to Boston University East serve the Boston University campus, the westernmost parts of Boston proper, and North Brookline.
The D line is much faster with less stops than the B and C lines. If given the choice between one or the other, take the D line.
All MBTA rapid tranist trains are now $2.90 per trip ($2.40 with a plastic "Charlie Card").
If you are disabled, think carefully before taking the train into Brookline. Only a few Green Line stops are wheelchair-accessible (the MBTA website should have the most current accessibility information). During busier times of day wheelchair users should have little difficulty getting to Coolidge Corner, Washington Square, and Brookline Village on one of the newer Green Line trolleys with low floors; however many older-style cars with large steps up are still in use, especially during non-peak hours, and these are accessible only via hand-cranked wheelchair lift. The situation is better now than it was even just a few years ago, but the Green Line is still a long way from being universally accessible. The other rail lines in the MBTA, for the most part, have handicap access.
Cars and Brookline, like most of Boston, do not mix perfectly. One thing to be aware of is that there is generally no overnight parking on streets; those cars on streets after 2AM (11PM in some areas) will be ticketed...seriously! There is also a two-hour parking limit, which is not as strictly enforced. (But wouldn't you know it, your car will be the one that gets ticketed :)
The following Massachusetts Bay Transportation Authority  bus routes are in Brookline:
Route 66-At Coolidge Corner and Brookline Village. Runs up and down Harvard Street and continues north to Allston and Harvard Square.
Route 65-Is less frequent, goes through Brookline Village and Washington Square and continues north to Brighton Center in Allston-Brighton.
Route 60-Goes Along Route 9 (Boylston Street) and Cypress Street. Goes through Brookline Village and other southern sections of Brookline, and also serves Chestnut Hill and Fenway-Kenmore. Continues west to Chestnut Hill Mall, and east to Kenmore Square.
Route 51-Goes from Cleveland Circle in Brighton into the western part of Brookline and continues into Chestnut Hill (the Hancock Village/Putterham areas) and on to the Forest Hills MBTA station in Roslindale.
Route 86-Goes from Cleveland Circle north into Brighton Center and Harvard Square.
Many buses that go to other cities including New York, stop at the Riverside MBTA Stop in Newton on the D Line. The train can be taken into Brookline.
Brookline has no navigable bodies of water along its borders. Therefore one cannot arrive in Brookline by boat. Theoretically one could cross the Muddy River by canoe or raft and in doing so travel from Boston proper to Brookline via boat, or one could take a boat on the Charles River to Boston University if they are staying in North Brookline... but that would be just plain silly.
Coolidge Corner - A shopping area with much to do. Is the most happening area in Brookline. On C Line, Coolidge Corner Stop.
Brookline Village - A somewhat sleepier historic area with many restaurants. On D Line, Brookline Village Stop.
Washington Square - Local shops and some popular restaurants and taverns. On C Line, Washington Square Stop.
Brookline Hills - Around the high school and across Route 9. Very residential. On the D Line, Brookline Hills stop.
Cleveland Circle - Actually in Allston-Brighton, but is right on the border with Brookline. Large student population, due to its proximity to Boston College. Has some bars, restaurants pizzerias, but is slightly more run-down than Brookline proper (although gentrifying). The intersection is very confusing, as it is the intersection of three different lines of the T, although this also makes this intersection convenient. Take the C Line outbound to the Cleveland Circle stop, the D Line to the Reservoir stop, or the B Line to the Chestnut Hill Ave stop.
St. Mary's- Overshadowed by nearby Kenmore Square and the Landmark Center in Boston proper. The area has a little bit to it. Is On C Line, St. Mary's Stop, On D Line, Fenway Stop.
Pill Hill/The Point - Residential area to the south of Route 9. Ritzy. From this area, one can either walk to the Brookline Hills or Brookline Village stops on the D Line, or take the Route 60 bus.
JFK Crossing - Stretch along Harvard St. with a heavy Jewish influence, from just north of Coolidge Corner to Commonwealth Ave. in Allston.
Boston University/North Brookline - Boston University’s sprawling campus is stretched along a 1.5 mile plot of land flanking Commonwealth Avenue and running through Brookline, Allston-Brighton and the westernmost part of Boston proper (although the BU/Comm Ave strip itself is pretty much entirely in Boston proper). There is a wide variety of shops and restaurants here, although they are largely student oriented. But if you’re looking for an authentic college town experience in Boston, this is where you’ll find it!
The primary way to get around in Brookline is to walk. Most places of interest are close together, or if you need to go farther away, a short ride on the MBTA will do it. If you choose to drive, be aware—especially on Beacon Street, where the trolley runs down the middle of the street. If one is required, cabs can be easily flagged down on the main streets, and are oftentimes parked curbside waiting for fares at busier hubs (e.g. Coolidge Corner, Brookline Village).
The Coolidge Corner Theatre, 290 Harvard Street, Phone: +1 617-734-2501, recorded info:, +1 617-734-2500, . A charming, old fashioned movie theatre that plays art house films, as well as some crowd-pleasers.
Brookline is home to some of the best public schools around. Brookline High School has many famous alumni including Theo Epstein, the former General Manager of the Boston Red Sox and current President of Baseball Operations for the Chicago Cubs; Michael Dukakis, former Massachusetts Governor and 1988 Democratic Presidential nominee; Robert Kraft, current Patriots and Revolution owner; Conan O'Brien, TV host.
Harvard St. between Commonwealth Ave. and Beacon St. is a heavily Jewish neighborhood: the majority of the kosher restaurants in the Greater Boston area can be found here. These restaurants are best accessed by the 66 bus, although they are within walking distance from the Harvard Ave. stop of the B branch of the Green Line and the Coolidge Corner stop of the C branch of the Green Line. Keep in mind that like most kosher restaurants, these restaurants are closed Friday night and only open late Saturday night (if at all on Saturday) due to the Jewish Sabbath.
In addition to the restaurants listed here, the J.P. Licks mentioned above is also kosher. 
Boston (and Massachusetts as a whole) uses 10-digit dialing. This means you need to include the area code whenever you are making a call. The standard area code is 617, but some phone numbers, especially cell phones, use the new 857 overlay.
Brookline is incredibly safe, with an impressive police presence. Pedestrians entering Brookline for the first time from some of rowdier sections of Boston that border it often speak of a noticeable change in atmosphere; there are fewer drunks and homeless people, more police, and the beer cans and cigarette butts that line the sidewalks of neighborhoods like Allston disappear. The cops works very hard to keep it this way and police can be aggressive. Police in Brookline will often annoy the local high school and college populations for "rowdiness."