1. Boston’s a small big city. If you didn’t know any better, you’d think its got masses of people because of its name recognition and reputation, but it’s actually on the small side. The city itself only has a little over 600,000 people in it, but the Metropolitan area spreads out rather far and gets the number up to 4.5 million. The good thing about the city itself being on the small side is that it’s very easy to walk around compared to some other major cities. Part of the draw for the younger crowd is that something like 1 in every 5 people in Boston is a college student and there’s a large population of people who stay there after college. Young crowds bring a good weekend scene, whether you’re looking for outdoor day drinking or the regular nighttime activities. There’s lots of different areas to have fun in, so you can put together quite the long weekend there. As someone who went to college there, I can tell you there’s plenty of ways to get yourself into trouble. There’s going to be a lot to digest in the next nine points, but just absorb what you can.
2. Since it’s a major city, Boston is vibrant during most times of year, but I’d avoid the dead of winter if you can. It gets pretty cold during the winter and Boston’s got a bit of a line problem for the good bars, so waiting outside in the cold blows. Snow storms shut the city down and are prevalent at least two or three times a winter. The best time to visit is probably in mid to late spring when the Red Sox are in full swing or in the fall. The summer’s not bad either because it doesn’t get as warm as big city options that are further south, while still offering plenty to do. Patriots Day is one of the most fun days in the city because a lot of people have off work, the Red Sox play a game at 11 a.m. and Boston Marathon takes over the city streets. Here’s hoping it has a great bounce back performance next year.
3. Apartment or house rentals are likely a no-go for this one since it doesn’t necessarily make any sense. The neighborhoods you should be looking to stay near are either Government Center / Downtown, Boston Commons, Back Bay, or Copley. Boston has a late night cab problem and worst case scenario you need to be able to walk home if you have to. Anything further west or south makes it slightly harder for you to get around. Fenway, South End, and Seaport aren’t great for public transportation. I also prefer not to stay in Cambridge because getting back there can sometimes be a pain after the bars. You can basically just hit Priceline for a hotel because most places you’ll end up staying are fine. I’ve stayed at many a hotel in town and can throw out the following names from my Priceline history: Boston Park Plaza (usually cheap & good location), Courtyard (same characteristics as the Boston Park Plaza), and the Omni Parker House (good location, slightly more expensive). Places to avoid would be the Copley Square Hotel (rooms too small) and Hotel 140 (walls are way too damn thin). Stay at the Liberty Hotel if you wanna throw down some real cash. It’s a former prison so it’s got a cool vibe and they’ve got two good bars that attract a scene.
4. Boston is obviously a sports town with four major sports teams who have won a few championships in the last 15 years. Boston’s a baseball town first and foremost, which is why you should make sure you can get to a game at Fenway Park. It’s old and a lot of the seats don’t face home plate directly, but it’s always a fun atmosphere for a ballgame. The Monster seats are cool, but I almost prefer the standing area in the Budweiser Deck in right field. The cheap bleacher seats are always a fun time too if you have a large group and aren’t looking to spend money. If you don’t want to spend big money to get up to the Monster during a game, then take the Fenway Park tour so you can at least see what it’s like up there even if a game isn’t going on. Next up on the sports list would be a Bruins game. They’ve put a very competitive team on the ice over the last three years and hockey is as strong as it’s ever been in town. Celtics games are decent too, but the fan base isn’t as rabid. (There are plenty of good bars near the TD Garden to get your pregame drink on.) Finally there’s the Patriots, but I wouldn’t make a trip out to Foxboro unless you were really dying to. It’s not the easiest to get to and isn’t anything special as far as a venue goes. The wild card for Boston sports is the college hockey scene. Boston University and Boston College have a huge rivalry, so a game between the two is a sneaky good option. There’s also the Beanpot every February, which is a tournament pitting the two aforementioned schools against Northeastern and Harvard and takes place at the TD Garden.
5 – Boston is a beer town, which is why it makes sense that there are two good breweries in town that offer tours. You won’t go wrong whether you pick the Samuel Adams or Harpoon tour. The Samuel Adams tour is a little more out of the way, but you can pick up a Zipcar to get you if a taxi is too much of an issue. You get an hour tour, which ends with everyone’s favorite part, a tasting of multiple types of their beer. Harpoon has less brand name recognition than Samuel Adams does, but its brewery is much more convenient for a tour. They just redid the place and it’s awesome now. Of course you get to sample the beer here as well. Both tours are pretty cheap, but just make sure to check out the schedules and get there earlier in the day because lines for both can be a pain during busy seasons.
6. As you’d expect out of a major city, the food options come fast and furious in Boston. There are plenty of good burgers to sample in town and that has nothing to do with the fact that a Five Guys and a Five Napkin Burger recently opened in these parts. There’s much debate about where to get the best burger, but two choices come in the South End at Coda and secondly the Butcher’s Shop. Coda is the cheaper of the two options, but the TBS Burger at the Butcher’s Shop is worth the price. (Any burger with a brioche bun automatically goes up a couple points.) Locals also talk about classing it up a little bit with the burgers at the bar of Radius and in the lobby of the Four Seasons hotel. While the burger debate rages on, the best pizza in town is without question at Regina’s in the North End. I highly advise going during off-peak times because the lines outside during prime hours can get up to an hour long. The pizza here can at least compete with the other Northeast area legends of New Haven and Brooklyn. Don’t fall for the gimmick of getting the quick-service Regina’s outposts in Fanieul Hall or South Station because it’s not the same thing. (Also if you’re near the Boston University campus for some reason, head on over to T Anthony. It’s a local favorite of students and was the closest thing to a New York slice as I found on campus.) While you’re making your way around the North End, stop off at Mike’s Pastry for one of their legendary cannolis. Some people call it a tourist trap and prefer Modern or Maria’s, but I guess I’m a sucker for the tradition.
7. The hit list on food just keeps coming. Now that we’ve got the favorite food categories of burgers and pizza out of the way, why not grab yourself a burrito? Anna’s Taqueria makes the best burrito around Boston and has locations downtown, in Cambridge, and in Brookline. You can also grab good general Mexican food at Papagayo, where the guacamole and ceviche should be on the top of your list of things to order. Obviously you’re expecting some seafood while you’re in the northeast and there’s plenty of that too. Get a lobster roll at B&G Oysters, clam chowder (and plenty of other things) at the Chart House, and oysters at Island Creek Oysters or Neptune Oyster. Boston’s got their own Chinatown with many options, but my staple was always Moon Villa. Basho in the Fenway area gets you a Japanese fix. Sweet Cheeks is in the same area and gives you the closest thing to authentic barbecue as you’ll find in these parts. Your options get rather scarce when you’re looking for late night food. Your three best options are the rice balls at Café Pompeii, any Chinese food you can find in Chinatown, and the food you’d expect to enjoy at South Street Diner. Mike & Patty’s provides a nice hangover cure with the Bacon & Egg Fancy as the order of choice at this casual brunch takeout option.
8. As mentioned before, there are plenty of different areas in town to have your drinking fun. This all might be too much to take in, but we’ll give it a shot. In no particular order, we’ll start down at the Seaport because that’s the area of town that has exploded in the last few years. Atlantic Beer Garden (The Beer Garden family has multiple locations in the Boston area) and Whiskey Priest are where most of the action has been for the younger crowds over the last two years, but you need to get there soon because they’re closing those two places down for a massive new construction project soon. Both have roof decks and ABG has a little more of a dancing thing at night. The roof at Legal Sea Food has become a thing, Jerry Remy’s Sports Bar is always crowded, and you can hook yourself a cougar at the bar of Del Frisco’s Steakhouse. Lucky’s Lounge isn’t along the water, but is also a local favorite for, as you would expect it, more of a lounge feel. In not too far South Boston, there’s a massive group of under 30s who hang out at a regular basis at new spot Lincoln (for the late 20s crowd), which has good food and gets good at night, as well as old favorites like Stats Sports Bar and the Boston Beer Garden. (See, I told you there were more Beer Gardens.) Heading back towards downtown, you can enjoy a pretty wild day drinking scene at Tia’s or the Landing in Boston Harbor / Waterfront area. The bars in and around Fanieul Hall were huge a while back and aren’t as big now, but things can get pretty grimey at places like Jose McIntyres and Bell in Hand. There are a few places close to the TD Garden that get busy on weekends too, notably The Harp & West End Johnnies being the two busiest.
9. Boston’s not necessarily a fancy place when it comes to its bars, so it should be no surprise that there are many a good sports bar in town. My favorite is Champions in the Marriott hotel in the Copley area because you can sit at or near the bar and enjoy at least 10 TVs at once (great for football Saturdays and Sundays). The nachos have always been really good even if the wings aren’t what they used to be since the remodeling. The Samual Adams cheese dip is tremendous, however, and the sampler tower is sure to keep you busy. Game On! near Fenway is a good pre and post-game option for a Red Sox game, but also offers good enough food and plenty of TVs regardless of season. Stats and Jerry Remy’s, both previously mentioned, fill this void as well. Back to nighttime activities, the slightly older crowd should be checking out places like The Brahmin (you’ll like this place if you’re a New Yorker) and The Bee Hive in the South End for their weekend pickup activities. The younger crowd might want to move around the edge of Boston University’s campus to check out Tavern in the Square (there are a few of these located around the area) and White Horse Tavern. (Yes, there are a lot of taverns in Boston.) There’s also a load of bars in and around Boylston Street, but I never enjoyed them as much as other places in town. Places like Daisy Buchanan’s, LIR, Dillon’s, and the Pour House always get a lot of love. Finally there's Clery's in Back Bay where the basement really heats up around midnite. I’m sure I’ve just listed enough bars over the last two bullet points to get you through your time there, but there are obviously plenty of others.
10. I spent a fun four years in Boston during my college days and I visit Boston regularly, so I don’t want what I’m about to say to be put too much of a negative spin on things. There are certain elements of hanging out in Boston that you need to be aware of and you can deal with them just fine as long as you’re prepared. As mentioned briefly earlier, lines become an issue in this city. Things get a little ridiculous, especially near the TD Garden and in the Seaport area when it comes to getting in places. The Seaport area even has lines as early as 8 p.m. on Fridays and Saturdays, so get started early. Secondly, the late night cab situation (as also previously mentioned) is horrific. If you leave a bar at 2 a.m. when they close, be prepared to wait a long time to get a cab home. The waits could be very long and you may have to walk home (or at least to hotels where you can cabs periodically – secret of the pros) and they get worse in bad weather. When I say the city shuts down at 2 a.m., I mean it fucking shuts down. You can’t even take the T (aka subway) because that stops at 12:30 a.m. These last two points should encourage you to start early and finish early. (Maybe it’s my New York mentality, but this took me a while to get used to.) You’ll still have plenty of fun.
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