10 Mistakes People Make When Visiting Boston

Driving in Boston is notoriously difficult, so if you’re not entirely confident in your skills as a driver – especially in new environments – stick to using public transportation, taxis or your favourite rideshare service.

What makes it so bad? Well, in addition to Boston being a major city and having all the traffic that comes with a large population, the street system isn’t that newbie-friendly. While destinations such as New York City work on an easy-to-understand grid system, you won’t find that here. Additionally, because so many people in the city centre have learnt that walking is one of the better ways to get around, you’ll be dealing with a lot of pedestrians. Skip the rental car and join them.

So, you think you’re prepared to deal with a little winter weather? Don’t mind the cold and ice that much? You haven’t experienced a Boston winter. If you plan on visiting this city from November through March, make sure to pack your winter coat, hat, gloves, a few extra layers, snow boots, and all the rest. You’ll definitely need them.

Typically, winter temperatures hover around the low 20°F to mid-30°F level. Boston is no stranger to extreme winter conditions, so keep that in mind when planning your trip. It may be delayed or cancelled in the event of a snowstorm.

We get it. The Boston accent just seems fun. But don’t go around asking Bostonians to “pahk the cah in Hahvahd Yahd”. You wouldn’t be the first and you certainly wouldn’t be the last, but these jokes and imitations aren’t exactly welcomed by the locals, which is understandable.

Just about every traveller has their own accent. Would you like it if someone came up to you and asked you to repeat something in “that funny way you talk”? Probably not. So, keep any imitations to the confines of your hotel room.

It might not seem like a big deal to you – they’re just sports teams, after all – but believe us when we say that Bostonians are serious about their sport. As such, they’re serious about their sports rivalries. This means, if you're travelling around Boston, you don’t want to wear attire branded with the logos or names of Boston’s biggest rivals.

It’s best to avoid the uniforms of all the major New York sports teams, such as the New York Yankees and New York Jets. You’ll also want to steer clear of rivals like the Los Angeles Lakers and Montreal Canadiens. In fact, just opt for Boston sports teams’ apparel or no sports teams at all. It’ll save you from some nasty looks and even some heckling.

During baseball season, a visit to Boston’s iconic Fenway Park for a Boston Red Sox game is one of the top tourist activities, even for those who don’t care for baseball. There’s just something about the historic atmosphere, the thrill of the game and the combination of a ballpark hot dog and cold beer in a plastic cup. However, a simple minor error could ruin the experience.

One of the biggest mistakes you can make when buying your tickets is picking the wrong seats. A lot of the seats aren’t up to today’s standards. You might be dealing with obstructed views, smaller-than-normal seats or seats that are completely out in the sun. For your best bet, purchase seats in Field Boxes 21 through 76.

If you love hitting up the bar scene when you travel, make sure you plan to start drinking early in Boston. While you can easily find bars that stay open until the very early hours of morning (or that don’t close at all) in many destinations across the world, you won’t find them in Boston.

Most bars, restaurants and other nightlife venues close around midnight or 1 am. This is partially due to liquor licensing laws that prevent businesses from serving alcohol after a certain time. 

Lots of cities have their little quirky statue traditions, most of them requiring you to rub the statue for good luck – Boston is no different. It’s popular for tourists to rub the foot of the John Harvard statue at Harvard University for good luck. In fact, the statue’s shoe is so worn by all this rubbing over time that it’s turned an entirely different colour than the rest of the sculpture.

However, you may want to refrain from putting your hand on John Harvard’s shoe and taking that photo. Harvard students think it’s great fun to pee on the statue’s foot, knowing that an unfortunate tourist will soon come along and find an unwelcome surprise.

Cape Cod is an absolutely lovely little summer destination about 60 miles south of Boston. The quaint New England seaside town attracts travellers from all over the world, plus its fair share of Bostonians. However, if you’re visiting Boston in the peak summer months, you’ll want to make other plans than hopping over to the beach for an afternoon.

Summertime on the Cape is crowded, crowded, crowded – and it’s not just the beach crowds that you’ll need to battle. You’ll also have to fight the traffic going to and from the Cape, which can make the 60-mile journey take hours and hours of your valuable travel time.

Boston sits right at the end of a line of some of the USA’s most popular cities and travel destinations, starting with Washington DC and going to Philadelphia, then New York and then Boston. But just because Boston looks close to these other cities on a map, don’t make the mistake of thinking that you can take an easy day trip to even the closest. That ‘quick’ drive to New York City can actually take at least 4 hours of driving per way.

If you really want to see some of these other cities, consider a side trip before or after your Boston visit. And if you plan on going all the way to Washington DC, consider flying.

Boston is quite walkable if you stay in the right area. Booking a hotel in Boston’s city centre will save you from walking endless blocks to get to and from your destination. It will also save you some travel cash as you pay for fewer taxis and rideshares.

When booking your hotel, look for properties in Downtown Boston, where you’ll find a bevvy of historic sites, shopping, dining, pubs, cultural attractions and more, all in 1 compact neighbourhood.