12 Insider Tips to Consider Before Visiting Boston

Picture this: I’m meeting my future husband’s family in Boston for the first time. His mom asks if I’d like a tonic. It sounds a bit strange, but refreshing, so I say yes. She then brings me an orange soda. Wait, what?

You’ve probably figured out that tonic is the local term for soda in Boston – just one of many quirky regional expressions that still thrive in the local dialect. After nearly 25 years of living here, I think I've finally mastered them, along with a few other insights.

From navigating the city’s streets to understanding social dynamics, here are the essential tips and tricks to know before heading to Boston.

1. From April to October, make reservations in advance – for nearly everything

If you're visiting Boston during peak season, you'll soon realize you’re not alone. To secure a good selection of seats and ticket prices for events, purchase your theater or Red Sox (or any major sports event) tickets at least a month in advance.

It's wise to buy advance tickets for the most popular museums, particularly the New England Aquarium. Booking just a day or two in advance will ensure your entry and save you the trouble of waiting in line when you arrive.

If there's a specific restaurant you want to dine at, aim to book your table one to two weeks in advance, especially for weekend nights. Some of Boston's trendiest spots may require reservations several months ahead of time.

2. Avoid Driving in Boston

One thing you don’t need to reserve in advance is your rental car – because you won’t need one! Driving and parking in Boston can be quite the headache, so it's best to forgo the car. Make sure to bring comfortable walking shoes, as this compact city is best explored on foot.

3. Be Prepared for Any Weather

Boston’s weather has been perplexing meteorologists for years, and it can confuse your weather app as well. Conditions can change from day to day and even hour to hour. It’s wise to carry both an umbrella and sunglasses, as the weather is likely to shift while you're out and about.

Chilly temperatures can pop up at any time, even during summer, so don’t forget to pack a jacket for the evening – even if it feels warm during the day.

4. Bostonians Tend to Be Reserved

Bostonians typically do not greet strangers on the street or initiate conversations on public transport, so you might not receive a greeting or engage in conversation either. Don’t take this customary reserve personally. However, most locals are more than willing to help with directions or answer questions, so feel free to ask for assistance.

5. Familiarize Yourself with Local Lingo

Long-time residents of Boston have some unique ways of expressing themselves, especially regarding food and drinks. For instance, we refer to a ‘frappe’ instead of a milkshake, enjoy ‘honey-dipped’ donuts rather than glazed ones, and might ask for ‘jimmies’ on our ice cream instead of sprinkles. Unfortunately, many of these delightful regional terms are fading, but here are some key ones to know.

• Bostonians are big fans of Dunkies – our affectionate term for Dunkin’ (they dropped ‘Donuts’ and adopted the mononym in 2018). Dunkin’ locations are everywhere in Massachusetts, with 85 outlets in Boston alone.

• The city's central park is called the Boston Common. It holds the title of the oldest public park in the United States, and there’s only one. Please don’t refer to it as ‘the Commons’.

• When not walking, Bostonians use the T, short for MBTA (Massachusetts Bay Transportation Authority). All stations feature a prominent sign that says ‘T’. It’s not the subway or the metro – it’s the T.

6. Understand Your T Etiquette

Speaking of the T, it’s the preferred mode of transportation for everyone. It’s a convenient and easy way to navigate the city. However, the trains can get packed, particularly during rush hours, so it’s essential to be aware of local customs and manners.

• On escalators, stand on the right side and walk on the left.

• When the train arrives, step aside to let passengers disembark before boarding.

• Be sure to offer your seat to children, the elderly, pregnant women, and those with disabilities.

• You can chat among yourselves, but there’s no need to start a conversation with the person next to you.

7. Show Appreciation to Your Servers

In the US, it’s customary to tip restaurant staff and bartenders – not just because Americans are generous, but because many depend on these tips for their livelihoods. In fact, servers and bartenders earn much lower hourly wages based on the expectation that most of their income will come from customer tips. In Massachusetts, for example, the standard minimum wage is $15 per hour, but the tipped minimum wage is significantly lower at just $6.75 per hour.

Most restaurants don’t automatically add a service charge to your bill, except in specific situations like large parties. Therefore, it’s your responsibility as a customer to tip generously – 15% is the minimum, 20% for good service, and 25% for exceptional service.

8. The Boston Accent is Serious Business

If you’ve watched Good Will Hunting, you’re familiar with the Boston accent. (And if you haven’t seen it yet, you definitely should!) The accent features dropped r's after vowels ('smaht kids go to Hahvahd') and an added r sound at the end of vowel-ending words ('a slice of pizz-er').

While the Boston accent isn't as prevalent as it once was, it remains common, particularly in working-class neighborhoods. Like any accent, it’s best not to mock or imitate it. In fact, there’s really no need to comment on it at all.

And definitely avoid saying, ‘Pahk the cah in Hahvahd Yahd,’ especially since cars aren’t allowed in there.

9. Be Cautious When Discussing Politics and Sports

If you manage to break through that Yankee facade, you’ll find a warm, engaging community that is deeply passionate about politics and sports. Bostonians aren’t shy about sharing their opinions, which tend to lean liberal politically and fiercely loyal when it comes to their sports teams. If you disagree, just know that discussions might heat up.

And no, it’s not advisable to trash talk former New England Patriots quarterback Tom Brady.

10. Understand Boston’s Complex History with Race

Despite its progressive reputation, Boston has unfortunately long been seen as unfriendly, or even hostile, towards people of color, particularly Black individuals. Instances of harassment and racial slurs can be more common than one might expect in a city that prides itself on being progressive.

Boston is now classified as a ‘majority minority’ city, meaning that over half the population comprises ethnic, social, or racial minorities. However, both the city and its schools remain largely segregated, despite integration efforts dating back to the 1970s. Moreover, the power structures were predominantly controlled by white men until recently; it was only in 2021 that Michelle Wu made history as the first woman and first person of color elected as Boston’s mayor.

11. Don’t get burned for getting high

Cannabis is allowed for recreational purposes in Massachusetts, and dispensaries are popping up throughout Boston. However, there are numerous regulations to follow, so make sure you understand the laws before partaking.

Adults aged 21 and older can legally buy and possess up to one ounce of marijuana (or 5 grams of marijuana concentrate). However, using marijuana in any public area is prohibited. Parks, beaches, and sidewalks are all off-limits, and social consumption venues like cannabis cafes are not yet available. Like alcohol, driving while under the influence is illegal.

Cigarettes and tobacco products are permitted for adults aged 21 and older. However, they are banned in workplaces, which includes restaurants, bars, hotels, and public transportation like taxis. Smoking and vaping are also prohibited in all Boston parks and beaches, with the only exception being designated smoking bars that have a special license.

12. Know who to contact for assistance

Dial 911 for emergencies. For information on city services or to report a non-emergency issue in Boston, call 311.