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You’re going to want to read this before visiting Boston… especially if you like advice from a local.
So you’re taking a trip to Boston? Here are the things that you need to know before visiting.
From where to stay, how to get around, best time to visit and can’t miss things to do. There are also some very important things to know at the end, so make sure you check those out too!
Why Boston?
One of the oldest cities in America certainly has a lot of interest from tourists and residents alike, so it’s no surprise that you’re interested in spending time in this beautiful place. After living in this area for over 5 years, I learned a lot about the dos and don’ts of Boston.
Boston can be super confusing, especially for someone who hasn’t spent much time there, but don’t worry! If I figured it out, so can you… plus you have me to help you ;)!
Where should I stay?
While central Boston isn’t that big, there are actually a lot of good places to stay in the area, but you’re going to want to be near a T line so that you can get into the city. If you stay in central Boston, then it’s much easier to use the train since all lines lead to the center.
Since I spend a lot of time in Boston, I made sure to share where to stay in Boston. I share my favorite budget-friendly choices below… but if you want a comfortable stay, or learn about the best neighborhoods, make sure you check out where to stay in Boston here.
One option that a lot of people wouldn’t normally consider is housesitting. If you have semi-flexible travel dates and love animals (especially cats and dogs), using Trusted Housesitters is an affordable hack to stay in Boston.
Boston has a lot of people looking to watch their pets, but sits book quickly, so flexibility is super important. I’ve used this platform myself and highly recommend it if affordable accommodation is a priority.
If you aren’t much of a pet person or want much more flexibility on your time frame and what you can do in the city, there is plenty of other accommodation available.
Just keep in mind that the most affordable and well-located places book up fast. If you find something that fits your budget and your travel dates, I strongly recommend booking it right away.
If you want a SUPER affordable option, HI Boston is a great choice and it’s very central in the city, so it’s close to the lines and easy to navigate. It’s also one of the cheapest choices in the city for a bed, but keep in mind it’s a hostel.
If you have a bit more of a budget or a group for a private room, I’d highly recommend the Revolution Hotel in Back Bay. It’s affordable (for Boston), central, and it’s a cute little place with tons of room options.
My friends and I stayed in a hostel-styled private room, which was really interesting (pictured), but they have other options available that are more typical for hotel rooms.
Do I need a car?
While you can get around without a car, having one does give you a lot more flexibility… and parking isn’t as difficult as you think. Spothero is my go-to for affordable parking in the city.
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Keep in mind, Boston roads are not on a grid since they were made when cars were not yet invented, only horse-drawn carriages. As a result, the streets can be a bit tricky.
Just so you have both sides of the story, the MBTA (also known as the T to Bostonians) is super unreliable. It was the first subway system in America (dating back over 120 years).
Some say that’s the last time it was updated though, which is why it’s so awful. There aren’t very many lines, but the subway is insanely slow (I’ve seen bikers pass it).
If you aren’t staying right by a T station or just want to maximize your time in the city, you should rent a car. If you are planning to leave the city, you’re definitely going to want to rent a car.
The best platform I’ve used for renting a car in Boston is Discover Cars. They are more of a search engine for rental cars, so you can pick from tons of different companies and see which one gives you a better deal.
The convenience of having a car in the city is unmatched, especially if you’re planning any late nights or want to see the best areas near Boston only a 30 minute drive away!
Best time of year to visit?
Fall and spring are when Boston is the most beloved with all the changing colors (whether it’s flowers or leaves) in the historic streets.
Many people opt to visit Salem, which is a beautiful town with lots of Witch history in Massachusetts. You can reach Salem by boat or train from Boston, and it makes a great day trip.
Make sure to dress warm if you’re visiting in Autumn (September – November), since it gets a bit chilly in Boston. It’s a little less busy than summertime too, so that’s a good reason to visit at this time as well.
Checklist of important info
Boston is OLD, there is so much history as one of the oldest American cities.
It’s easy to get caught up in Boston’s food and drinking culture, and while it’s definitely worth enjoying, make sure you save time for other things. Some of my absolute must-dos are experiences like Whale Watching Tours and Boston Harbor Cruises. They give you a really unique perspective of the city.
Also, if you have any interest in history at all, taking a guided tour is so worth it. Boston is one of the oldest cities in the U.S., and having the context behind what you’re seeing makes it so much cooler. Walking tours and historic experiences bring the city to life in a way that wandering alone just doesn’t.
If you’re trying to visit Boston on a budget, don’t forget to check out my article on how to visit Boston affordably. I break down costs, savings tips, and realistic ways to experience the city without overspending.
What else to know before you go
Expect to spend a lot of time walking if you don’t rent a car because the public transit is not ideal.
Boston doesn’t have a happy hour! It was banned in Massachusetts years and years ago.
Get a 7 day unlimited past or a reloadable CharlieCard OR officially you can use a tap card on the MBTA services.
Boston has more than 138,000 students, so it’s a huge university city.
Make sure you try seafood, lobster is always the best and oysters are huge there too. Legal Seafoodsis the classic spot.
There is a ton of free stuff to do in the city, and it’s easy to find.
Boston isn’t open that late, the latest bars close around 1, MAYBE 2am at the latest. There are very very few places open late.
Final thoughts
If you’re planning a trip to this incredible city, make sure you plan accordingly since it can get a bit confusing at times. Even so, it is always worth it, and it offers some of the most beautiful views, especially along the Esplanade.
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