Before jumping into this Boston travel guide, I have good news and bad news.

The good news is: Boston is a really rad city these days. The bad news is: no one really talks with a Boston accent like Matt Damon or Ben Affleck from Good Will Hunting anymore.

Whether you’re greeted with a “good morning!” or a “good mawnin!” Boston is still one of the best cities in America.

Aside from being stunning, Boston is jam-packed with historical sites, great food, and unabashed character. For visitors and residents alike, there are so many things to do and see here that having the best Boston city travel guide pays off dividends.

I’ve taken all of my insider knowledge of the city and poured it into this one travel guide so that you can have a grand ol’ time in Boston.

You’ll soon know all about the best cheap things to do in Boston, where to stay on a budget, sample Boston itineraries, and the best places to drink.

Basically–you’ll be ready to hit the streets of Boston and explore them as the locals do. So what are you waitin’ for? Let’s get to it people!

We’re headin’ to Beantown…

Good mawnin’ Boston!

Why Visit Boston?

Boston is one of the coolest cities to add to your USA backpacking itinerary. It’s a charming place that’s easily digestible, idyllic in summers, and – best of all – it truly has something for everyone.

Take a trip back in time.

From its serene harbor and many historical locales to some of America’s most iconic sports teams, Boston is a place for backpackers, families, and anyone and everyone in between. Bostonians love their city, and as it’s home to just over 600,000 people, it has a small-town charm amidst the high-rises and luxury condos.

Boston can also transport you back hundreds of years into the past if you let it: old graveyards, the oldest park in the United States, and a whole lot more. And I can’t even talk about Boston travel without mentioning Fenway Stadium which has been open for ballgames since 1912.

Add in some of the best universities in the world (big up Boston, MIT & Harvard University!), New England seafood, and pedestrian-friendly streets and you have yourself one heck of a small city!

Plus, it’s the only place in the US where you can experience the unique version of English known as the Boston accent.

What are the Major Attractions in Boston?

Boston is one of the most historical places to visit in the USA, so it’s no surprise that a few of the city’s top attractions are related to its past. Additionally, Boston is a major sports and foodie destination: you certainly won’t go hungry during your visit. The city’s nickname is even derived from some food: Boston baked beans.

Follow me to Boston Public Garden!

As much as I recommend taking some time to simply wander around and see where you end up, there are a few Boston attractions that you just can’t miss:

  1. The Freedom Trail
  2. Fenway Park
  3. Quincy Market
  4. Boston Public Garden
  5. Cambridge

How Long to Spend in Boston?

As aforementioned, Boston ain’t big. It might not be the smallest city in the US, but it’s far from the largest. That means you can hit all the main sights relatively quickly!

3 days is the ideal amount of time to spend in the city, which would make for a nice weekend in Boston, though weekdays tend to be less busy for most of the year.

What is the One Item Every Traveller NEEDS???

There is one item every traveller NEEDS. Some travellers don’t even know they need it, but those travellers need it more than anyone.

What is this forgotten essential of the backpacker-life? SPOILERS! Guess you’ll just have to click the button to find out. 😉

Find Out What It Is!

A Sample 3-Day Itinerary for Boston

The following is a sample 3-day Boston itinerary. Don’t worry, we’re gonna cover most of the top destinations that were already mentioned in this travel guide, as well as some of the other best places to visit in Boston.

Day 1 in Boston: All About Downtown

Day 1 in Boston
1.Fenway Park, 2.Copley Square, 3.Boston Commons, 4.Beacon Hill, 5.North End

Make sure you have a comfortable pair of shoes because we’re kicking off this Boston itinerary with a long day!

Start by catching the T all the way to Fenway Park, which is one of the most famous stadiums in the USA. (Bostonians treat it like a church.) Baseball rallies are held here regularly and most of the bars are packed, regardless of whether there’s a game in progress or not.

Let’s depart from Fenway and head deeper into Downtown. Cross the Back Bay Fens and Fenway Garden Society and or Boylston Street, which is one of the city’s main roadways.

Walk about 20 minutes through the Back Bay district until you reach one of my favorite spots: Copley Square. This square hosts some of the most arresting buildings in Boston, including the Public Library, Trinity Church, and John Hancock Tower, all of which create a wonderful juxtaposition.

Continue walking east and soon you’ll arrive at the Boston Commons – the largest and most important park in the city. The Commons is a very popular place to hang out in, no matter what time of the year. Going for a swan boat ride is somewhat customary in the Commons, if not a little touristy.

Just north of the Commons is Beacon Hill, which is one of the most historically significant areas in Boston. Lined with brownstones, paved with cobblestones, and topped by the magnificent State House, Beacon Hill is like a time capsule from Colonial days.

Let’s wrap up our day and make a beeline for North End for dinner. The North End is the old Italian quarter and is one of the coolest places to eat in Boston. Here, the pasta is piled high, the meatballs are fat, and the bakeries are just about endless. Thanks, Italy.

Day 2 in Boston: Visiting Cambridge

Day 2 in Boston
1.Harvard, 2.MIT, 3.Charles River (near MIT), 4.Kendall Square Roof Garden

Though not technically a part of Boston, nearby Cambridge is still totally worth checking out thanks to its prestigious institutions. Most notably, Cambridge hosts two of the most famous universities in the world – MIT and Harvard University.

Let’s begin the second day of our Boston travel guide at the famed Harvard University.

If you grabbed the T, the first place that you’ll see on campus is Harvard Yard. The Yard is the oldest part of the campus and has been the setting for many films. The Yard is a bucolic setting and will probably be overrun by scampering students.

As you wander around the campus, you’ll notice that the architecture of Harvard is a gorgeous blend of several styles – Gothic, Classical, Revival – yet every building is still made from that quintessential red brick. Several of these buildings host noteworthy museums that are open to the public. For me, a tour of the campus is reason enough to visit Cambridge.

Let’s depart Harvard and visit a very different college: MIT (Massachusetts Institute of Technology).

Whereas Harvard excels in the fine arts and business, MIT is all about engineering and the sciences. MIT’s most notable building is the Great Dome – a fine example of neoclassicism. Aside from this triumphant building, there are lots of ultra-modern buildings on the MIT campus and these make for great foils to Harvard’s more traditional styles.

As you leave MIT, you will be greeted by the Charles River and the Boston skyline in the distance. This shoreline has one of the best views of the city and is a great place to catch the sunset.

If you’d like a nice quiet place to reminisce about the day, head to nearby Kendall Square Roof Garden, which is one of the best secret places in Boston and will reopen with its new sexier-than-ever design in Summer 2022.

Day 3 in Boston: South and East Boston

Day 3 in Boston
1.South Boston, 2.Seaport District, 3.Chinatown, 4.Long Wharf, 5.East Boston, 6.Lo Presti Park

On the final day of this Boston travel itinerary, you’re going to explore the edges of the city.

Let’s start in South Boston – home of Irish haunts and all things “wicked”. South Boston had a bad rap for a lot of years, being the headquarters for much of the city’s organized crime, but it has really cleaned up its act.

South Boston AKA “Southie” is now one of the most desirable areas of the city.

The most noticeable trait of South Boston is the Southie Boston accent, which has served as the inspiration for just about every bad Boston impression. While the accent isn’t as strong these days, hearing some old Southie ask for a “qua-ffee regula” from Dunkin Donuts might really make your day. Eavesdrop on some local banter before the accent disappears altogether.

Next, head up to the Seaport District, which is basically South Boston’s waterfront. This district is undergoing a huge renaissance and is home to many of the city’s best museums. Here you’ll find excellent institutions like the Children’s Museum, Institute of Contemporary Art, and the Tea Party Museum.

To wrap up South Boston, head across the channel and back into the Downtown area. You’ll first run into Chinatown/Leather District but head north to eventually arrive at the Long Wharf.

Long Wharf is home to many of the city’s most well-known attractions, particularly Quincy Market, where you can grab a delicious meal on the cheap.

From the wharf, you can catch a water taxi to East Boston and then walk to Lo Presti Park. With unbeatable views of the city and plenty of athletic facilities, there are few better things to do at night in Boston than hang out here.

Spending More Time in Boston?

Got more time on your hands? There are plenty more things to do in and around Boston to keep you busy for way more than a weekend! Here are some of the more offbeat adventures the city has to offer:

boston harbor sunset with boats on water
Boston Harbor sunset: best free thing to do!
  • Chill at Corey Hill Park: Another stellar park in Boston that’s often skipped by tourists is Corey Hill, which actually sits over 260 feet above sea level. The park is over 4 acres, and has great spots for relaxing, exercising, or picknicking.
  • See a show at Symphony Hall: Constructed at the turn of the 20th century, this is regarded as one of the top three concert halls in the world. Many people plan their trips to Boston around the shows, and the schedule is certainly worth checking if near perfect acoustics appeal to you!
  • Enjoy the Observation Deck: The Observation deck–at Independence Wharf–provides iconic vistas of Boston for free! Contained with an old warehouse, there are both indoor and outdoor portions for your free viewing pleasure! Just be sure to bring some type of ID with you as it’s required.
  • Visit the MIT Museum: The Massachussetts Institute of Technology was established in 1971 and is now one of the most prestigious universitiies in the world. You can find a number of fascinating exhibits here pertaining to artificial inteligence and all other facets of technological research.
  • Tour the Samuel Adams Brewery: While it might be the smallest out of the Boston Beer Company’s many breweries, the Samuel Adams location is the only one that gives tours! The tours are either free or cheap and give you a chance to get to know the brand’s history and sample some beers while you’re at it.
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Osprey Daylite Plus

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10 Top Things to Do in Boston

Here are some of the best things to do in Boston that you really shouldn’t miss:

1. Walk the Freedom Trail

No Boston travel guide is complete without suggesting a walk on the terrific Freedom Trail. This pathway visits most of the city’s most important historical attractions including the Boston Commons, Bunker Hill Monument, and Paul Revere’s House. Best of all – it’s free!

2. Feast in the North End

Since this is the Italian Quarter, there really is nothing better to do than eat pizza and Italian food. You won’t have much trouble finding a place to eat considering every other shop is either a restaurant or bakery. You won’t find me complaining.

pizzas sitting on display in boston's italian north end
The North End AKA Boston’s Little Italy.

3. Catch the ferry to East Boston

One of the best places to visit in Boston (that may also be a bit surprising) is East Boston. This part of town, specifically around Lo Presti Park, offers unrivaled views of the city and the journey across Boston Harbor is pretty sweet too!

4. Visit the hallowed Fenway Park

Fenway Park is probably the most beloved structure in the entire city and is just about as important to Bostonians as anything. For the most Boston experience ever, catch a game here and sit in the legendary Green Monster.

Boston Red Sox forever!

aerial fenway park boston travel guide
Seeing the Boston Red Sox play at home is about as “Boston” as it gets.

5. Discover the Mapparium

What’s cooler for world travelers than walking inside a giant freakin’ globe?! Hidden inside the Mary Baker Eddy Library, this interactive art installation allows you to see the world from a whole different perspective. This is seriously a great spot for any interested in geography.

6. Snap some pics in Beacon Hill

Beacon Hill is probably the prettiest neighborhood in Boston thanks to its charming colonial architecture and cobblestone streets. While I loved visiting the historic State Building, nothing really tops the eminently quaint Acorn Street.

beacon hlll boston state building
The architecture in Boston is so satisfying.

7. Go for a run on the Esplanade

Boston is an active town and it seems like there’s always some type of organized workout going on. There is no better place to go for a run than the Charles River Esplanade. In the summer, this area is just gorgeous and will certainly give you something to think about while you sweat.

8. Have a picnic in the Boston Commons

One of the most classic and coolest places to eat in Boston is the Commons. This giant parkland is a gathering place for all kinds of folks. You’ll see plenty of people picnicking here in the afternoon.

boston commons park with historical statue in the summer
This is why the best time to travel to Boston is absolutely in the summer.

9. Get off the beaten path in Boston

There are tons of secret spots in Boston that only require a little extra effort to see. Mix things up by visiting the Ruins of Schoolmaster Hill, the Sacred Cod of State House, or the Ether Dome.

10. Visit the Boston Museum of Fine Arts

Containing over 450,000 works of art, the Boston Museum of Fine Arts is the 14th largest art museum in the world. Founded in 1870, the museum includes paintings, sculptures, and hosts fine temporary exhibitions alongside its permanent treasures. Admission is $27.

statue on display at museum of art while traveling in boston
No danger, he’s armless…
Small Pack Problems? 😉

My missus travels with all her clothes in ziplock bags: don’t be like my missus. UP YOUR PACKING GAME!

Packing cubes for the globetrotters and compression sacks for the real adventurers – these babies are a traveller’s best kept secret. They organise yo’ packing and minimise its volume too so you can pack MORE.

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Backpacker Accommodation in Boston

Boston has a huge variety of accommodation catering to all sorts of travelers. Whether you’re a backpacker, a working professional, or traveling on a family trip, there’s something for you in Boston.

I previously mentioned that lodging in Boston is very expensive. Unless you’re insistent on having a private apartment or room, I highly recommend staying at a hostel.

They’re affordable, fun, and of a high standard. There are many quality hostels in Boston, so don’t feel like you have to settle for a fuck-bucket of a party option.

Boston Fenway Inn bunkbed backpacking boston
Backpacker accommodation in Boston is a lot cleaner and cuter than some other US cities.

If you really wanted your own place, then you can check out Airbnb. Hotels are often bland and impersonal, not to mention expensive. There are some really cool Airbnb options in Boston that offer great experiences. I stayed in a great one on Newbury Street.

The best way to save on accommodation in Boston is to go camping. You’ll often have to stay quite far outside of the city, but if you have a car and some quality backpacking gear, then this problem can be alleviated. Just drive to the nearest subway stop and take the train into the city (driving in the city is a nightmare). Don’t forget a tent either!

The Best Places to Stay in Boston

Here are tons of places to stay in Boston–here are some of the best neighborhoods to choose from.

FIRST TIME IN BOSTON
Back Bay, Boston
FIRST TIME IN BOSTON

Back Bay

If you’re visiting Boston for the first time, there’s no better neighbourhood than Back Bay. Centrally located and well connected, Back Bay is close to everything.

ON A BUDGET
Downtown, Boston
ON A BUDGET

Downtown

Downtown is far and away the most iconic neighbourhoods in Boston. It is home to a number of historic sites and cultural gems, including Boston Common and Boston Public Gardens.

NIGHTLIFE
Chinatown, Boston
NIGHTLIFE

Chinatown

Chinatown is a small but vibrant neighbourhood located in central Boston. It is the fourth largest Chinatown in the United States and this neighbourhood is home to incredible restaurants and colourful shops.

COOLEST PLACE TO STAY
South End, Boston
COOLEST PLACE TO STAY

South End

Boston’s South End neighbourhood is one of the most overlooked and underrated areas of the city. Within South End, you’ll find some of the best restaurants and art galleries in the city and can enjoy a hip yet relaxed atmosphere.

FOR FAMILIES
Jamaica Plain, Boston
FOR FAMILIES

Jamaica Plain

For families with children, there’s no better neighbourhood than Jamaica Plain. A quiet and residential district south of the city centre, Jamaica Plain has charming restaurants, cute cafes and a great selection of green spaces to explore.

Boston Backpacking Costs

Boston is one of the most expensive cities in the USA, mostly because of astronomical property values.

Thankfully, this trend doesn’t affect tourism too much and Boston is still relatively affordable when compared to other major East Coast cities (New York and DC are much more expensive). Ultimately, Boston can be cheap, but only with the proper guidance and habits in place.

With plenty of tips to visit Boston on a shoestring budget, maybe you’ll even get by on $10/day.

A lower average daily budget for Boston will be around $60-$80. This includes a dorm bed, groceries, public transport, and some spending money.

boston skyline scene from behind a plant in summer
Traveling in Boston CAN be bougie, but it doesn’t have to be.

Without question, lodging will be your greatest expense in Boston. Yep, accommodation in Boston ain’t cheap. Unless you’re willing to splurge on a hotel or Airbnb – often just as expensive as those in New York – you’re gonna have to stick to the Boston hostels and guesthouses.

You can also look into urban campgrounds and utilize Couchsurfing if you like, but these options are limited.

The prices of food and drink vary widely. For example, the central districts of Boston and Cambridge can be particularly expensive.

Even Quincy Market, long hailed for its street food, is sorely lacking in truly affordable options these days. Hit up the outer suburbs of East Boston, South Boston, and Allston for cheaper offerings.

Public transport is cheap and effective in Boston, but since trips are one-way, tickets add up quickly. Consider buying a daily/weekly pass if you think you’ll be using transit often.

A Daily Budget in Boston

Here’s how much traveling in Boston costs, broken down by travel style:

Copy of Boston City Guide Daily Budget
ExpenseBroke BackpackerFrugal TravelerCreature of Comfort
Accommodation$0-$60$60-$180$180+
Food$10-$15$15-$30$30+
Transport$0-$10$10-$40$40+
Nightlife$0-$20$20-$30$30+
Activities$0-$15$15-$40$40+
Total per day:$10-$110$110-$220$220+

A Few Free Things to Do in Boston

If you’re looking to save some extra cash, then try doing one of these free things in Boston on your next visit!

Boston Duck Tour boat seen in water during a summer day
Admiring nature = free!
  • Freedom Trail – The lauded walkway that takes you through to many of most important historical attractions in Boston. Of course, the 2.5-mile walk itself is free but some locations may be ticketed. Highlights include Bunker Hill, Boston Commons, Paul Revere House, and Faneuil House.
  • Sam Adams Brewery – The treasured brewery offers free tours of their facilities and almost always gives out complimentary samples at the end. Yes, FREE BEER!
  • Boston Harbour – One of my fave things to do is to take a stroll down by Boston Harbor and feed the fresh sea breeze.
  • Museums – Many of Boston’s best museums offer free admission on certain days and/or at certain times. Check the websites of the following for more details: Bunker Hill, MIT Museum, ICA, Children’s Museum, Museum of Science, MFA, and Museum of Bad Art.
  • Open-air screenings – One of the most popular things to do in Boston in the summer is catch an outdoor movie. Many organizations arrange free film viewings at public spaces (parks, plazas, etc) in Boston. Most of these films are American classics too.
  • November Project – This is one of the best free things to do in Boston! Join this health-minded community for prearranged, free exercises in many of Boston’s public areas. Examples of activities include running, relays, and calisthenics.
  • Free festivals – There’s always a free event happening in Boston, especially during the summers.

Travel Tips – Boston on a Budget

It’s easy to spend without thinking, and even easier to go broke.

In hopes of helping you explore Beantown on the cheap, here are some Boston travel tips for folks on a budget. Follow these words of advice and you’ll find that your dollar goes much further!

night light trails boston travel guide
Boston just after sunset.
  • Always pre-fade before going out – Buying full-priced drinks at the bar is a great way to waste your money. Instead, buy booze at the store and drink with your friends at the hostel/their house/the park/anywhere besides the actual bar.
  • Cook at home as often as possible – Buying your own groceries and cooking at home will save you heaps of cash. This is where using Airbnb can come in handy.
  • Buy a special pass – If you’re planning on seeing a lot of the city, then you may want to invest a City Pass. This card will allow free entry into many of Boston’s must see attractions and even give you special rates for public transport.
  • Search for “1-Buck Shucks” – Dollar oyster deals are a New England staple! Search for the best oysters in Boston and pay next to nothing in the process. Be careful though; shit can feel weird after a couple dozen of these.

Why You Should Travel to Boston with a Water Bottle

We’re all aware of our plastic consumption infiltrating our precious oceans now… so do your part and keep the Big Blue beautiful!

You can’t save the world overnight, but you CAN be part of the solution! Small changes are easy, and they make a difference. So I hope you then become more inspired to continue being a responsible traveler.

Plus, now you won’t be buying overpriced bottles of water from the supermarkets either! Travel with a filtered water bottle instead and never waste a cent nor a turtle’s life again.

Save $$$ • Save the Planet • Save Your Stomach!
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Single-use plastic bottles are a MASSIVE threat to marine life. Be a part of the solution and travel with a filter water bottle.

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Best Time to Travel to Boston

I don’t think I’ve ever met a New Englander that really loved the weather there. Sure, some people may make lukewarm statements like “the weather is fine” or “I don’t mind it,” but to hear anyone say “I just adore the weather in Boston” is probably a sign of severe brain haemorrhaging.

boston fall foliage
Fall in Boston, you say?

The weather in Boston is notoriously uncooperative. Winters are frigid, windy, and prone to freak snowstorms. Summers are warm and sunny but unfortunately too short. Spring and autumn are like flakey friends – really enjoyable but, more often than naught, absent.

pink boston sunset in winter
Winter might be pretty, but as someone who lived in New England for 20 years, it’s the worst time to visit.

Summer is when Boston is full of out-of-towners. This sudden influx usually jacks up prices and creates congestion. Many Bostonians will also be fleeing to the coastal communities – e.g. The Cape – during this time, which can make the city feel a bit hallow.

The best times to visit Boston are probably during the summer’s shoulder seasons (April-May & September-October). The weather during these months is often reliable if not a little on the cool side. There will be fewer tourists in town, which means prices will be lower, and more students, which means the bars will be packed.

Mid-October is peak fall foliage in Boston and it’s an absolutely breathtaking period to visit New England. People from all over the East Coast flock to New England to see the trees turn a fiery color and this makes the city feel a little more alive for a couple more weeks.

Winters in Boston are lamentable. They are cruel, not because of their harshness but because of their deceptiveness. Winter temperatures usually hover around a reasonable 32-38 °F but Boston’s humidity makes the chill penetrate the bone. The wind also batters you and it’s not unheard of for a wind chill to cause the relative temperature to drop 20 degrees.

What to Pack for Boston

While your Boston wardrobe will be largely dependent upon the season and weather forecast, here are a few things you just shouldn’t head out without:

Product
Description
Traipse the CIty in Style!
Osprey Daylite Plus
Traipse the CIty in Style!

Osprey Daylite Plus

Any city slicker needs a SLICK daypack. In general, you can never go wrong with an Osprey pack, but with its array of awesome organisation, durable materials, and a comfy build, the Daylite Plus will make your urban jaunts buttery smooth.

Drink from ANYWHERE
Grayls Geopress Water Bottle
Drink from ANYWHERE

Grayl Geopress Filtered Bottle

Save $$$, save the planet, and save yourself the headache (or tummy ache). Instead of sticking to bottled plastic, buy a Grayl Geopress, drink water no matter the source, and be happy knowing the turtles and fishies thank you (and so do we!). 🙂

Pics or It Didn’t Happen 😉
Pics or It Didn’t Happen 😉

OCLU Action Camera

Wait, it’s cheaper than a GoPro and… better than a GoPro? The OCLU action cam is the cam for budget backpackers that want to immortalise all their wildest adventures – including that time you dropped it off a Himalayan mountain – WITHOUT breaking the bank.

Harness the Sun!
Solgaard Solarbank
Harness the Sun!

Solgaard Solarbank

Resourceful travellers know how to find power outlets anywhere on the road; smart travellers just pack a solar power bank instead. With 4-5 phone cycles per charge and the ability to top up literally anywhere the sun is shining, there’s no reason to ever get lost again!

Don’t Annoy Your Dormies
Don’t Annoy Your Dormies

Petzl Actik Core Headlamp

ALL travellers need a headtorch – no exceptions! Even in the hostel dorm, this beauty can save you in a real pinch. If you haven’t got in on the headtorch game, DO. I promise you: you’ll never look back. Or at least if you do, you’ll be able to see what you’re looking at.

Staying Safe in Boston

By most contemporary American safety standards, Boston is pretty tame. It used to be dangerous, but thanks to huge public safety initiatives, the city is now quite relaxed. Those planning a trip to Boston should not have to worry about personal safety IF they are aware of a few issues.

Like the rest of the world, petty crime is still a part of life in Boston. Pickpocketing has been known to occur in busy nightlife districts and on public transport. Carjackings and break-ins are not unheard of either. When visiting Boston, be sure to exhibit all of the usual travel safety precautions and to always have your wits about you, just to be on the careful side.

What happens when you say the Red Sox are shit?

The real way to get in trouble is if you started bad-mouthing the locals. Bostonians, though generally friendly, do not take kindly to being insulted and, after a couple of beers, will beat the shit out of anyone. This means talking shit about the Red Sox, saying something like Tom Brady is a pussy, or trying to impersonate their distinct accent (they really hate that last bit). Unless you’re really looking for a fight, just keep ye’ mouth shut.

If you’re caught in the crossfire in or outside of a bar, the police are never too far away. Many cops patrol the neighborhoods that are most prone to fights to break things up.

Sex, Drugs, and Rock ‘n’ Roll in Boston

While Boston is far from the biggest party city in the US, it is still home to some bars and nightclubs that will be sure to make for a good time. You can expect a wide variety of scenes that cater to all preferences: from Bijou in Chinatown to the famous bar scene in the North End, Boston absolutely has some places to get lit. The only downside: almost all nightlife in Boston shuts down around 2 AM.

guy djing at a dark club with red heart beat graphic behind him
Waves and vibes… until 2 AM.

While this would sound early if you were traveling in New York City, it’s actually when places have to legally shut down in Boston. I told you Boston feels more quaint and old-timey than other East Coast cities!

As for other things, you can definitely find every party favor under the sun while backpacking Boston. Luckily, recreational weed is legal and you can grab it from any dispensary.

For anything else, you’re going to have to know someone. But be careful: party drugs are being laced with fentanyl all over the US these days. Always use a testing kit and do some research prior to partaking in drugs on the road!

Getting Insured BEFORE Visiting Boston

Let’s get real: traveling without insurance in the USA is risky. Especially with the infamous (and ridiculous) for-profit health system. So do consider getting good travel insurance sorted before you head off on an adventure to Boston.

I have used World Nomads for years now and made a few claims over the years. They’re easy to use, professional, and relatively affordable. They may also let you buy or extend a policy once you’ve started your trip and are already abroad which is super handy.

A banner creative for World Nomads travel insurance

It’s good to get lost sometimes, but it’s also good not to get too lost. There are people that want you home in one piece.

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Click the button below to get a quote on your insurance or read our in-depth review of World Nomads’ coverage. And then… let the shenanigans begin. 😉

How to Get Into and Around Boston

There are many ways in and out of Boston as the city is well-connected by land, air, and nautical routes. Those planning a trip to Boston should have little problem arriving into and departing from the city.

Boston’s main airport is Logan International and is serviced by many flights, both domestically and internationally. As the primary gateway for all of New England, Logan receives a lot of passengers on a daily basis.

Boston Logan is connected to the city via a subway line (Blue) and bus line (Silver). The airport is located close to the city itself so those who prefer taxis shouldn’t have to pay an arm and a leg.

drone photo boston travel guide
A bird’s eye view of Boston.

There are several long-distance trains that stop in Boston. Amtrak, the largest train network in the USA, connects Boston with cities as distant as Chicago, Washington DC, and Portland (Maine).

Note that Boston has two train stations – North Station and South Station – and each manages different routes. Trains to/from northern destinations terminate at North Station while southern destinations terminate at South Station.

Being a part of the Eastern Seaboard, Boston’s roadway system is very well-developed. Those who are on a New England road trip or an East Coast road trip will have no problem getting to Boston by car. Be aware that New England has lots of toll roads.

Traveling by bus can be a preferable way of getting in and out of Boston. You’ll avoid paying tolls and gas as well as avoid the stress of driving in the city. (East Coast drivers are aggressive.)

There are frequent buses linking Boston to all major Northeastern cities like New York, Philadelphia, Portland (Maine), and Providence. There’s even a direct bus from Boston to Montreal, Canada.

Getting Around Boston

Contrary to what Boston’s skyscrapers might indicate, Boston is actually a compact city. This means that most will be able to manage the city with only public transport, rideshares, and two feet.

Boston benefits from a very effective public transportation system. Subway lines, locally referred to as “The T,” connect nearly every major district in the Greater Boston area. If a neighborhood isn’t conveniently located near a subway line, there are plenty more buses. There are even water taxis that will take you across the Boston Bay to East Boston and Charlestown.

Boston Guided Trolley Tour
Be sure to try out the trolleys when you’re in Boston.

One-way tickets on the T cost $2.50 and include a bus transfer, while one-way tickets for exclusively the bus cost $2. An unlimited one-day ticket costs $12.50 and is likely your best option.

If you think that you’ll be using a lot of public transport, consider picking up a LinkPass, which offers unlimited rides for a certain amount of days. LinkPasses come in 1 and 7-day increments.

Honestly, you can probably see most of Boston’s points of interest on foot. Most of the top attractions in Boston are located in the Downtown area and anything else just requires a quick ride on the T.

Boston is a very pedestrian-friendly city and is actually better enjoyed from street level, anyway. Granted, you’ll probably want to use the buses and trains during the winter months.

Biking is a popular way of getting around Boston as it’s a flat city, but poor weather and bike infrastructure make biking inconvenient at times.

Buying a Transit Pass in Boston

It is highly recommended that you pick up a CharlieCard while touring Boston as they are convenient and offer discounted rates ($2 for the subway, and $1.50 for buses). CharlieCards are free themselves and can be recharged at major ticketing machines.

bus iconUse Bookaway to find the best deals on transport – buses, planes, trains, and ferries. It’ll save you a load of time when organising transport and you’ll probably nab an EPIC DISCOUNT too!

Book your transport on Bookaway NOW. Get the best price for the best ride… then use those savings to buy the best feed in town!

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Working and Volunteering in Boston

Like most cities in the US, Boston isn’t exactly a digital nomad hotspot. Everything is quite pricey and, simply put, the digital nomad scene just isn’t there.

This doesn’t mean you can’t work online from Boston! You absolutely can: a city associated with so many universities certainly isn’t lacking in Wi-Fi-having coffee shops.

As for finding a job in Boston, the US has very strict work laws, so you won’t be able to do that without US citizenship or another permit. Volunteering is possible, though still very uncommon compared to the scenes in Europe or Australia.

If you want to find a reputable place to volunteer, we at The Broke Backpacker use Worldpackers, a neat online community that connects travelers with volunteering opportunities all over the globe. The platform is review-based and honest so you’ll know what you’re getting into BEFORE you arrive!

Worldpackers: connecting travellers with meaningful travel experiences.

Nightlife in Boston

boats in water and fireworks in sky boston travel guide
The 4th of July is always a fun time in Boston.

Boston really bats above its weight class when it comes to nightlife with a huge selection of bars catering to all types of people.

Boston has a couple of key crowds when it comes to the bars. They are 1. Tourists, 2. Students, and 3. Locals. Each has an area that they like to hang out in.

The tourists mostly end up going out around Downtown as this area has the most things to do at night in Boston. The Theater District/Chinatown hosts the majority of the city’s nightclubs and is particularly rowdy.

Nearby Faneuil Hall gets plenty of action too. Boylon, Canal, and Newbury Street are also active, though you’d be hard-pressed not to find a busy street in Downtown Boston on the weekend.

Students tend to hang out around the college campuses and student housing neighborhoods. Allston, a well-known student suburb, has lots of cheap drinks for those poor students.

On the other hand, Cambridge Central Square attracts mostly Harvard kids and is a bit more expensive (thanks to daddy’s allowance).

Local Bostonians tend to go out wherever they feel like, be it Downtown or Dorchester. Fenway is ground-zero for local sports fans and goes absolutely nuts on game days.

The hip South End is getting increasingly rambunctious. If you’re looking for a classic Irish pub, complete with gruff working-class folk, there’s no better place than South Boston.

Note that Boston is subject to Blue Laws, which, essentially, limit when, where, and how much you can drink. These Blue Laws are very strict, much to the ire of the locals, and drinking in Boston can be a hassle sometimes. Thanks to Blue Laws, bars close at 2 am promptly on the weekends in Boston and happy hour is banned city-wide.

Dining in Boston

Boston is a world-class culinary destination with an immense selection of restaurants and bars to choose from. Here, you’ll be able to find everything from local delicacies – like lobster rolls and cream pies – to ethnic delights from all corners of the globe. Boston baked beans are the obvious choice too.

Top it off with a heavenly pint of New England lager, and you have all the makings of a foodie paradise. And if you want to ensure you don’t miss anything–there are plenty of quality Boston food tours to choose from!

clam chowder in a breadbowl boston travel guide
Did you really visit Boston if you didn’t try the New England clam chowder?

Boston’s food scene is mostly defined by New England cuisine which is, essentially, a blend of the many cooking styles brought over by the original immigrants. New England foods are often hearty and rich, which is great for battling those cold winter days.

Baking is the primary means of cooking so you shouldn’t have to worry too much about greasy food (unless you purposely seek them out). Deserts and sweets are particularly well-loved in New England.

The best Boston food.

Of course, being on the coast and all, seafood is the foremost staple of the Boston diet. And, by God, is it awesome. Lobster rolls, chowders, and oyster shooters are just some of the dishes prepared to near-perfection, much to the pride of the locals. Really, nothing beats a clambake on a Boston summer day.

Boston still has a large immigrant population and there are a huge amount of international restaurants strewn throughout the city. Being the Italian quarter, the North End is where you’ll find the best pasta among other Italian staples. East Boston is one of the best places to eat in the city as it hosts a huge selection of ethnic restaurants from Portuguese to South American to Asian.

You’ll find Irish fare just about everywhere in the city but the most “authentic” will be found in South Boston.

Slick Restaurants and Cheap Eats

Eating in Boston can break the bank quickly. Luckily, there are still many backpacker-friendly eateries to be found:

  • Kelly’s Roast Beef: Aside from their iconic roast beef sandwiches that come in just under $10, you can also taste some delicious lobster rolls, New England clam chowder, and even fried scallops without breaking the bank.
  • Anna’s Taqueria: A neighborhood staple since 1995, you can find many of Anna’s delicious Mexican menu items for less than $10.
  • Sullivan’s: Love hotdogs? Even if you don’t–you can’t pass up this famous Sullivan’s staple which also specializes in Boston seafood favorites.
  • Bánh Mì Ba Le: For the freshest Vietnamese in the city at amazing prices, grab a banh mi sandwich from this famous no-frills shop in Dorchester.
  • Ernesto’s Pizza: For 30 years, hungry Bostonians have flocked to Ernesto’s–located in the famous North End–for its gigantic pizza slices fit for all budgets!
  • Ho Yuen Bakery: For authentic and delicious Chinese food at Southeast Asia prices, look no further than Ho Yuen Bakery, where you can’t leave without trying one of their buns.

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    Day Trips from Boston

    Want to get out of the city? Visit one of these places near Boston for a chance to stretch your legs and experience some of New England’s best scenery.

    cape cod sunrise
    Nothing beats a Cape Cod sunrise.
    • Cape Cod – The iconic Cape is Boston’s idea of a vacation. Famous for its endless beaches, charming towns, and historic lighthouses, Cape Cod has become the poster child for the New England coast. Lots of people travel to the Cape in the summer and spend an extended period of time here, either for work or play.
    • Salem – This historical town was made famous by its gruesome Witch Trials. Anyone who has had any interest in New England history, or the occult for that matter, ends up visiting this town. Contrary to its grim reputation, Salem is actually a fairly affluent place these days.
    • Walden Pond/Concord – Boston and the surrounding countryside were the stomping grounds for one of the greatest American intellectuals: Henry David Thoreau. Walden Pond, the setting for Thoreau’s revolutionary Walden novel, is located not too far away from the city itself. Visiting Walden in addition to the nearby historical Concord makes for an excellent day trip from Boston.
    • Portland, Maine – The charmingly unassuming Portland, Maine is a mere 2-hour drive away from Boston and makes for a great road trip. Spend the day exploring the rugged coastline between Massachusetts and Maine, hitting up as many beaches as you can. Arrive in Portland and then grab a fresh lobster at the Old Port with a nice hearty beer.
    • Rhode Island – Providence and the rest of Rhode Island are like New England condensed in one state. Here, you’ll find all of the staples of the region including coastal villages, brilliant fall foliage, and tons of history. This is one of the best places to visit near Boston.

    Getting Off the Beaten Path in Boston

    Luckily–it’s easy to get off the beaten path in Boston! Most tourists just head to the same few places, so if you’re looking for something different, look no further. From the lush Arnold Arboretum at Harvard to the interesting Castle Island, Boston has a lot to offer that you might miss without a lot of time or quality research.

    Due to its pedestrian-friendly nature, Boston is a place you can simply set out to explore and see where you end up! This is my favorite way to get acquainted with a new city, and can surely lead to some unexpected encounters.

    Boston also has plenty of cool day and weekend trip options to consider. Cape Cod is definitely worth the drive, especially if you happen to be in the area on a weekday when it tends to be less crowded.

    FAQs About Traveling in Boston

    You’ve got some questions before traveling to Boston, and I’ve got answers! Here are some FAQs to know before you go.

    Final Advice Before Visiting Boston

    Boston is an incredibly unique city. From the distinct Boston accent to its plethora of lobster rolls, Boston has the rare ability to make you feel like you’re in a town while strolling about a state capital. Those who have gotten acquainted with it know the small city is easily one of the coolest places in the US–hands down.

    And now that you’re done with the best Boston travel guide, I hope you yourself are hella’ excited for your upcoming adventure in Beantown!

    Be sure to hit up those Boston hotspots, and if you can swing it, there’s no better way to experience Boston culture than by watching a game at Fenway Stadium.

    But do take the time to get off the beaten path a bit too and see Boston beyond its famous locales. Aim to get lost, or take one of the many epic day trips. Regardless of what you plan to do on your vaction in Boston, you’re absolutely in for a grand time.

    Now, what are you waiting for? Book that hotel and ready for your Boston trip!

    boston river and skyline on a sunny summe day
    Nothing quite like a summer day in Boston!

    Thanks for reading – that was fun! 😀

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