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 like Matt Damon or Ben Affleck from Good Will Hunting anymore. (Best not to dwell too much on the latter part, as locals never really appreciated out-of-towners trying to talk like this anyway.)

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 just a really gorgeous city, Boston is jam-packed historical sites, great food, and unabashed character. For visitors and residents alike, there is so much to do and see here that having a good Boston travel guide would be pay off dividends.

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

We’ve included information like cheap things to do in Boston, where to stay on a budget, sample Boston itineraries, and the best places to drink.

With this guide in hand, you’ll be ready to hit the streets of Boston and to explore them as the locals do. So what are we waitin’ for?! Let’s get to it people!

10 Things to Do and See in Boston

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, and the Paul Revere House. Best of all – it’s free!

2. Spend a rainy afternoon at the Boston Public Library

If you are looking for cheap things to do in Boston, might I suggest going to the library? For some people that may sound lame, but the Boston Public Library is actually quite cool.

The architecture and ambiance is astounding and one could easily spend the entire afternoon just wandering through its hallways. Try picking a book from our Boston reading list and hunkering down for a bit of reading. 

public library boston travel guide

3. Catch the ferry to East Boston

One of the best Boston vacation ideas (that may also be a bit surprising) is a visit to 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.

aerial fenway park boston travel guide

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. Photo ops in Beacon Hill

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

beacon hlll boston state building

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 picnicing here in the afternoon.

boston commons park

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. Boston Museum of Fine Arts

Containing over 450,000 world of Art, the Boston Museum of Fine Arts is the 14th largest art museum in the world. Founded in 1870. the museum includes painting, sculpture and hosts fine temporary exhibitions alongside its permanent treasures. Entry for non-members is $250.

11. Feast at 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 us complaining.

north end boston travel guide

Best 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!

  • 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, among others.
  • Free festivals – There’s always a free concert or performance going on in Boston during the summer. Check this website for a list of free events in Boston.

Boston Travel 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 our help, you can travel to Boston on the cheap and avoid the worst of Boston’s expenses. We’re going to provide you with plenty of tips to visit Boston on a shoestring budget. Who knows; maybe you’ll even get by on $10/day.

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

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 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 very expensive for dining and drinking. Even Quincy Market, long hailed for its street food, is sorely lacking in 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.

Below is a breakdown of a daily budget in Boston including average costs of each expense.

park in boston travel guide

Guide to Boston Travel Costs

Copy of Boston City Guide Daily Budget
 AccommodationFoodTransportActivitiesAverage Daily Cost
Broke Backpacker$35$15$8$20$78
Frugal Traveler$70$25$20$35$150
Creature of Comfort$300$90$35$50$475

Boston Budget Travel Tips

night light trails boston travel guide

It’s easy to spend without thinking, and even easier to go broke. If you want to visit Boston on the cheap, then you’ll have to be strict with your spending habits.

For your benefit, we’ve created a list of tips for visiting Boston on a budget. Follow these words of advice and you’ll find that your dollar goes much further.

  • 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.
  • 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.
  • Use a water bottle – Save money by investing in a good water bottle and then drink from the tap. Boston’s water is delicious and totally fine to drink.
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Luggage Storage in Boston

If you’re exploring Boston before check-in or after checkout, leave your bags with LuggageHero, a network of more than 30 storage points in local shops located around traffic hubs and popular districts. Maybe you want to walk the Freedom Trail, stroll through Boston Common, or watch a game at Fenway Park. Just use the map at the LuggageHero reservation platform to find a handy verified storage site. Each bag receives a safety seal, and the bag and contents are insured for $3,000. If your plans change, there’s no cancellation fee.

Where to Stay in Boston (on a Budget)


HI Boston

Hostelling International Boston provides towels, soap, coffee, and baked goods, making it one of Boston’s coolest hostels!

  • $$
  • Free Breakfast
  • Washing Machine

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.

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

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

If you really wanted your own place, then we suggest you stick to 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, 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!

Refer below to read about some of the best hostels in Boston and read our comprehensive travel guide to Boston’s hostels here.

boston travel guide chinatown neighborhood

Overall Best Hostel in Boston – HI Boston

A very stylish and sociable hostel conveniently located in Chinatown. Has everything that a superlative hostel should including a wide range of facilities, helpful staff, and clean rooms. There’s a large free breakfast every morning and an enormous kitchen for preparing every other meal.

HI Boston

Best Party Hostel in Boston – Backpackers Hostel & Pub

Can’t be bothered to leave the hostel to grab a beer? Well, this hostel has a pub on-site, which means you don’t need to deal with those strange Bostonian liquor stores.

The hostel is located a bit out of the way but, luckily, there is a shuttle that will ferry you to the nearest subway stop. No promises on whether or not they’ll drive your drunk ass though.

Backpackers Hostel & Pub best hostels in Boston

Best Hostel for Solo Travelers in Boston – Abercrombie’s Farrington Inn

A quieter, eminently charming hostel suitable for introverted types. It is located a bit outside of the busy downtown area in the Allston neighborhood, which is mostly inhabited by families and students. Those are looking to socialize though will find plenty of bars nearby.

Abercrombie's Farrington Inn best hostels in Boston

Best Airbnb in Boston – Studio in Prime Location

Spack dab in the heart of Back bay is this astonishing home that offers one of the most comfortable stays in Boston. On the lively street of Newberry, you have access to the most premier shopping in the city and the award-winning restaurants you’ve only seen on tv. Speaking of food, the kitchen is small but does have everything you need to cook a quick meal, but being in the popping neighborhood, you will most likely be enjoying all the cafes he neighborhood has to offer anyways.

Boston Accommodation Travel Guide

Sometimes you need a roof over your head; we know the feeling. Other times, you’re doing everything you can save a nickel and dime.

If you’re trying to the cut the costs of travel to Boston, then maybe it’s time to stay somewhere besides a hostel or apartment. If you need to save money, try one of these:

Couchsurf! – Couchsurfing is the best way to save on cash when it comes to accommodation since most of the time you’re crashing for free. Staying with a local host is also a great chance to experience a more authentic side of the city and to visit hidden Boston.

Problem is couchsurfing is really popular (duh, it’s free) and demand often outstrips supply. Hosts are picky as well so you’ll need to impress them with an eye-catching message. Definitely try couchsurfing but be ready to be rejected.

Tap into your backpacker network – You never know when you have a friend in a foreign city! If you’ve traveled a lot, you may have met someone from Boston or know someone who knows someone.

Reach out to people! Ask to stay with people for a night or two in exchange for cooking dinner or a bottle of wine. If you don’t know anyone in the city, ask your friends if they do – travelers understand the struggle and are usually more helpful than you think.

Camping – Urban camping is a growing trend in many cities. These campsites are comfortable, sociable, safe, and cheap. They are often located on the outskirts of town, which means they are quieter too.

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 – 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, end 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.
cape cod sunrise

How To Get Around Boston

Getting in and out of 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.

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.

drone photo boston travel guide

How to get around Boston

Contrary to what Boston’s large population numbers 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,” connects nearly every major district in the Greater Boston. 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.

One-way tickets on the T cost $2.50 and include a bus transfer, while one-way-tickets for exclusively the bus cost $2. It is highly recommended that you pick you 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.

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.

How To Stay Safe Boston

By most contemporary American crime standards, Boston is pretty tame. Boston used to be dangerous, but thanks to huge public safety initiatives has definitely calmed down. Those planning a trip to Boston should not have to worry about personal safety IF they are aware of a few issues.

st patricks day boston resident

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.

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 Redsocks, 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.

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Travel Insurance for Boston

Traveling without insurance would be risky so do consider getting good backpacker insurance sorted before you head off on an adventure.

I have been using World Nomads for some time 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.

If there’s one insurance company I trust, it’s World Nomads. To find out why I use World Nomads, check out my World Nomads Insurance review.

Getting an estimate from World Nomads is simple – just click the button or image below, fill out the necessary info, and you’re on your way!

 3-Day Itinerary for Boston

The following is a sample 3-day itinerary for touring Boston. Most of the top destinations that were already mentioned in this Boston travel guide are covered in this section.

map of boston travel guide
Locations are: 1. Fenway 2. Back Bay 3. Copley Square 4. Boston Commons 5. Beacon Hill 6. Northend 7. Long Wharf 8. Chinatown/Leather District 9. South End 10. Dorchester 11. South Boston 12. South Boston Waterfront 13. Logan International 14. East Boston 15. Charlestown 16. MIT 17. Central Square 18. Harvard 19. Allston 20. Green Necklace. Map of Boston not to scale. 

Day 1: Downtown Boston

On the first day of our Boston travel guide, we’re going to spend the entire day walking from Fenway to Northend. Along the way, we’re going to hit up all of the most eminent points of interest in Boston including, but not limited to, the Boston Commons and Quincy Market.

Make sure you have a comfortable pair of shoes because it’s going to be a long day!

Start by catching the T all the 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 if 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 head for 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.

downtown boston travel guide

Day 2: Visiting Cambridge

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 important colleges in the world – Harvard and MIT.

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

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 and most 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). MIT is very different from Harvard, in both essence and appearance.

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.

mit great dome cambridge boston travel guide

Day 3: South and East Boston

On the final day of our travel guide for Boston, we’re going to explore the edges of the city. We’ll drop by the infamously unabashed South Boston, revisit the outskirts of Downtown, and then finish at the tragically underappreciated East Boston.

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

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 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 South Boston 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 Tea Party Museum.

Wrapping 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.

The Long Wharf is home to many of the city’s most well-known attractions, including the Boston Aquarium and Quincy Market.

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.

harbor and boat boston travel guide

Best Time of Year to Visit Boston

I don’t think I have 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 hemorrhaging.

The weather in Boston is notoriously uncooperative. Winters are frigid, windy, and prone to freak snowstorms. Summers are warm but sometimes uncomfortable due to high humidity. Spring and autumn are like flakey friends – really enjoyable but, more often than naught, absent.

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 degrees 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.

boston fall foliage

Eating and Drinking 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.

Top it off with a heavenly pint of New England lager, and you have all the makings of a foodie paradise.

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.

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, 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 fair just about everywhere in the city but the most “authentic” will be found in South Boston.

boston bakery deserts

Nightlife 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.

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.

Books to Read on Boston

Check out this Boston reading list to learn more about the city! Each novel takes place in and around Boston and does a good job of exploring the city.

The Backpacker Bible – Get it for free! Learn how to ditch your desk and travel the world on just $10 a day whilst building a life of long-term travel with an online income. To inspire and help the next generation of Broke Backpackers, you can now grab ‘How to Travel the World on $10 a Day’ for free! Get your copy here. 

Walden – This transcendental masterpiece by Henry David Thoreau helped modern Americans rediscover nature and her beauty. Written outside of Boston at Walden Pond.

Mystic River – A murder shakes a traditional Bostonian family and causes the whole neighborhood to be turned upside down. It inspired the award-winning film of the same name.

Infinite Jest – One of the most important novels of the 21st century explores the current nature of the American Dream through the antics of a screwed-up family. Equally funny as it is revelatory.

The Bostonians – A highly influential novel that follows the trials and tribulations of a Bostonian feminist. Critically panned at the time but still managed to become a central figure in the Women’s Rights Movement.

Being a Responsible Traveler in Boston

Reduce your plastic footprint: Perhaps the best thing you can do for our planet is to make sure you do NOT add to the plastic problem all over the world. Don’t buy one-use water bottles, the plastic ends up in landfill or in the ocean. Instead, pack a tough travel water bottle.

Go and watch A Plastic Ocean on Netflix – it’ll change how you view the plastic problem in the world; you need to understand what we are up against. If you think it doesn’t matter, get off my fucking site.

Don’t pick up single use plastic bags, you’re a backpacker – take your daypack if you need to go to the shop or run errands.

Bear in mind, that many animal products in countries you travel through will not be ethically farmed and won’t be of the highest quality. I’m a carnivore but when I’m on the road, I only eat chicken. Mass-farming of cows etc leads to the rainforest being cut down – which is obviously a huge problem.

Need more guidance? – Check out our post on how to be a responsible backpacker.

Visiting Boston will bring you ample opportunities to participate in debauchery, and it is very important to have fun, let loose, and get a bit wild at times. Most trips I have been on across the world have included at least a few mornings where I wake up knowing I went too far.

But there are some things that will put you in the category of a straight up jackass if you do them. Being super loud and obnoxious in a tiny hostel at 3 AM is a classic rookie mistake. Show your fellow travelers respect whilst traveling in Boston and anywhere else for that matter!

jf kennedy library boston travel guide

Want to learn how to travel the world on $10 a day? Check out the Broke Backpacker’s Bible for FREE!

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