Located in the US state of Massachusetts, Boston is one of New England’s most picturesque waterfront cities. This modern metropolis still retains its old-worlde charm, and the whole city tells tales of its history and significance in American culture.

Boston is loaded with sights and attractions that’ll make you feel like you’ve stepped into a time machine! However, you don’t have to be a history-lover to enjoy this city. Boston has a vibrant nightlife scene, out-of-this-world cuisine and plenty of outdoor activities that will make your trip to this charming New England city as memorable as possible!

Boston is the perfect place to take your next vacation. It has a compact city center, loads of tourist attractions, and easy to use public transportation that’ll make your trip leisurely yet eventful!

If you’re looking for things to do in Boston this weekend, check out this helpful guide that’ll ensure you make the most of your weekend getaway!

Insider Tips for an AMAZING Weekend in Boston

2 days in Boston will give you plenty of time to explore this historic city, but the key to spending your weekend wisely is staying in central Boston! This will mean you save travel time and costs moving between the various things to do.

Know Where to Stay in Boston

Boston has many accommodation options to choose from, with prices to suit all budgets!  

Whether you’re looking for a friendly Boston hostel, a budget hotel, or a lavish 5-star room, you’ll want to make sure the location is near to the main attractions, so your Boston itinerary is as accessible as possible!

Our Favorite Hostel – HI Boston

HI Boston, Boston
HI Boston is our favorite hostel in Boston!
  • Male, female and co-ed dorm rooms available
  • Clean, comfortable and modern
  • Free breakfast and WIFI

HI Boston is centrally located next to most of the city’s top attractions, including Boston Common and Chinatown. There is also a subway stop within walking distance. This hostel has a large community kitchen and lounge area where guests can socialize.

Our Favorite Airbnb – Studio in Prime Location

Studio in Prime Location
Studio in Prime Location is our favorite Airbnb in Boston!
  • Spack dab in the heart of Back bay is this astonishing home that offers one of the most comfortable stays in the city. It’s definitely one of the best Airbnbs in Boston.
  • Located 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.

Our Favorite Budget Hotel – Boston Hotel Buckminster

Boston Hotel Buckminster, Boston
Boston Hotel Buckminster is our favorite budget hotel in Boston!
  • Close to Fenway Park and public transportation
  • On-site dining and fitness center
  • Microwave and refrigerator in every room

The Boston Hotel Buckminster is located in a great area of Boston. You’ll be within walking distance to many of the city’s top attractions as well as restaurants, bars, and shops. This historic building is well maintained and includes all modern amenities.

Our Favorite Splurge Hotel – Boston Park Plaza

Boston Park Plaza, Boston
Boston Park Plaza is our favorite splurge hotel in Boston!
  • Restaurant on-site and room service available
  • Two fitness facilities offering personal training and group fitness classes
  • Every room has a coffee machine

Located in the heart of Boston, this lavish hotel has it all! The rooms are large and spacious and equipped with a flat-screen TV, black out shades, a refrigerator, and more! All rooms also include city views!

Know How to Get Around in Boston

Getting around in Boston is easy and convenient. There are a few different options for transportation around the city, the main forms being the subway, bus, and on foot.

Driving can be a bit of a challenge if you’re unfamiliar with the city. If you decide to drive then be prepared to navigate old and outdated roadways and pay a stiff price for parking.

Taxi’s and ride-sharing apps such as Uber and Lyft are great options for quick and reliable transportation. Your driver will be more familiar with the layout of the city and you won’t have to pay parking fees!

The Massachusetts Bay Transportation Authority, or MBTA is Boston’s public transportation system. The subway is the most popular form of public transportation and is identifiable by a large “T.” The bus, commuter rail, and ferry are other options for transportation around Boston.

To ride the MBTA you must purchase a paper ticket called a “Charlie Ticket,” or a plastic card, called a “Charlie Card.” These can be purchased at electronic fare vending machines, at various local stores and select T stations.

Boston is a compact city and all of the main tourist attractions are within pedestrian friendly walking zones. All you need is a map and a good pair of walking shoes! For more info, visit our awesome Boston Travel Guide.

Travelling to Boston? Then plan yo’ trip the smart way!

With a Boston City Pass, you can experience the best of Boston at the CHEAPEST prices. Discounts, attractions, tickets, and even public transport are all standards in any good city pass – be sure invest now and save them $$$ when you arrive!

Buy Your Pass NOW!

Boston Nightlife Guide

Boston Nightlife Guide
Boston has some amazing nightlife options!

Weekends in Boston are the ideal time to experience the nightlife. Different areas of the city have different options for going out.

Here are the best districts in Boston to experience the vibrant nightlife!

Theatre District

  • From late-night clubs, to casual wine bars, there’s something for everyone!
  • Prices to suit all budgets – inexpensive to high-end
  • Easily accessible by public transportation

You can’t go wrong going out in the Theatre District! This area of the city has nightlife options for everyone. The Tam is one of the best dive bars in the city, it has a laid-back vibe, casual atmosphere and affordable prices. Or, check out Stoddard’s Fine Food & Ale for vintage cocktails and craft beer in a historic setting.

Central Square

  • Known for its wide variety of ethnic restaurants, live music venues, and bars
  • Up-and-coming area of Boston
  • Different options to suit everyone’s preference

Central Square is a neighborhood in East Boston. It has an eclectic range of nightlife options. Check out the Middle East Restaurant and Nightclub for an eventful evening. This club combines Middle Eastern cuisine with Boston’s rock and roll music scene. You’ll find at least one performance every night of the week!>

Fenway Park

  • Sports bars, dance clubs, live music venues, eateries, and more
  • One of the most lively areas to enjoy your Boston weekends
  • Concentration of nightlife options are centered around Lansdowne Street

Fenway Park is an area of the city where Boston’s sports culture and nightlife thrives. It doesn’t have to be game-day to draw a crowd, this area stays busy year-round. Check out Lucky Strike for 3-stories of fun; this venue features a bowling alley, dance floors, lounge area, and more!

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!

Boston Food Guide

Boston food
Boston has a delicious food scene!
Photo: Pat David (Flickr)

Food is an integral part of any holiday getaway! If you’re exploring Boston in 2 days, here are a few options to check out to experience the local food culture!

Best Dining Experience – The Union Oyster House

  • The best restaurant in the city for seafood lovers
  • Built in 1771 and turned into a restaurant in 1826
  • Enjoy Boston specialities like New England clam chowder and Boston baked beans

The Union Oyster House is one of the oldest restaurants in the United States, and registered as a National Historic Landmark. This historic eatery serves classic New England seafood specialities. It has hosted famous patrons across the decades, including Presidents, actors and authors. Mix history with dining for the ultimate Boston culinary experience!

For a Social Dining Experience – The Q

  • Simmering pot of soup stock with a variety of raw east Asian ingredients you prepare at the table yourself!
  • Chinese cooking method that allows for family-style dining
  • Great for a casual and social dining experience

In a manner similar to fondue, you grab and dip your food into a hotpot of freshly made broth. The pot is kept simmering in the middle of the table while everyone cooks their favorite raw ingredients, just the way they like them! Choose your favorite broth flavor and your favorite ingredients, including veggies, seafood, and meat.

The Best Market – Boston Public Market

  • A great way to sample the local culinary flavors of Boston
  • Indoor, year-round market, open everyday
  • Casual style eating, great for groups and people with different dietary needs

Boston Public Market has a large and diverse variety of local food and drink options. From snacks, to mains, to dessert, to drinks, there’s something for everyone! The atmosphere is hip and trendy and all of the food and products are made locally. To check out what the locals eat, make sure to include this in your Boston weekend trip!

If you have time, you could even take one of the many fantastic food tours in Boston!

Sporting Events in Boston

Boston sports
Boston has some really cool experiences for sports lovers!

A Boston weekend trip is the perfect time to experience the city’s sports culture. Here are a few of our favorite activities to enjoy on your weekend away.

Watch the Red Sox at Fenway Park

  • One of America’s most beloved ballparks
  • Watch a match and immerse yourself in the electric feel of game-day
  • The oldest ballpark in Major League Baseball

Bostonians are loyal Red Sox fans, and a trip to Fenway Park is a must see attraction for sports enthusiasts! If your Boston weekend coincides with a home-match, watch a game and experience the local sports culture. Game-day is sure to bring high energy and a lively atmosphere! Can’t catch a game? Tours of the stadium are also available year-round

Stretch Your Legs at Millennium Park

  • A great place to get some exercise and fun for all ages
  • Enjoy scenic views of the Blue Hills, Newton’s hills, and downtown Boston
  • Picnic tables, playground, toilet facilities and lots of parking

Millennium Park is an outdoor oasis located on the outskirts of Boston. Enjoy 6-miles of accessible trails, large grassy fields, a canoe launch and gorgeous views. There’s enough space for everyone to partake in whatever outdoor activity they enjoy. Go for a run, walk your dog, fly a kite, or kick around a soccer ball.

Canoe or Kayak the Charles River

  • A different way to experience the city and get a bit of exercise
  • A great activity for outdoor enthusiasts spending two days in Boston
  • Fun for all ages and skill levels and perfect for the whole family

Enjoy breathtaking views of Boston’s skyline while experiencing the tranquility of floating on water. Escape the hustle and bustle of the city and head out on the water for a relaxing reprieve. Have a leisurely paddle by yourself, or book a tour and journey along with others as you enjoy a panoramic sea view of the city!

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.

Or, y’know… you can stick to ziplock bags.

View Our Fave Cubes Or Check Out the Sacks!

Weekend Cultural Entertainment in Boston – Music/Concerts/Theatre

Boston entertainment
There are plenty of shows and events in Boston!
Photo: Bill Damon (Flickr)

>A weekend trip to Boston will give you plenty of time to explore the city’s music and theatre culture. Add a stop at one of these venues to your Boston in 2 days itinerary for an entertaining experience.

Boston Opera House

  • Hosts popular broadway shows, musicals, ballet performances, and concerts
  • Wonderful selection of performances, amazing acoustics and good visibility
  • Open and operating since October of 1928

The Boston Opera House is the best place to go in the city to experience the city’s performing arts culture. This grand theatre is designed in a combination of French and Italian styles. It is wonderfully decorated with ornate detail and is a piece of art in its own right.

House of Blues Boston

  • Friendly vibe and casual aesthetic
  • Diverse selection of live music, from bluegrass to techno
  • Rock- and blues-themed chain

Enjoy dinner and a show at the House of Blues in Boston. This Boston attraction makes for an entertaining night out. The venue is the perfect size, small enough to allow for a more personalized experience, but big enough to experience the music culture with others. Their menu features southern staples and classic American dishes.

Wilbur Theater

  • Historic performing arts theater that originally opened in 1915
  • Features basic concessions and a full bar
  • Comedy and music venue

The Wilbur Theater is located in the heart of Boston’s historic theater district. The capacity of the theater is 1,200, making it a smaller sized venue, which allows for great views from every seat and a more personal show experience. You’ll find A-list talent performing here, with past acts including Joel McHale, Jimmy Fallon and Bill Maher!

Travel with peace of mind. Travel WITH a security belt.
Active Roots Security Belt

Get your cash stashed with this awesome Pacsafe money belt. It will keep your valuables safe no matter where you go.

It looks exactly like a normal belt except for a SECRET interior pocket perfectly designed to hide a wad of cash or a passport copy. Never get caught with your pants down again! (Unless you want to.)

View on REI!

10 Other Awesome Things to do in Boston This Weekend

If you’re in Boston for a weekend here are a few more places we recommend checking out that’ll make your weekend as eventful as possible!

#1 – Explore Boston’s Museum of Fine Arts

The Museum of Fine Arts in Boston is the fifth largest museum in the United States. It has a comprehensive collection of more than 450,000 works of art. Peruse the museum and enjoy art collections for the Americas, Africa, Asia, Europe, and more!

Check out the “Garden of the Heart of Heaven,” a peaceful and picturesque Japanese garden. Walk around more than seventy species of plants and enjoy the meditative atmosphere. You could easily spend all day here, so if you’re spending 3 days in Boston or more, make sure to take your time exploring all the areas that interest you.

#2 – Wander Around Beautiful Beacon Hill

Beacon Hill is the area of Boston you see on postcards. With red brick mansions, cobblestones paths, gas street lamps, and tree-lined streets, Beacon Hill is a must-see area of the city. This historic district is filled with boutique shops, casual eateries, and cozy coffee shops.

Enjoy a peaceful stroll and admire the upscale Bostonian living. Make sure to check out Acorn Street, it is one of the most photogenic spots in Boston. This historic street is one of the very few streets in the U.S. with its original cobblestones still in place. You’ll feel like you’re stepping back into colonial times with a trip to this iconic Boston site.

#3 – Walk Along the Freedom Trail

Walk Along the Freedom Trail
Freedom Trail

Freedom Trail is a 2.5-mile-long path that winds through downtown Boston. It covers 16 locations significant to the history of the United States and is one of the most popular attractions in the city.

Follow the red line on the sidewalk to take your own self-guided tour of important American Revolution sites. The trail starts at the Boston Common, a large public park, and ends at the iconic Bunker Hill Monument.

#4 – Visit the Boston Tea Party Ships and Museum

Boston is one of the most important cities in American History. Relive the most important events leading up to the American Revolution at the Boston Tea Party Museum. Engage in interactive and informative exhibits alongside a fun cast of actors. This museum operates a little differently than other museums.

For 1-hour you’ll be guided by an 18th-century costumed host on a fully immersive tour. You’ll visit the ships and museum, watch a multi-sensory documentary, experience an interactive town meeting, and get a chance to dump tea bags into the harbor! This museum is designed to engage all ages and is fun for the whole family!

Book your Boston Tea Party tickets here!

IN A RUSH? THIS IS OUR FAVORITE HOSTEL IN BOSTON!

HI Boston

HI Boston is centrally located next to most of the city’s top attractions, including Boston Common and Chinatown.

  • $$
  • Free WiFi
  • Free Breakfast

#5 – Relax at The Boston Public Garden and Boston Common

Relax at The Boston Public Garden and Boston Common
Boston Public Garden

The Boston Public Garden is a large park nestled in the heart of the city. It was the first public botanical garden in the United States. Enjoy the lush Boston landscape and the social ambiance at this serene section of the city

Adjacent to this park is the Boston Common. We thought we’d include both areas, seeing as they’re directly next to each other and can easily be visited in one trip. The Boston Common is the oldest city park in the United States, dating from 1634!

This area of the city is a great place to recharge before continuing your weekend in Boston itinerary!

#6 – Step Back in Time with a Trip to the Paul Revere House

Step Back in Time with a Trip to the Paul Revere House
Paul Revere House

Built in 1680, the Paul Revere House is the oldest remaining building in downtown Boston. It belonged to American patriot, Paul Revere during the time of the American Revolution. This original 3-story house operates as a non-profit museum. For a small fee, guests can tour the house at their own pace.

This self-guided tour takes you through the life of the Revere family, Paul’s trade, and his involvement in the American Revolution. There is also an education and visitor center connected to the house for further learning. For history-lovers trying to decide what to see in Boston in 2 days, this stop is a must-see attraction!

#7 – Visit the Gravesites of Famous Americans at Granary Burying Ground>

Visit the Gravesites of Famous Americans at Granary Burying Ground
Granary Burying Ground

Filled with history, the Granary Burying Ground is Boston’s third-oldest cemetery, founded in 1660. This cemetery holds an estimated 5,000 people, including famous Bostonians and early Americans.

The most famous gravestones belong to Paul Revere, Samuel Adams, and John Hancock. Five victims of the Boston Massacre are also buried here as well as Benjamin Franklin’s parents. This cemetery sits quietly in the middle of the city, surrounded by tall buildings and busy streets. It’s located along the Freedom Trail and is free to enter.

#8 – Take a Boston Brewery Tour

Boston is famous for its craft beer scene, what better way to experience the local beer culture than on a brewery tour! There are several brewery tours in the city to choose from, but we recommend Harpoon Brewery and Beer Hall.

This brewery is located in Boston’s Seaport District and is the perfect place to enjoy beer with friends! Learn about the brewing process in Boston and enjoy a range of freshly-brewed Harpoon beers. This brewery is also well known for its large pretzels, which are made on site from the leftover yeast of beer brewing! Pair a pretzel with your pint at this fun Boston brewery!

#9 – Visit North End

The North End
North End

North End is Boston’s oldest neighborhood. This area of the city is also referred to as Boston’s Little Italy. Here you’ll find narrow streets lined with some of the city’s oldest buildings, and of course, lots of Italian restaurants and pastry shops!

The Freedom Trail passes this area of the city. This is the location where the famous “one if by land, and two if by sea,” signal was given to Paul Revere that launched his midnight ride (“The Redcoats are coming!”), and thus, the American Revolution! Walk the cobblestoned streets, admire the architecture, and take in the delicious aroma of Italian food!

#10 – Enjoy Some Fun in the Sun at The Lawn on D

The Lawn on D is an outdoor playland that’s fun for all ages! This Boston attraction is always buzzing with energy and a fun social atmosphere. There are large circular swings, lawn games, life-size checkers and chess sets, live music, and more!

This social hangout is a great place to meet new people. There are a wide variety of food trucks where you can enjoy a bite to eat, or grab a cold drink and relax on the lawn. Adults and kids will both enjoy this addition to their Boston weekend getaway.

Is This the Best Daypack EVER???
Osprey Daylite Plus

We’ve tested countless day packs over the years, and now we’ve found our absolute favourite: the traveller-approved Osprey Daylite Plus.

Want more deetz on why we love it so damn much? Then read our comprehensive review for the inside scoop!

View on Osprey View on REI

Boston Weekend Travel FAQs

Now that we’ve covered the Boston places to visit, we thought we’d add in a few more details about the city and answers to questions you might be asking yourself.

Boston Weekend Travel FAQs

Here are some of the most frequently asked questions.

Don’t Forget Your Boston Travel Insurance

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.

There’s one travel insurance provider The Broke Backpacker trusts for all his wildest shenanigans… World Nomads!

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. 😉

Final Thoughts on a Great Weekend in Boston

Boston is one of the oldest and most historic cities in the United States. Weekends are a great time to experience this city in high-drive! Whether you’re a nature-lover, history-buff, food fan, beer drinker, or sports enthusiast, you’ll find options to suit everyone’s preferences.

As one of New England’s most vibrant and scenic cities, countless visitors are drawn to Boston each year. It has all the components necessary to make for a memorable trip and is a city you’ll want to keep coming back to!

We hope this guide has helped you discover all the highlights of this east coast city. From its early American architecture to its rich culture to its charming scenery, you’ll find it all in Boston!


Thanks for reading – that was fun! 😀

We bring you epic FREE content!
Find out how YOU can help support us.

We’re a big site with a big team and this job isn’t always easy. But we do it because we love it – we love providing epic and free content. We love the knowledge that our content keeps you adventuring. We don’t ask for money, but if you’d like to find out how you can help the site in more organic ways, click the button below.
Thank you for your support 🙂


Bye for now, but not forever!

If you want MORE top-tier Broke Backpacker content like this, then sign up for our weekly newsletter below to get the latest and greatest!










    And for transparency’s sake, please know that some of the links in our content are affiliate links. That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!