Solo Travel Boston: Your Ultimate Weekend Guide

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Note: This is a guest post written by the lovely Kylee over at Passports and Preemies! Her solo weekend tips for Boston should help you all have a wonderful adventure in this historic American city. Happy reading!

Boston is a city rich in culture and history. Dating back to 1630, the capital of Massachusetts has played a crucial roll in American history.

Furthermore, Boston is where Benjamin Franklin attended school, where the Boston Tea Party protest occurred, where the Boston Massacre took place, and much more.

Without the city of Boston, the US wouldn’t be what it is today.

Currently, Boston is a coastal city brimming with character and charm. The city boasts world-class restaurants and has opulent buildings adorning its cobbled streets. It’s a place where old history meets new modern times

Ultimately, Boston is an overall fun and energetic city fit for a solo traveler.

Solo Travel Boston: Great for Any Time of Year!

Boston experiences all four seasons throughout the year, with a particularly long winter. With each season offering something special there is truly no bad time to visit Massachusetts.  

In the winter expect freezing cold weather with white snow covered streets. Spring brings cherry blossoms galore, framing iconic brick houses in historic neighborhoods. Summertime you can find yourself cruising by kayak along the Charles River, basking in the heat of the summer sun. And in fall find yourself surrounded by the wildly popular New England fall foliage.

With each season offering something different there are plenty of reasons to want to visit Boston year round. And in a walking city, there’s truly no better place to be as a solo traveler.

Solo Travel Boston: Planning Before You Go

1. Train Transportation

Boston is a completely walkable city, but when needed there is a cheap and expansive train system that weaves throughout the city referred to as the “T”.  

To ride the T you must purchase a CharlieTicket, which you can find at every train station.  The ride will cost $2.75/way or if you plan on taking the T multiple times in one day you can buy a day pass for $12.  

However, if you plan on staying for longer than a weekend a one week Charlie pass will set you back a mere $21.25.

When it comes to navigating the T, you may be overwhelmed at first.  With five different “lines” to figure out, there are maps in each train station showing you the way.  Or even easier, download the free “Transit” app for directions.  Simply put in where you’re leaving from, where you’re going to, and the app will tell you how to get to your destination the quickest and which lines to get on and off of. 

 The train also services the Boston Logan International Airport, so if you’re arriving by air you can easily take a free bus that will but you to the red line or the blue line to get into town.

If you aren’t keen on taking public transportation both Uber and Lyft service Boston.

Want More? Check out Lonely Planet’s Guide to Boston

2. Where to Stay Traveling to Boston Alone

Boston covers approximately 90 square miles and claims at least 22 different neighborhoods. 

With each neighborhood offering something different there are plenty of places to choose from when planning your travels.  From historic neighborhoods to newer neighborhoods, and everything in between, there’s something that will suite everyone’s needs.

If you’re coming to Boston to learn about the historic side of the city, Beacon Hill or the North End may be for you.  Beacon Hill is where you’ll find the iconic Federal and Victorian brick row houses and the picturesque Acorn Street.  

In the North End you’ll get a taste if Italy plus find yourself surrounded by some of Boston’s oldest buildings.  

If you’re looking for a more energetic part of the city, downtown Boston or the Fenway neighborhood is where you’ll want to be.  Downtown you’ll be surrounded by skyscrapers, bars, and restaurants; finding yourself near many historic sites while in the middle of the Financial Center.  And if sports are your thing, Fenway is home to Red Sox baseball and also a neighborhood brimming with bars.  

For a “fancy” taste of Boston, opt for the iconic Back Bay.  Here is where you’ll find Boston’s “Rodeo Drive” – Newbury Street – plus high-end restaurants and cocktail lounges.  

And lastly, if you want to get a feel for the “newer” side of the city, a stay in Seaport District is where you’ll want to be.  

But no matter which neighborhood you choose, walking or taking the train between each is easy and seamless, allowing you to explore the many different facets of Boston.

Ready to Go? Book Your Accommodation in Boston

Best Things to Do in Boston Alone

Day 1: Learning Boston’s History

During day one in Boston, you will start your day by getting a feel for American history by walking the Freedom Trail.  The Freedom Trail is 2.5 miles long, running from Beacon Hill to Charlestown.  

While free tours are offered through Free Tours by Foot, if you prefer to go at it alone, The Freedom Trail is a great resource.  Make sure to come hungry.  Halfway through the Freedom Trail you’ll come to Faneuil Hall Marketplace, which used to be an open forum-meeting hall.  Now you can find the Quincy Market here full of shops, bakeries, and restaurants.  Depending on the weather you can choose to dine either inside or outside, get takeaway or sit and enjoy your meal.  

(Please note that you can only stop to enjoy food at Quincy Market if you’re choosing to go at the Freedom Trail alone.  If you’ve chosen to take a tour you won’t have time to stop and eat).

Once you’ve seen the 16 sites on the Freedom Trail, head back to Beacon Hill, where you began, to enjoy one of the most picturesque neighborhoods in all of Boston. Visit Acorn Street, one of the most photographed streets in America (and for good reason) or boutique shop along Charles Street.  If the weather permits walk along the Charles River Esplanade or relax in the oldest park in America – Boston Common, dating back to 1634.

Once nighttime rolls around make your way to Boston’s “Little Italy” – the North End.  Inhabited since 1630, the North End is Boston’s oldest residential community.  Here you’ll find Italian restaurants lining the narrow streets, usually with long lines of customers hoping to get in.  

If you’re in the mood for Italian, head to Pomodoro or if you’re in the market for seafood, particularly a famed lobster roll, head to Neptune Oyster.  Both restaurants don’t take reservations and usually have a line, but both restaurants are worth waiting in line for.

Day 2: Exploring the In’s and Out’s of Boston

On your second day in Boston start your day early with brunch at The Friendly Toast in Back Bay. Enjoy Bloody Mary flights, mimosa flights, and items ranging from benedicts and omelets all the way to French toast and pancakes served in a hip, diner-like setting.

In the afternoon set out to see even more that Boston has to offer.  

If you like shopping head to Back Bay to shop along the expensive Newbury Street.  If you like beer perhaps head to Samuel Adams Brewery to take a tour.  If you like sports and you’re in town for a Red Sox game, I’d highly recommend heading to Fenway Park to see the game!  Or if you’d like to see a newer side of Boston, head to Seaport.  Here hang out on the rooftop of the Envoy Hotel (closed certain times of the year, make sure to call ahead); or grab a cocktail at the menu-less cocktail lounge – Drink.

If you’ve seen enough of Boston, take a quick and easy day trip up to Cambridge to tour Harvard University.  Taking the red line from Boston will drop you off smack in the middle of Harvard.  Go on a historic, student-led, tour of the University or explore alone.  Either way there are tons of bars and restaurants around the University and in Cambridge once you’re done exploring Harvard.

End your last night in Boston in the South End neighborhood at Beehive.  A top-notch restaurant with a lively atmosphere and bohemian vibes; plus live music each and every night.  Immersing yourself in the great atmosphere and live music, you’ll forget that you’re solo!

With that, a weekend solo in Boston comes to an end.  If you’re lucky enough to stay longer, there are still tons of neighborhood gems left to explore.  Or get out of town entirely!  Head to Spooky Salem and learn all about the witch trials. Rent a car and head south to the Cape for a stay in Provincetown.  Or head to Newport in Rhode Island to visit the sprawling Glided Age mansions!

No matter what the weekend brings, there’s so much to learn, experience, and enjoy in Boston.

Explore Outside of Boston: Get Your Boston Guide

I hope you all enjoyed reading this guest post! What other suggestions would you add? What are your favorite things to do in Boston alone? Have you ever spent a weekend in Boston?

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