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A Weekend in Boston: The Ultimate 3 Day Itinerary

Looking to spend a weekend in Boston?

Given the popularity of this bustling city, we’re not surprised.

For history lovers, Boston offers a gold mine of revolutionary tales.

Just stand on the corner of King Street gazing up at the Old State House, and it’s surprisingly easy to transport yourself back to the day of the Boston Massacre and other historical moments in our country’s history.

Weekend in Boston

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Whether you’re keen to visit Boston’s many historical sites, or you’re just pining after the best lobster roll in town though, this guide’s got you covered.

Read on to find out about all the unforgettable things to do during a weekend in Boston — we dare you to try them all!

Best Time to Visit Boston

The best time to book a trip to Boston falls between June through October.

The fall season is particularly beautiful in New England, so this is an ideal time to take a road trip and enjoy the colorful foliage.

The warm weather during the summer and early fall seasons also bring plenty of opportunities for outdoor concerts, baseball games, or even just hanging out at the park.

If you’re looking to avoid the tourist season though (which includes higher hotel rates and bigger crowds), we also recommend visiting Boston during the holiday season.

The city makes sure to bust out its best seasonal decor, and overall there’s just a special festive feeling when visiting Boston this time of the year.

Weekend in Boston

How to Get Around During a Weekend in Boston

While you’re planning your trip, you might be wondering what the best way to get around Boston is.

When we traveled here, we relied heavily on Uber/Lyft for a few reasons.

The number one reason we used Uber/Lyft is because it was convenient.

Though we did drive our car to Boston, we would NOT recommend driving around to all the different spots in this guide.

We learned this lesson the hard way when we tried to drive to Quincy Market when we first reached Boston and realized parking would be $40 in the only garage we could find with open spots!

Parking in Boston is expensive and time consuming, so to maximize your time and your dollar we recommend using ride sharing services like Uber or Lyft.

Another, even more economical option however is Boston’s subway (known by locals as the “T”). One way, the T only costs $2.25 with a Charlie Ticket (credit card like pass that you can load up ahead of time with money for the subway).

You can also take Boston’s many buses around the city as well.

Related: 9 Unforgettable Things to Do in Newport RI

Best Place to Stay in Boston

Best Place to Stay in Boston

Before you start your weekend in Boston, you’re first step is likely selecting accommodations for your trip.

We recommend staying at the AC Boston Downtown for a few reasons.

First of all, this Marriott brand hotel is incredibly located.

Literally minutes away from some of the best Boston attractions, you really can’t go wrong.

The rooms at the AC Boston Downtown are extremely well kept (no carpet either, yay!), include smart TVs, and overall are very modern and comfortable.

The hotel also offers a delicious European style breakfast with assorted meats and cheeses, as well as an on-site restaurant.

A Weekend in Boston: The Ultimate 3 Day Itinerary

Day 1 Weekend in Boston Itinerary

Quincy Market

Start your first morning in Boston off with a visit to the charming, historic Quincy Market.

Offering a number of unique shops to explore and at least a few ongoing street performances, it’s best to hit up this popular Boston attraction before the midday crowds arrive.

Speaking of street performances, these aren’t the cheesy tricks and tourist traps you might be used to seeing if you’ve been to New York.

You might just watch a man escape from a straightjacket while tied upside down, or even listen to your favorite pop tunes during an amazing violin performance.

You never know what you’ll find here, so take a moment to soak it all in.

Aside from the market itself, the surrounding mall area features traditional retailers and some high end shops.

Make sure you grab a buttery pastry and some coffee inside the marketplace though before venturing outdoors.

Weekend in Boston

Faneuil Hall

During your visit to Quincy Market, it’s pretty hard to miss Faneuil Hall.

Operated as both a visitor center and historic site, this hall is special because it is where many of the meetings were held in the 1700s to discuss British policy.

A number of famous historical figures such as Samuel Adams and other Sons of Liberty gave speeches here in protest of “taxation without representation” and other grievances preceding the Revolutionary War.

It’s definitely something worth checking out while you’re in Boston.

The history is so rich in this city, that you just can’t go wrong with diving right into it and learning more about the past.

Weekend in Boston

Freedom Trail Guided Tour

Start your afternoon off with a bit of Boston history and take the Reverse Walk Into History tour starting at Faneuil Hall.

You’ll visit all sorts of historic sites on The Freedom Trail, including the site of the Boston Massacre, Old State House, King’s Chapel Burying Ground, Massachusetts State House, Boston Common, and more.

For only $14 per adult, this 90 minute guided walking tour really is worth both your time and money.

Related: 7 Things to Do in the Catskills This Weekend

Lunch at James Hook & Co.

If you’re looking to try out the local fare without the steep price tag typically associated with fresh seafood, you absolutely must pay a visit to James Hook + Co. for one of their mouthwatering lobster rolls.

There’s a reason why they won Best of Boston in 2013, so don’t be put off by the modest building.

Step inside, take a look at all the fresh food, order yourself a lobster roll, and smile knowing that you’re eating one of the best local dishes in town!

Boston Harbor

Explore the Waterfront

You can’t visit Boston and miss out on exploring the beautiful waterfront.

Spend the rest of your day perusing the views, leisurely shopping, or stopping into a few museums.

If you just want to walk off your lunch, ask your driver to take you to Harborwalk. This path features almost 40 miles of pedestrian and bike friendly public access at Boston’s waters edge.

You can also check out highlights like the USS Constitution Museum, the Institute of Contemporary Art, and the Boston Tea Party Ships & Museum.

There’s plenty of cafes to explore in the area when dinnertime hits, and make sure you hit up Lucky’s Lounge afterwards for an evening drink and some classy live music.

New England Aquarium

Day 2 Weekend in Boston Itinerary

Boston Brunch & New England Aquarium

Head back down to the waterfront this morning for brunch and a trip to the New England Aquarium.

Make sure you have your Boston City Pass at the ready, as you’ll save 46% on Boston’s top four attractions (trust me, you want this).

Speaking of the New England Aquarium though, this is a fun attraction for both kids and adults alike.

The aquarium is pretty sizable (though of course not as big as the largest aquarium in the world!), and even features realistic coral reefs and an awesome open tank exhibit at the top of the building.

Plus it’s part of the Boston City Pass anyways, so why not?

Once you’ve finished up at the aquarium, head to brunch (or do this beforehand if you’re hungry).

Theo’s Cozy Corner, North Street Grille, and Caffé Vittoria (renowned as the first Italian cafe in Boston) are all popular locations nearby.

Paul Revere House

During a weekend in Boston, you simply can’t miss out on touring the famous Paul Revere house.

It’s a relatively short tour, so this is a great option to learn more about America’s revolutionary history without having to dedicate too much of your trip to it.

You’ll also be surprised at some of the interesting things to learn here, like the fact that Paul Revere was not actually the only rider on that fateful night.

He didn’t even become a household name until after his death, due to a poem by Henry Wadsworth Longfellow, which excluded the name of the other rider, William Dawes.

It’s pretty cool experience, and the entrance fees are very reasonable!

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Boston North End

Little Italy

While you’re in the neighborhood, make sure to grab a bite to eat in Boston’s Little Italy.

There are over 80 Italian restaurants and patisseries located along the beautiful North End cobblestone streets, so you’re bound to find something that appeals to your appetite.

Boston Public Market

Round off the day with a trip to the Boston Public Market.

This indoor market boasts 35 New England artisans and food vendors, and overall is a great place to explore some unique, locally made goods.

It’s quite a different experience than Quincy Market, which borders on a bit touristy, so you’ll definitely want to check this one out.

Skywalk Observatory

Day 3 Weekend in Boston Itinerary

Skywalk Observatory

This morning, make your way to the Skywalk Observatory.

Though you won’t spend a ton of time at this tourist attraction, this is a fun way to see Boston from above and get some great Insta-worthy travel shots.

On a clear day, you can even see up to 100 miles away from the observatory!

Boston Museum of Fine Arts

Next stop?

The Boston Museum of Fine Arts.

Whether you’re a museum person or not, Boston’s collection of historical objects from such a vast variety of time periods is almost unfathomable until you see it yourself.

Featuring objects from over 3,000 years in the Americas alone, the Boston MFA does not disappoint.

You can spend an entire afternoon here, especially if you’re a history lover, so make sure you block off a decent amount of time.

The museum even has an extensive collection of ancient Egyptian mummies, which is pretty incredible to see for yourself.

There’s so many collections of different historical artifacts from all over the world, we didn’t even make it through probably half of what was on display.

Not to mention, the museum has many traveling exhibits that are on display for a limited time as well.

Overall, it’s definitely worth your time.

Related: 13 Short Inspirational Quotes That Will Make You Want to Travel

Fenway Park

What’s a trip to Boston without a tour of the historic Fenway Park?

Whether you’re a fan of the team or not, you’re bound to enjoy learning more about the Boston Red Sox history and some of the iconic moments that have occurred at this famous stadium.

This is an absolute must for all sports lovers!

Weekend in Boston Final Thoughts

Overall, a trip to Boston is not to be overlooked.

This historic city has something to offer for almost anyone and is especially rich in museums, food, and culture.

We’d 10/10 recommend booking a trip and starting to plan your next adventure today.

What’s your perfect weekend in Boston look like? What are your favorite things to do in Boston this weekend?

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Holly

Holly is a millennial travel and lifestyle writer based in New York. With ten years of experience in digital publishing and photography starting with her work writing for College Fashionista and Her Campus at Ithaca College, Holly has been featured in publications such as Southern Living and Lonely Planet. She enjoys sharing her travel expertise as well as lifestyle inspiration in categories such as home décor, DIY beauty, and fashion. More importantly though, Holly is a true Hufflepuff, and her Starbucks order forever remains a grande Iced Sweet Cream Cold Brew. When she's not writing or editing photos for this site, you can find her reading anything in the Sarah J. Maas universe or cuddling with her chihuahua x pomeranian pup Pixie.