Last updated on November 3rd, 2023
Looking for the best Boston 3 day itinerary? Here is everything you can do in Boston in 3 days.
Boston is one of the oldest (and most interesting) cities in the States. With top educational institutions, famous sports teams, and history galore, it’s no wonder Boston is a popular destination for travelers.
Understandably, the city can be overwhelming with all there is to do & see. So, I’m giving you the most exciting ways to spend 3 days in Boston.
You’ll learn all about what to see in Boston in 3 days, from museums to the best place to grab a lobster roll.
After reading this post, you’ll have the best Boston 3 day itinerary for the perfect weekend in Beantown.
This post is all about the best Boston 3 day itinerary.
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Best Time to Visit Boston
If you’ve heard anything about Boston, it’s probably that the winters are brutal. So, unless you can handle the intense cold, I would advise against visiting Boston during winter. However, you can still have loads of fun on a trip to Boston during the cold months.
The best time to visit Boston is May through October. However, I recommend visiting in late spring or mid-fall, as the temperature is cooler during these times. And during the spring, you can almost feel locals’ relief in the coming hotter months.
Summer in Boston is lovely because of the many outdoor activities like baseball games and concerts. However, keep in mind, many others are aware of this too. So, you can expect a swarm of visitors and higher hotel rates during the summer months.
Best Places to Stay in Boston
With Boston being a larger city, there are several places to stay in Boston. However, not all areas are created equal. Some neighborhoods are more dangerous than others, some spots extremely expensive, or just not in an ideal location for touring all the major sites.
I know what you’re thinking: ah, man, now I have to research the best (and safest) areas in Boston AND plan the whole trip. Where am I going to find the time to do all that?
Well, to save you the hassle & trouble, I’ve gone ahead and done the research for you.
Here are the best areas to stay in Boston.
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- Downtown & Waterfront area: Best for first-time visitors or anyone that wants to be close to Boston’s major attractions.
- South End, North End, Downtown, Chinatown, and Seaport District: Best neighborhoods for foodies.
- Kenmore Square and Allston/Brighton: Best neighborhoods for nightlife.
- Downtown & Waterfront area: Also an excellent area for families as the New England Aquarium, Children’s Museum, and more family-oriented attractions are all located in this part of town.
My Favorite Hotels in Boston:
Boston 3 Day Itinerary
Day 1 of 3 Days in Boston Itinerary
Hop-on Hop-off Trolley
On your first day in Boston, the first thing to do is ride the hop-on hop-off trolley. Now, I know what you’re thinking: really, isn’t that a super touristy thing to do?
The answer is yes, it’s a super touristy thing to do. However, you ARE a tourist, number 1. And number 2: this trolley is an excellent way to get a general lay of the land and learn about the city’s history.
You can grab your ticket here. Trust me, this is the best way to start your Boston trip.
Freedom Trail Tour
Next on your Boston itinerary, you MUST take a Freedom Trail tour. You can walk the trail by yourself if you want a free activity. Although, the guided tour is extra fun because you get the added perspective of the city’s historical spots from a professional tour guide.
Also, you can ask your local guide about the best places to eat or things happening in the city during your visit. If anyone knows, they know.
Here are some of the iconic sights you’ll see on the 2.5-mile Freedom Trail:
- Boston Common
- Park Street Church
- King’s Chapel & King’s Chapel Burying Ground
- Old Corner Bookstore
- Boston Massacre Site
Grab a Lobster Roll
Did you even go to Boston if you don’t eat a lobster roll?!
To prevent such a tragedy from happening, visit Yankee Lobster to taste one of the best lobster rolls Boston offers.
If you’re feeling extra hungry, get the jumbo lobster roll that comes with 1lb of delicious lobster and a side of fries. This is a monster meal, so only get it if you can handle it. (Or split it with someone).
Fenway Park
The last stop on day 1 is the famous baseball stadium, Fenway Park. As the oldest ballpark in Major League Baseball, Fenway Park is a major stop for sports fans.
Catching a game is one of the best ways to spend Friday night in Boston, even if you aren’t a baseball fan. So, if you’re visiting during baseball season, grab a ticket!
Visitors can tour the stadium, learn about its history, and even shop for souvenirs. Make sure you get a photo too! Tours usually last an hour and can be booked here.
Day 2 on the Best Boston Itinerary
Institute of Contemporary Art
First up, on day 2, visit the Institute of Contemporary Art (ICA). This is the perfect indoor activity if you’re trying to escape the scorching sun or dreadfully cold winters.
Art lovers and creatives alike will love ICA because it houses some of the most cutting-edge art in the world! With this wide array of work, visitors will likely be inspired while experiencing others’ work.
And even more exciting, you can shop for souvenirs in the gift shop & something to remember your visit. So, overall, I’d recommend planning to spend about 2-3 hours at the ICA.
Tickets are roughly $20/person. Students and seniors get in at a discounted price & all children get in free.
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Newbury Street
Newbury Street is an absolute MUST when visiting Boston. One of Boston’s top shopping, dining, and entertainment districts, Newbury Street, has hundreds of local eateries and shops.
Rumor has it this is one of the most expensive streets in the world.
So, naturally, you have to experience it for yourself. But don’t stay too long or you’ll spend all your money…(cue in the nervous laughter).
Spend your afternoon doing a little shopping, and then get a bite to eat afterward.
See a comedy show at Improv Asylum.
I love nothing better than spending an evening laughing at a comedy show. So, of course, I had to add the best comedy club in Boston to the itinerary, Improv Asylum.
Improv Asylum puts on shows that include pre-written sketches and hilarious improv on Thursday through Saturday nights. The club also hosts a special adults-only improv show at midnight on Saturdays.
This is a fun & unique way to end the night. You can check out their schedule and purchase tickets on their website.
Day 3 of Boston in 3 days
Boston Tea Party Museum & Ships
If you’re an American, you have most likely heard of the Boston Tea Party at least once in your life. And I’m sure it didn’t sound very interesting at that time. Trust me, I get it. 😅
But now you’re actually in the place it happened! Which is kinda cool. And the Boston Tea Party Museum & Ships is an excellent place to learn (or refresh your memory) about what happened all those years ago.
General admission tickets start at $32, but you can upgrade to the trolley package at $82. Tickets can be purchased here.
Go Whale Watching
Next, we’re headed to the sea! Boston is well-known as one of the best places to watch the whales migrate. So, if you visit anytime between May and October, you must go whale watching.
This Boston Whale Watching Cruise is the best in town! On the High-Speed Catamaran, you’ll have 3.5 hours to spot whales and even dolphins. And as we know, children love animals of all kinds, so this is an adventure the whole family will love.
Explore the Isabella Stewart Gardner Museum
Last but certainly not least is the beautiful Isabella Stewart Gardner Museum. This museum actually has a fascinating story. In 1990, two people dressed as Boston police officers stole 13 art pieces, making it the biggest art theft in history.
Sounds like something straight out of Ocean’s 11.
Besides this major art heist, the Isabella Stewart Gardner Museum is a fantastic art museum that houses European, Asian, and American art. The museum showcases a mix of paintings, sculptures, and more unique pieces that intrigue visitors.
Art lovers will certainly enjoy their time exploring this stop!
Summary: The Perfect Boston 3 Day Itinerary
Day 1
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- Ride the Hop-on, Hop-off Trolley
- Freedom Trail Tour
- Grab a Lobster Roll at Yankee Lobster
- Fenway Park – Book a Stadium Tour
Day 2
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- Visit the Institute of Contemporary Art
- Shop till you drop on Newbury Street
- Comedy show at Improv Asylum
Day 3
This post is all about the best Boston 3 day itinerary.
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