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This blog post has been a long time coming. For readers who’ve followed my blogging journey, I began my travel blogging journey when I lived in Boston!
I’m so excited to share this 2 day Boston itinerary with you. When my parents from Australia, I got a chance to play tourist with them and show them around my home city.
This 2 day Boston itinerary is for first-time visitors to Boston who want to see the best that Boston has to offer without feeling exhausted at the end of it
Why visit Boston
I’m not a massive history buff, but it would be wrong of me to write about Boston without mentioning that this city plays a big part in the beginnings of US history.
After all, Boston is where the English (fleeing religious persecution) settled in 1630.
This makes Boston not only a place of historic significance but also a place filled with historical buildings!
Boston isn’t all history though. It’s also home to Fenway Park, the famous baseball park which is home to the Boston Red Sox.
But if you’re not a sports fan or a history buff, is Boston still interesting?
As a fellow non-sports fan and non-history buff, I’m here to say a resounding yes!
Boston is an incredibly charming city and a fun place to spend a weekend!
How to get around Boston
The best way to see Boston if via train, known locally as the “T”.
You can get what is known as Charlie Card, which is a reusable metro/ train card that you can load cash on and tap any time you see public transport in Boston. You can get a Charlie Card from train stations that have a kiosk – just ask the friendly staff at the station.
Each trip you touch on costs $2.25 and the Charlie Card is free to get.
Alternatively, most of Boston’s inner-city tourist sites are walking distance to each other, so while having a Charlie Card is helpful, depending on where you’re staying you might be get away with walking everywhere.
For my friends who aren’t fans of public transport or who can’t walk long distances, Uber is a great alternative. Boston also has Uber pool, which can be similarly priced to taking the train.
For my road trippin’ friends: Boston is also a great city to include on an East Coast road trip, so while you might not use your car to explore Boston, you certainly will need one to see more of New England!
2 days in Boston itinerary
After having lived in Boston for 2 years, I put together this itinerary for first-time visitors (I actually took my parents around to these places when they visited from Australia!)
If this is your first time in Boston, read on my friends!
Day 1: Central Boston
- Beacon Hill
- Boston Commons
- Boston Public Gardens
- Massachusetts State House
- Boston Public Library
- Newbury Street
Beacon Hill is one of Boston’s most charming suburbs. Here the streets are lined with brick, and the buildings are federal style and victorian brick row houses.
Every time I visited Beacon Hill, I had dreams of owning a home here (yep, I’ll be dreaming for a long time!)
I recommend starting with breakfast or coffee at Tatte (which is a Boston founded cafe chain) before exploring the historic streets of Beacon Hill.
Must see in Beacon Hill:
- Brunch at Tatte
- Main Street of Beacon Hill which is Charles Street
- Make sure you go for a wander through the surrounding streets, especially Acorn Street which is known for being one of the most photographed streets in Boston!
How to get to Beacon Hill: Take the T (train) to Charles MGH station which is on the Red Line and walk 2 minutes down to Charles St.
Boston Common and Boston Public Gardens
These neighboring park areas are a short walk from Beacon Hill (just walk down Charles St)
When I lived in Boston, the Boston Public Gardens was my favorite place to sit on a sunny day with a good book. Both these parks are worth a visit, and you can see tourists and locals alike enjoying the outdoors.
Must see at Boston Public Gardens
- Lagoon bridge, a picturesque bridge The Pond where you can ride on swan boats
- Make Way for Ducklings statues (which are often dressed up depending on the season / if there are special events on at the time!)
Must see at Boston Common
- The frog pond (which becomes an ice skating rink during the winter months)
- Parkman Bandstand
- Various monuments + a historical burying ground
Massachusetts State House
The Massachusetts State House is iconic to the Boston skyline, because of its distinctive gold dome.
I took my parents here when they visited Boston and we went on one of their free tours. Tours at the Massachusetts State House happen on weekdays from 10 am to 3:30 pm.
The tour covers the history of the Massachusetts State House as well as the general political history of Massachusetts.
Make sure you check out the inside of the dome while you’re there!
Boston Public Library
Boston Public Library is one of my favorite places in Boston. This is my favorite place to bring visitors, especially if they haven’t seen older libraries before. Make sure you check out the reading room for its iconic green lamps.
There’s also a beautiful courtyard that is a great place to enjoy the sunshine.
During the week there are many people who sit here and enjoy lunch.
I haven’t had a chance to (yet) but you can also go on one of their free library tours too, which covers the architecture of the library.
If you love shopping, Newbury Street is the perfect place to go. This street is lined with 19th-century brownstones which today are filled with boutiques, shops, and restaurants.
The shops are a mixture of high street chain stores, boutiques and high-end fashion designers. Honestly no matter your style (or shopping preference) you’re bound to find something you like here.
And if you don’t like shopping, this is a beautiful street to visit, just for the buildings!
Day 2: Cambridge, baseball, history, and art!
Breakfast at the Friendly Toast in Cambridge
If Tatte in Beacon Hill was on the fancy side for you, then you might enjoy the Friendly Toast. This diner has some of the best American diner breakfast in Boston.
The Friendly Toast gets really busy, especially on the weekends – but it’s worth the wait! Make sure you check out their website to join the virtual waitlist (so you don’t need to wait there!)
Visit MIT / Harvard
Boston is best known for some of the best colleges in the US, and most famously for Harvard and MIT.
You can even take a student-led historical tour of Harvard, which is free! I’d recommend this unless you know exactly what you want to see, otherwise, you end up roaming the campus, not really sure what you’re looking at!
MIT also offers tours to the public during the week or if a tour doesn’t sound that exciting, there’s also the MIT museum.
I’ve visited this on a spare afternoon (because why not?!) Being MIT, the museum has a technology focus, but it’s definitely worth a visit for my fellow nerdy readers. Entry is $10 for adults, $5 for students/ youth/children or free for MIT cardholders.
For the afternoon, I’d recommend choosing one of the following…
For baseball or sports fanatics, and a visit to Fenway Park is a must.
The best way to see Fenway park is at a game or if you’re visiting during the off-season, you can actually take an official tour of Fenway Park.
Isabella Stewart Gardener Museum
Isabella Stewart Gardener Museum is named after Isabella Stewart Gardener, an enthusiastic art collector who left behind her artwork to be displayed exactly as she left it.
What makes this museum so renowned is the infamous art heist that took place here in 1990 where thieves posing as the police gained entry. The works were never recovered, and because Gardener had stated in her will that nothing be moved, you can still see the empty spots where the artwork was.
Despite the museum’s loss, there is still plenty to see.
There is also a beautiful garden section in the middle of the museum and I 100% think it’s worth a visit even if you’re not a huge art buff. The free tour is informative and gives a thorough history of Isabella Stewart Gardener and the museum.
Psst: if you wear Red Sox gear you get a $2 discount or visit on your birthday for free!
Walk the Freedom Trail
The freedom trail is probably one of Boston’s most famous “things to do”. I’d only recommend it if you’re interested in sites of historical significance – otherwise, it can be a tad boring 😉
This 2.5-mile-long trail passes 16 sites of historical significance to the united states and takes approximately 1.5 – 2 hrs to complete (depending on how long you stop at each site)
Best time to visit Boston
Having lived in Boston, it’s hard to pick a month as the best time of year to visit Boston.
Boston is genuinely beautiful throughout all the seasons, and if you don’t have flexible travel plans you’re bound to have a fantastic time.
During summer, the sun is shining and people are strolling through the park. Fall is especially beautiful in New England for the golden-tinged foliage. Winter is strangely magical (though cold) when the charming suburbs are covered in a blanket of white.
But if I was forced to pick a season? I’d 100% say fall in Boston is the most beautiful.
Temperatures are mild, not too cold and not too hot, and nothing beats sipping a pumpkin spiced latte while enjoying the beautiful golden colored leaves.
So there you have it! My 2 day Boston itinerary.
I hope you find this 2 day Boston itinerary helpful for planning your trip.
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