How to Spend 2 Days in Boston
Travel Itinerary
Itinerary Contents
Itinerary Introduction
Boston, Massachusetts, is a destination with something for everyone. History buffs can witness monuments dating as far back as the American revolution. Foodies can enjoy eating their weight in Italian food in the North End. And sports fans can catch a baseball game at America’s oldest stadium, Fenway Park. No matter what you’re looking for, it’s easy to fall in love with Boston. Photo credit to usmc0491 at pixabay.comUseful information about Boston
Best times to visit Boston
While Boston can be enjoyed any time of year, June through October is best. The winter months can be bitterly cold with plenty of snow, so avoid November through February to enjoy everything the city has to offer. April is also notoriously rainy, so be sure to pack an umbrella if you visit then. Springtime in Boston is gorgeous but can be a bit chilly. However, as Boston’s shoulder season, visiting between March and May likely means excellent hotel deals. Just be sure to pack a jacket. The high season in Boston coincided with the New England summer, where temperatures are typically in the 70s and 80s Fahrenheit. There are tons of things to do this time of year, from ball games to music festivals. Unfortunately, it is also the most expensive time to visit, so consider this in your budget.Getting around in Boston
Featuring 35 colleges and universities within city limits, Boston is a big city with a small college town feel. Strolling through Boston’s neighborhoods on foot is the best way to drink in all the culture and history this beautiful city has to offer. However, if you need to travel further than you prefer to walk, consider taking “the T.” The MBTA subway system is the oldest subway in the United States and extends throughout the city and far into neighboring towns. Locals call it the T, and subway passes are called CharlieCards and can be purchased from kiosks at every train station. At the time of writing, a one-way T ride costs $2.75 for most rides. Traffic throughout Boston is notoriously bad. As an old, organically built-up city, streets in Boston rarely follow a grid pattern. They are even less likely to be orientated by cardinal direction. So unless you are an extremely experienced city driver, avoid driving at all costs. And unless it’s raining, the T is preferable to taxis that get stuck in traffic.Tipping in Boston
As a U.S. city, tipping is expected for any service you receive. So be sure to tip at least 15%-20% at restaurants and at least $1.00 per drink at a bar. It’s also standard to tip 10%-15% for other services such as taxis and hairdressers.Where to stay in Boston
Many of Boston’s neighborhoods are great for travelers. Downtown is best for proximity to both tourist hot spots and the city’s financial district. Similarly, the Back Bay area is highly desirable for being both lively and centrally located. In addition, both Downtown and Back Bay are very well-situated for public transportation access. You may also want to consider the North End, Boston’s historically Italian neighborhood featuring quaint cobblestone streets and enticing eats. Finally, Beacon Hill is full of historical landmarks, including the Boston Common, and is another excellent pick. There are plenty of accommodation options, although hotels are typically the best way to go. The most important consideration when choosing your Boston jump-off point should be proximity to a T stop. Many suburbs are only accessible by the less-frequent commuter rail, making transportation around the city difficult.Boston - Travel Itinerary
Day 1
The History of Boston, Old and New
The Boston Freedom Trail
| Category | Price | Restrictions |
|---|---|---|
| Standard | 0.00 - 16.00 USD | |
| Students | 14.00 USD | |
| Kids | 8.00 USD | Under 12 |
| Seniors | 14.00 USD |
Faneuil Hall Marketplace
Notes
While Faneuil Hall is itself a stop along the Freedom Trail, exploring this massive marketplace requires some extra time. You may choose to visit on your walk or double back if you're part of a tour.
Travel time
0 hours 10 minutesUnion Oyster House
| Category | Price | Restrictions |
|---|---|---|
| Standard | 25.00 - 40.00 USD | Plus fee |
Notes
After all the walking and excitement of your morning, enjoy a nice sit-down lunch at this Boston landmark.
Getting there
From Faneuil Hall, the Union Oyster House is a short 3-minute walk via North St and Union St.
Travel time
0 hours 3 minutesThe Boston Common
| Category | Price | Restrictions |
|---|---|---|
| Standard | Free |
Notes
Enjoy a relaxing afternoon on the Boston Common before gearing up for an exciting night of baseball.
Getting there
From the Union Oyster House, the Boston Common is an easy 15-minute walk via Tremont St. Alternatively, you may choose to ride the MBTA Orange Line from Haymarket to Downtown Crossing for a 10-minute journey.
Travel time
0 hours 15 minutesBodega
| Category | Price | Restrictions |
|---|---|---|
| Standard | Free |
Notes
On your way to the ball game, consider stopping at this incredibly trendy hidden shop!
Getting there
To make this neat detour, Take the Green Line as you would to Fenway Park, using either the B, C, or D train, and get off at the Hynes Convention Center. Once you're done shopping, get back onto the T and continue onward to Kenmore.
Travel time
0 hours 15 minutesWatch the Red Sox at Fenway Park
| Category | Price | Restrictions |
|---|---|---|
| Standard | 20.00 - 225.00 USD | Plus fee |
Notes
Plan to arrive early, Fenway Park gates open a full 90 minutes before Red Sox games, and there is plenty of pre-game excitement you don't want to miss!
Getting there
To get to Fenway Park, especially on game days, it is highly recommended you take the T. From Boston Common, you will want to take the Green Line from Boylston to Kenmore. There are a few different Green Line trains, so be sure you take either the B, C, or D train, as the track splits and not all make it to Kenmore. Expect crowded trains full of excited Sox fans and avoid wearing New York Yankees paraphernalia unless you're looking for a fight.
Travel time
0 hours 30 minutesDay 2
Exploring Further into Boston's Neighborhoods
Harvard University Historical Tour
| Category | Price | Restrictions |
|---|---|---|
| Standard | Free |
Notes
Be sure to reserve a tour ahead of time on the Harvard University Visitor's Center Eventbrite page. Unfortunately, there is limited space available for the free student-led tours, and you don't want to miss out!
Getting there
Did you know that technically Harvard University is in Cambridge, MA? Fortunately, the Red Line will take you over the Charles River to Cambridge. From the Boston Common, the journey only takes around 10 minutes on the T. Regardless of where you begin; you will need to take the Red Line to the stop named Harvard.
The Garment District
| Category | Price | Restrictions |
|---|---|---|
| Standard | Free |
Notes
Be sure to grab some lunch in Harvard Square before setting off to the Garment District. You could easily spend all day in this massive store, and you certainly don't want to be hungry. Also, keep an eye out for another famous university, MIT, in this neighborhood.
Getting there
From Harvard University, the Garment District is 1.2 miles straight-shot down Broadway or Harvard St. On a nice day, walking is the best option. However, you may also choose to save 10-minutes by taking the Red Line to Kendall/MIT.
Travel time
0 hours 20 minutesNew England Aquarium
| Category | Price | Restrictions |
|---|---|---|
| Standard | 32.00 USD | |
| Members | 0.00 USD | |
| Kids | 23.00 USD | Under 11 |
| Seniors | 30.00 USD |
Getting there
Unfortunately, there are no direct train connections from Kendall/MIT to the New England Aquarium. To take the T, you will want to take the Red Line from Kendall/MIT to Park Street. Then you will walk approximately 7 minutes to the Government Center Blue Line Stop. Finally, take the Blue Line to the Aquarium stop. Alternatively, you may choose to take an Uber or taxi.
Travel time
0 hours 30 minutesBoston Duck Tours
| Category | Price | Restrictions |
|---|---|---|
| Standard | 45.99 USD | |
| Kids | 30.99 USD | Under 11 |
| Seniors | 36.99 USD |
Getting there
Boston Duck Tours has starting points across the city. One such ticket booth and meeting point is conveniently located just outside the Aquarium.
Improv Asylum
| Category | Price | Restrictions |
|---|---|---|
| Standard | 29.00 - 35.00 USD | |
| Group | 0.00 USD |
Notes
Before the show, follow your nose to find some delicious Italian food for dinner in the nearby North End. There are countless family-owned restaurants in the area that are sure to knock your Sox off!
Getting there
From the New England Aquarium, Improv Asylum is an easy half-mile walk via Cross St.
Travel time
0 hours 10 minutesModern Pastry
| Category | Price | Restrictions |
|---|---|---|
| Standard | 4.50 - 5.50 USD |
Notes
Why not end your Boston experience on a sweet note with a cannoli from Modern Pastry?
Getting there
After a show at the Improv Asylum, dessert is just a few doors down! Take a left onto Hanover St, and Modern Pastry will be a couple of storefronts down on your right.
Travel time
0 hours 2 minutesAbout the author
I am an avid writer, blogger, and professional scuba divemaster. A nomad at heart, I spend my time bouncing between the world’s coolest destinations while calling a ridiculously oversized backpack home. I'm thrilled to be here at MapADay to share my travel insights.
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