2 Days in Boston

Travel Itinerary

0 ratings

Alex Dryjowicz
Itinerary by: Alex Dryjowicz
15 days ago
Travel Writer
Duration: 2 days

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. Getting Around 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. 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. What Time of Year is Best 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. Tipping Customs 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. Photo credit to usmc0491 at pixabay.com

Day 1

The History of Boston, Old and New

On your first day in Boston, you will get your bearings while strolling around to the most famous destinations in the city. After a day full of history, you will head to Fenway Park for a thrilling night of baseball!
09:00 - 11:00
The Boston Freedom Trail
139 Tremont St, Boston, MA 02108, USA
Start your day by taking in the history of Boston. This 2.5-mile walk takes you from Boston Common in downtown Boston all the way through North End to the Bunker Hill monument located in Charlestown. Along the way, you will stop by locations of significance in the history of the United States. You can walk along the brick path of the Freedom Trail for free, or buy a ticket for a scheduled tour. Some of the stops along the route have admissions fees if you wish to go inside. These are not included with your tour ticket. Photo credit to BookBabe on pixabay.com
Article By: Alex Dryjowicz
Standard 0.00 - 16.00 USD
Students 14.00 USD
Kids 8.00 USD Under 12
Seniors 14.00 USD

11:15 - 12:15
Faneuil Hall Marketplace
4 S Market St, Boston, MA 02109, USA
Centrally located in downtown Boston is the Faneuil Hall Marketplace. The marketplace is made up out of Faneuil Hall, North Market, Quincy Market, and South Market. This festival marketplace is comprised of more than a hundred different shops, merchant carts, and restaurants. The center building, Quincy Market is a great lunch & meeting spot, offering food from all over the world. During the summer months, you can find some of the best street performers here delivering local entertainment. We advise you to allow yourself an hour or two to browse the different shops and stalls. Photo credit to user ID-12019 on pixabay.com
Article By: Alex Dryjowicz

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 minutes
12:30 - 14:00
Union Oyster House
41 Union St, Boston, MA 02108, USA
A trip to Boston is incomplete without oysters, and what better place than the Union Oyster House. Established in 1826, the Union Oyster House is not only the oldest restaurant in Boston but one of the oldest in the entire United States! The restaurant has also served its share of historical figures, from Daniel Webster to John F. Kennedy. Beyond being a national landmark, the Union Oyster House serves up some delicious seafood and is conveniently located a three-minute walk from Faneuil Hall. Photo credit to photo-graphe at pixabay.com
Article By: Alex Dryjowicz
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 minutes
14:15 - 16:15
The Boston Common
139 Tremont St, Boston, MA 02108, USA
Established in 1634 and older than the United States itself, the Boston Common is the oldest city park in the country. Also, a stop along the Freedom Trail, you could easily spend all day in this gorgeous 44-acre park. From picnicking in the grass or watching free Shakespeare performances, splashing in the spray park or renting a swan boat, there is something for everyone. While you're here, be sure to check out the famous Make Way for Ducklings Statue near the corner of Beacon and Charles. Photo credit to user12019 at pixabay.com
Article By: Alex Dryjowicz
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 minutes
16:30 - 17:00
Bodega
6 Clearway St, Boston, MA 02115, USA
Looking for the hottest sneakers and streetwear? Bodega has you covered. This secret shop is well-disguised inside a generic convenience store. Believe it or not, you enter this high-end retail haven via a fake Snapple machine! Once inside, you will find the best curation of sneakers, clothing, and accessories in the city. Items can be a bit pricey, but everything is high-quality, or you can window-shop for free. So whether you live for fashion or are just curious about the concept, Bodega is a must-see. Photo credit Danilo Capece on unsplash.com
Article By: Alex Dryjowicz
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 minutes
17:30 - 22:00
Watch the Red Sox at Fenway Park
4 Jersey St, Boston, MA 02215, USA
Fenway Park is a must-see for any visitor and baseball fanatic. Being the oldest and perhaps most loved baseball stadium in Major League Baseball, it is also the home to the Boston Red Sox. Prepare to spend about half a day if attending a game. If the Sox aren't in town, tours of the park are also available. Fenway Park is easily reachable by means of public transportation, which is what we recommend as parking can be a bit of a nightmare and costly. Ticket prices are dependent on which team they are playing against and preferred seating. Snacks and beverages come at additional costs. Photo credit to GregSabin at pixabay.com
Article By: Alex Dryjowicz
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 minutes

Day 2

Exploring Further into Boston's Neighborhoods

On your second day in Boston, we go a bit deeper into what the city has to offer. You will start your day rubbing elbows with the nation's brightest at Harvard and end with the best cannoli in the city at Modern Pastry.
11:00 - 12:00
Harvard University Historical Tour
1350 Massachusetts Ave, Cambridge, MA 02138, USA
Ever wonder what it's like to live the Ivy League life? This free Harvard campus tour starts at the Smith Campus Center Welcome Pavillion and ends in the famous Harvard Yard park. Current Harvard students give these tours, so you're sure to be rubbing elbows with the best and brightest of the next generation. Your student guide will take you around campus and tell you about the historical significance of your surroundings, as well as their personal experiences attending the most famous school on Earth. Virtual tours are also available, and additional in-person tour options are offered for a fee from private companies. Photo credit to user12019 at pixabay.com
Article By: Alex Dryjowicz
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.

13:00 - 14:00
The Garment District
200 Broadway, Cambridge, MA 02139, USA
Move over NYC, Boston is stylin'! The Garment District isn't a district but a massive alternative department store full of unique finds. From their 1980s beginnings as an offshoot of the Harbor Textile Waste Co., The Garment District has specialized in recycled clothing and "green" fashion. Shoppers who live for the hunt will love the "By The Pound" section, where they dump an unsorted 850lb bale of clothing every day. You never know what you might find in the pit, but whatever treasures you come out with cost only $2.00 per pound. The rest of the shop is more organized but just as exciting with vintage finds, costumes, shoes, and accessories. Photo credit to DWilliam at pixabay.com
Article By: Alex Dryjowicz
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 minutes
14:30 - 16:00
New England Aquarium
1 Central Wharf, Boston, MA 02110, USA
Serving more than 1.3 million visitors annually, the New England Aquarium is a must-see Boston landmark. Only steps away from the historic Faneuil Hall Marketplace, you can enjoy the aquarium rain or shine. Featuring an impressive four-story giant ocean tank, three species of penguins, and some adorable sea lions, the New England Aquarium has something for everyone. The aquarium is also home to the Simons Theatre, an IMAX theater showing impressive nature films on a six-story high projection screen. IMAX tickets cost around $10 and can be combined with an Aquarium ticket for a discount. Photo credit to LopesTBM at pixabay.com
Article By: Alex Dryjowicz
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 minutes
16:00 - 17:30
Boston Duck Tours
1 Central Wharf, Boston, MA 02110, USA
Is it a bus? Is it a boat? It's both! On this tour of Boston, you travel in style on a renovated World War Two amphibious vehicle that takes you through some of Boston's oldest neighborhoods, as well as down the Charles River for some spectacular views of the city. While a bit touristy, this comprehensive tour is a ton of fun and perfect for visitors new to Boston. Your Boston Duck Tour can begin from several convenient locations across the city, including next door to the New England Aquarium. So buckle up and enjoy this unique city tour with your very own ConDUCKtor! Photo credit to Romanbakin at pixabay.com
Article By: Alex Dryjowicz
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.

19:30 - 21:30
Improv Asylum
216 Hanover St, Boston, MA 02113, USA
Improv Asylum is Boston's premier comedy and sketch show, guaranteed to make you keel over with laughter. An installation for over 20 years, Improv Asylum's Main Stage show is a can't miss. However, they also host other extraordinary events such as We Did It! Wednesdays and Sunday magic shows. The venue is famous for its beer buckets, but they also offer complimentary non-alcoholic beverages. Located conveniently in Boston's historic North End, consider combining your night out with some delicious nearby Italian cuisine. Photo credit to Fun4All at pixabay.com
Article By: Alex Dryjowicz
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 minutes
22:00 - 22:15
Modern Pastry
257 Hanover St, Boston, MA 02113, USA
While strolling through Boston's North End, it would be criminal to pass on cannolis. There are tons of Italian bakeries in the neighborhood, but locals know Modern Pastry is the best place to go. Family-owned for over 90 years, Modern Pastry has achieved cannoli perfection. With a thin, crispy shell and fresh, creamy ricotta filling, these are the cannolis dreams are made of. Often compared to Mike's Pastry, the other cannoli king, Modern stands out for its authenticity. However, if you seek crazy flavors and large portions, Mike's might be a better pick. Photo credit to lucas_holiday at pixabay.com
Article By: Alex Dryjowicz
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 minutes
Privacy: public
About 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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