The Ultimate Boston Two Day Itinerary

This is our Boston two-day itinerary! This quaint city is Massachusetts’ capital and is part of the greater New England region. We had fun exploring Boston’s many historic buildings and sites. The presence of prestigious universities like Harvard and MIT gives the city an intellectual reputation too. And of course, this coastal city is renowned for its fresh and affordable seafood. Other than seafood, Boston has lots of great eateries too. We have outlined our two-day Boston itinerary below, which should be helpful if you are planning a trip to this charming city.

Day 1 Map

Day 1: Morning

Cafe Luna
It was our first day in Boston and we were feeling pretty excited. From our hotel, we headed over to Café Luna for breakfast. This cozy cafe serves a variety of comfort food such as waffles, panini, sandwiches and salads. I had the “Kitchen Sink” Waffle and Egg Pasta ($13), which comprises a buttermilk waffle with bacon, scrambled eggs, and a small fruit cup. Raevian ordered a small Breakfast Sandwich ($6), a simple but tasty croissant sandwich with egg, ham, sausages and cheese. Since Massachusetts Institute of Technology (MIT) was just nearby, we made a quick stop at the campus before heading on to Harvard University. We would have liked to walk around MIT longer but our itinerary was already pretty packed.

Café Luna
Address: 612 Main St, Cambridge, MA 02139, USA
Phone: +1 617 576 3400
Opening Hours: | Mon: 7am – 5pm | Tue to Fri: 7am – 6pm | Sat & Sun: 9am – 5pm |

Harvard University

It is every nerdy Asian kid’s dream to study at Harvard University, and I happen to be one of them. It felt surreal to walk around this serene campus. Well, I guess even though I didn’t manage to secure a place at this prestigious college, at least I was lucky enough to tour the school campus.

After walking around the campus for about one hour, we went on to Harvard Square to get lunch. We grabbed a slice of pizza at the famous pizza joint OTTO Pizza, and had a sumptuous gourmet burger at Mr Bartley’s.

Day 1: Afternoon

Berklee College of Music
Since I once had dreams of becoming a guitar-wielding rockstar, I knew I had to check out the famous Berklee College of Music. Famous ex-students from here include John Mayer, Charlie Puth, Steve Vai, John Petrucci, Wang Leehom, and more! As I explored the building campus, I imagined myself to be a young Lee Hom going for his next music class.

Newbury Street
Newbury Street

Newbury Street is a mile-long street lined with beautiful 19th-century brownstone buildings. There is a wide variety of shops and restaurants here, making it an awesome place to shop and eat. Over here, we saw the majestic Church of the Covenant, a historic Gothic Revival architecture built in 1867. You can check out the Newbury website for more details.

After Raevian was satisfied with her shopping, we went to Georgetown Cupcake to rest our legs and indulge in the delicious cupcakes. We ordered the Red Velvet ($3.25) and sat at the window countertop to savour it.

Georgetown Cupcake
Address: 83 Newbury St, Boston, MA 02116, USA
Phone: +1 617 927 2250
Opening Hours: | Mon to Sat: 10am – 9pm | Sun: 10am – 8pm |

Boston Public Library
Next, we made a quick stop at the Boston Public Library, which is the second-largest public library in USA (losing out only to the Library of Congress). We visited the charming Bates Hall, an iconic library hall with its green lamps, majestic barrel-arched ceiling, brown oak bookcases, and busts of famous figures.

Boston Public Library
Opening Hours:| Mon to Thur: 9am – 9pm | Fri & Sat: 9am – 5pm | Sun: 1pm – 5pm |
Website: www.bpl.org

Day 1: Evening

Copley Square

Copley Square is a public square with a beautiful green lawn. It is right next to the Trinity Church. We were impressed by the beautiful facade of this Romanesque architecture built in 1877.

For the ladies, Copley Place is a five-minute walk away. This high-end shopping mall offers luxury brands like Christian Louboutin, Tiffany’s, Jimmy Choo, Ferragamo, Saint Laurent, Hugo Boss, Louis Vuitton, etc. It is connected to three luxurious hotels: Westin, Marriott, and Sheraton.

Copley Place
Address: 100 Huntington Ave, Boston, MA 02116, USA
Website: www.simon.com/mall/copley-place

Atlantic Fish Company
After a day of touring and shopping, it was finally time for dinner. We went to Atlantic Fish Company for dinner. This casual seafood restaurant is known for its delicious seafood dishes and is very popular among the Boston locals. My Linguine with Clam Sauce ($23) was on point, with the clams cooked perfectly and noodles al dente. Raevian had the Fish and Chips ($22). The fried Atlantic snapper haddock in lager batter was really fresh and had a nice smooth texture. After the satisfying dinner, we went back to our hotel and crashed in our beds.

Atlantic Fish Company
Address: 761 Boylston St, Boston, MA 02116, USA
Phone: +1 617 267 4000
Opening Hours: | Mon to Thur: 11.30am – 11pm | Fri and Sat: 11.30am – 11.30pm | Sun: 11am – 11pm |

Day 2 Map

Day 2: Morning

Thinking CupThe next morning, we went to the famous coffeehouse Thinking Cup for breakfast. This cozy cafe is famous for its gourmet coffee and delicious sandwiches. We perked ourselves up with a steaming cup of Cappuccino ($3.50). The coffee was full-bodied with a smooth and creamy texture. We ate some delicious sandwiches before heading out to explore the Boston public parks.

Boston Common and Public Garden
Boston Common and Public Garden are two beautiful public parks in Boston that are adjacent to each other.

First, we went to Boston Common (also known as “the Common”). This public park was built in 1634 and is one of the oldest parks in USA. We enjoyed exploring the serene park and revelling in the the tranquil greenery. We came across the “Soldiers and Sailors Monument”, built to commemorate the Massachusetts soldiers and sailors who died in the American Civil War. We also saw many people skating in the “Frog Pond”, an ice skating rink in the park.

After that, we went to the adjacent Boston Public Garden (also known as the “Public Garden”). It was completed in 1837 and is a more manicured park. This park is beautiful too. We saw the imposing “Equestrian Statue of George Washington”, a charming 12-metre statue that was completed in 1869.

Day 2: Afternoon

Beacon Hill
Acorn Street

Massachusetts State House

From the gardens, we walked to Beacon Hill. This historic neighbourhood is known for its Federal-style houses, gaslit streets and brick sidewalks. One of the most famous spots here is Acorn Street, a quaint and pretty street paved with cobblestones.

We also saw the Massachusetts State House, a Government building located in Beacon Hill. It houses the Massachusetts General Court and the offices of the Governor of Massachusetts. Completed in 1798, this National Historic Landmark is considered a masterpiece of Federal architecture.

Faneuil Hall Marketplace
By now, we were pretty famished. Therefore, we took a Lyft ride to the bustling Faneuil Hall Marketplace. This festival marketplace has over 100 restaurants and retail shops. It consists of four buildings, each with different restaurants and shops: Fanueil Hall, North Market, South Market, Quincy Market.

We loved the food hall in Quincy Market, where we indulged in the famous chowder from Boston Chowda and scrumptious pizza from Pizzeria Regina. This food hall is definitely a great place for foodies.

New England Holocaust Memorial
From the marketplace, we walked for a few minutes to the New England Holocaust Memorial, a memorial built in memory of Jews who were killed during the Holocaust. Built in 1995, it consists of six glass towers, each symbolising a different major extermination camp. It can also be taken to mean the six million Jews killed, or the six years that the genocide took place (1939 to 1945). Looking at the memorial, it was a disquieting experience to be reminded of the horrors of the Holocaust.

Day 2: Evening

North End
Statue of Paul Revere

After that, we went to the North End. This is the oldest neighbourhood in Boston and has plenty of restaurants, shops, and tourist attractions. The district is known for its Italian American population and Italian restaurants.

Our first stop in North End was the pretty Christopher Columbus Waterfront Park. This family-friendly park has green lawns, trees, great waterfront views and a beautiful wisteria walkway. There is also a playground for kids to run about and burn off their energy.

Next, we went to the Old North Church (officially the “Christ Church in the City of Boston”), which was built in 1723 and is the oldest church in Boston. Near the church is the Statue of Paul Revere, built in 1940. This beautiful equestrian statue commemorates patriot Paul Revere’s famous midnight ride to alert the American colonial soldiers of approaching British forces in 1775.

Our final stop in North End was the Copp’s Hill Burying Ground. This historic cemetery was built over 350 years ago! There are many interesting plaques here that provide a history of events in Boston.

The Daily Catch
Finally, for dinner we went to The Daily Catch. This homely Italian bistro is renowned for its delicious “Sicilian-Style” seafood and pasta dishes. For appetizer, we had the Calamari Scampi ($12.75), which consists of fresh squids sauteed with garlic oil, butter, lemon and wine, served in scampi sauce. However, the highlight of our meal was the Black Pasta Aglio Olio ($24), which consists of grounded squid sauteed with garlic and olive oil, served with squid ink pasta. This is hands-down our favourite restaurant in Boston! You can check out our full review of The Daily Catch.

The Daily Catch (North End)
Address: 323 Hanover St, Boston, MA 02113, USA
Phone: +1 617 523 8567
Opening Hours: | Daily 11am to 10pm |

Mike’s Pastry
After dinner, we went across the street to grab some delicious cannoli from Mike’s Pastry (yes we are gluttons). This famous Italian bakery shop is famous for its huge variety of delicious cannoli. We ordered Oreo ($4.50) and Chocolate Chip ($4.50). We ate the huge cannoli back in our hotel room. The ricotta filling tasted great, with a luscious texture and sweet flavour that tasted wonderful. We fell asleep with tired legs and satisfied tummies. The next day, we woke up super early to catch our flight to Quebec City. And that’s the end of our Boston two-day itinerary!

Mike’s Pastry
Address: 300 Hanover St, Boston, MA 02113, USA
Phone: +1 617 742 3050
Opening Hours: | Sun to Thur: 8am – 10.30pm | Fri and Sat: 8am – 11.30pm |

This article is part of our completely free and fantastic Ultimate Boston Travel Guide for First Timers. Why spend days researching when all your holiday information is simply a click away?

Itinerary Summary

Time	Day 1	Day 2
Morning	Cafe Luna	Thinking Cup
Morning	Harvard	Boston Public Garden
Afternoon	Berklee	Beacon Hill
Afternoon	Newbury Street	Faneuil Hall Marketplace
Afternoon	Boston Public Library	Holocaust Memorial
Evening	Copley Square	North End
Evening	Atlantic Fish Co	The Daily Catch / Mike’s Pastry