BEST BOSTON 2-DAY ITINERARY: FUN THINGS YOU MUST DO

A Boston 2-day itinerary will immerse you in the history of the founding of the United States. But it’s not all history. The great food, architecture and fun destinations you find in this city make for a fantastic Boston weekend getaway or any 2 days in Boston.

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Patriotic statue in Boston 2-day itinerary

To See Boston in 2 Days, Start with The Freedom Trail

If you want to do Boston in 2 days, and it’s your first time in Boston, I recommend you start with a visit to the Freedom Trail.

The Freedom Trail is a “must-do.” This is a 2.5 mile (4.4 km) in Boston that covers 16 historic sites of critical importance to the history of the early United States. The tour starts at Boston Commons and ends at the U.S.S. Constitution and Bunker Hill Memorial at Charleston.

What’s good about this tour is that it will give you a great introduction to Boston proper. You’ll also get an in-depth exploration of key historical events that took place in the city while you are standing in the spot where they occurred.

You’ve got several options to do the Freedom Trail. You can take a tour with Freedom Trail Tours and visit these sites with a knowledgeable tour guide. Or, you can obtain a Freedom Trail map at any one of the tourist kiosks throughout the city and follow the trail on your own.

The actual trail is a well-marked red brick walk that you follow throughout the city. It’s fun to go at your own pace, visit at leisure whatever museum strikes your fancy, and stop along the way for snacks, drinks, or photo opportunities.

If you’ve already been to Boston and want to explore the city in-depth on your Boston 2-day itinerary trip, skip the Freedom Trail. Instead, hit key Boston sights and absorb all the city has to offer.

One transportation option you may want to consider is the Hop-on-Hop-off trolley. I personally love these inner-city trolleys and buses. They save you time and take you to the most important attractions.

I also love walking the routes if I have more time and the attractions are close to each other.

Day 1 of Your 2-day Boston Itinerary

Copley Square

I like to start a Boston 2-day itinerary at Copley Square because it is centrally located. It is a beautiful plaza surrounded by interesting architecture and many of Boston’s best hotels. The square is in the Back Bay neighborhood known for shopping and good restaurants. Back Bay is served by the MBTA (Massachusetts Bay Transportation Authority) Green subway line which connects seamlessly to all parts of the city.

The buildings surrounding Copley Square are impressive architecturally, but my favorite is the Boston Public Library with its two massive statues guarding the entrance.

Boston Common

From Copley Square, head to Boston Common just two blocks east and work your way to the Beacon Street side on the north edge of the park. This is the oldest park in the United States. The park’s interesting statuary, old-fashion carousel, a little lake, and wide expanses of green make for a beautiful stroll.

As you wander Boston, you will find many sites claiming to be the oldest bar, park, restaurant, or building in the United States. That’s part of the charming history that permeates this town.

Beacon Hill

Exit Boston Common Beacon Street’s north side and dive into the United States’ oldest and most iconic neighborhoods, Beacon Hill. Walking through Beacon Hill is like stepping back in time.

Acorn Street in Boston 2-day itineraryYou’ll see narrow, cobblestone streets, gaslight street lamps, and picturesque gardens in what is one of Boston’s most expensive neighborhoods. Make sure to visit Acorn street for a great photo opportunity.

The Massachusetts State House

Make your way back to Beacon Street and follow it east until you come to the Massachusetts State House easily recognizable by its golden dome. This is the state’s seat of government.

Massachusettes State House in Boston 2-day itineraryBuilt in 1798, the art and architecture in this building will amaze you. The entrance is free. Make sure to take a free 30- to 45-minute tour available 10 am to 3:30 pm on weekdays or take your own walking tour through the well-marked displays.

Granary Burying Ground

From the State House head south on Park street and left on Tremont Street where you will find the Granary Burying Ground, an iconic and fascinating cemetery.

I love cemeteries. I love their quiet, peaceful beauty and the history, insight, and soul you glean from reading the tombstones. The Granary Burying Ground is one of the United States’ most significant cemeteries from a historical perspective.

The cemetery was founded in 1660! In fact, it is Boston’s third-oldest cemetery. That means that some of the original settlers in Boston could have been buried there.

The people that ARE buried here include three signers of the Declaration of Independence. Also present is Paul Revere who, with his trusty steed, rode through the nascent colony at night warning the settlers that the British were coming, thereby positively influencing the turn of the Revolutionary War.

The cemetery is also the site of the Franklin family mausoleum, although Benjamin Franklin is not buried here. He is in Philadelphia, a city he loved where he founded the University of Pennsylvania.

The area around the Granary Burial Ground is a good place to catch your breath and get a snack or a drink before you continue your 2-day Boston itinerary.

Irish Famine Memorial

Just one street away from the Granary Burial Ground you will find the Irish Famine Memorial on School Street.

Boston claims the most concentrated Irish population for a city in the U.S., 20.4%. Therefore, the Irish Famine Memorial and its history mean a lot there.

Irish Famine Memorial in Boston 2-day itinerary This display commemorates the 1845 Irish Famine that caused one million deaths in Ireland and one and a half million destitute Irish to come to the United States seeking refuge.

It is a touching, poignant memorial, a fitting tribute to one of the many immigrant communities that made the United States what it is today.

New England Holocaust Memorial

A pleasant walk north on Congress Street will bring you to Union Street and another moving tribute to an historical event of epic proportions, the New England Holocaust Memorial. This is a glass exhibit displaying poignant impressions from the Holocaust victims. We walked through it in the rain which somehow made the exhibit that much more touching.

Part of the Holocaust Memorial in BostonThis is a unique memorial and a must-see in Boston.

Union Oyster House

Across the street from the New England Holocaust Memorial is the Union Oyster House. It is one of the oldest restaurants in the United States and the oldest in continuous operation since it opened. It looks it, too, with low-beamed ceilings, narrow stairs, and dark corners.

Boston's historican Union Oyster House in Boston 2-day itineraryI like oysters, bars, history, and beer so this place suits me just fine. Sit at the circular wooden bar where Daniel Webster once sat eating oysters and downing whiskey. The oyster “shucker” (that’s a real word) shucks the oysters right in front of you and delivers a tasty treat so fresh you can taste the ocean. Wash it down with a local brew and soak it all in.

Have a lunch or dinner at the Union Oyster House, a great place to eat while you’re in Boston.

Day 2 of Your Boston 2-day Itinerary

Start day two in Boston with the last of the must-see Boston sights.

Right down the street from the Union Oyster House is Faneuil Hall Marketplace. You can’t miss it. It is a combination of separate markets: Quincy Market and Faneuil Hall, shops, restaurants, and historic sites.

You can easily spend several hours wandering the many markets especially if you have lunch here. They also have cute, little desserts and chocolate shops.

Front shot of Quincy Market buildingHistory buffs will appreciate that it was here, in 1764, that colonists first protested British taxation. It was here where the words “no taxation without representation” were first spoken and ignited the War of Independence. For this reason, this hall is called the Cradle of Liberty.

The top floor houses the Ancient and Honorable Artillery Company and history abound everywhere you look.

Want More Options for Your Boston Itinerary?

Boston by Night

Boston shines at night with lots of options. Some include:

  • Seeing a play in the Theater District
  • Partying in one of the many clubs
  • Wandering the waterfront area (also great at daytime)
  • Taking in a haunted Boston tour

Given a choice, I’ll always opt for a ghost or vampire tour at night in a new city.

(By the way, New Orleans is the best city in the U.S. for ghostly goings-on. Take it from me who checks out ghost tours in every city I visit.)

Boston’s Museums

You may want to reserve what time you have left for visiting one or more of Boston’s great museums. Two come to mind. First the Boston Museum of Fine Arts. And if art is your thing, this is a full-day event, so keep that in mind. The MFA is the fifth largest museum in the U.S. with almost half a million pieces of art. It is right up there with the Met in New York or any of the top European museums.

The second must-see Boston museum is the Isabella Stewart Gardner. The location and the works inside were donated by the socialite it was named for. She created a cloister and a mansion to house her collection. When she died in 1924, she left the museum “for the education and enjoyment of the public forever.”

Boston has many other magnificent museums but if you’ve only got 2 days in Boston, try to hit these.

Boston’s North End – Little Italy

Your last must-see in Boston is the North End, where you will find Little Italy. I expected Boston’s Little Italy to be a bit on the touristy side with your standard pasta and pizza dishes. What I found were excellent restaurants serving traditional Italian cuisine at reasonable prices.

Restaurant in Boston's Little Italy neighborhood a must for first timers.I had received a recommendation and tested it out to my absolute delight! Limoncello at 190 North Street in the heart of Boston’s Little Italy is a joy. It is a wonderful experience of delicious food, and attentive service in a beautiful environment at a fair price. Try it!

Limoncello at Boston's Little Italy is fantastic!It’s also fun to walk around Boston’s North End with its interesting churches, yummy pastry and gelato shops, and shaded streets.

Boston is a cool town easy to fall in love with. Go for a weekend or more using this Boston 2-day itinerary as a base. What are some of your favorite spots in Boston? We’d love to know.

>>Download a PDF of this itinerary here!<<

Boston 2-day itinerary - Beacon Hill Street

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Know before you go.  Get a ton of insider info and background history on this great American city with these guides and reference materials.

 

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