Boston Two Day Itinerary: Boston Weekend Itinerary
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This list of attractions can build a wonderful one or two-day Boston Itinerary.
Chinatown
Boston’s Chinatown is a small but packed neighborhood with dim sum spots, bakeries, and bubble tea shops worth checking out. If you're building a Boston weekend itinerary, it's an easy food stop between the theater district and the Common.
For a taste of all things China, plan to spend a few hours in the city’s historic Chinatown. Start your journey at the paifang gate at Beach Street. The adjacent park is lovely during a fair-weather season with native Chinese plants and a fountain. As you wander the streets you’ll find amazing dumplings, dim sum options, boba tea, and various small gift shops.
Boston Tea Party Museum
This floating museum gives you a crash course in revolutionary chaos, complete with shouting guides and fake crates tossed overboard. It's one of the more fun indoor things to do in Boston, especially with teens.
If you’re like me, you have some sort of vague grade school memory about some revolutionary folks throwing tea into the Boston Harbor. If you want to refresh your 18th-century American history knowledge a visit to the Boston Tea Party Museum is a perfect way to spend a few hours.
Museum features include full-scale replicas of two sailing ships from the era. The museum employs character actors filling the roles of all of your favorite revolutionaries. You will even have the opportunity to throw tea into the harbor! They do a nice job of making history come alive, though some may find it all a little silly and more suited for families with children.
Old State House
The Old State House is where the Boston Massacre happened and where the Declaration was first read to locals. If you're following a 1 day Boston itinerary, it’s a quick but worthwhile history stop.
An important historical building in the history of the United States, the Old State House is operated by the National Park Service. A steep USD$15 per person entry fee will let you inside, along with the nearby Old Meeting House. If you’re a history-obsessed traveler you might be excited about the exhibits.
If you’re not that excited, save the $15 and view the building from the outside. The two most important historical events happened outside the building anyway. In 1770 this was the site of the Boston Massacre and in 1776 this was the spot where the Declaration of Independence was first read to the citizens of Boston.
Freedom Trail
The Freedom Trail is a red-brick path through downtown that connects most of the city’s historic landmarks. You can follow it on your own or join a tour to hit cheap things to do in Boston without much planning.
The 2.5-mile trail across Boston is a great way to immerse yourself in the history of Boston and its role in the country’s fight for Independence. Many of the historic sites on this list are part of the Freedom Trail.
If you search Google for the Freedom Trail website, you can purchase tickets for interactive and guided tours of the route.
Faneuli Hall
Faneuil Hall is a historic marketplace that’s now filled with overpriced souvenirs and quick lunch counters. It still shows up on every two day Boston itinerary because it’s right next to the Freedom Trail and Quincy Market.
Faneuli Hall is a 250-year-old nationally registered historic building. The hall’s visitor’s center is a good resource for more information about the building. While Bostonians still gather at the hall for important events and political protests, the main function of the building is for shopping and eating. The inside of the building is lined with food stands and small gift shops and kiosks.
Paul Revere Ride and Old North Church
You can visit the Old North Church and Revere’s house in the North End, both tied to his midnight ride. They’re easy stops if you’re doing Boston with teens or brushing up on your early U.S. history in one afternoon.
“One if by land, two if by sea” is Another phrase American schoolchildren have taken to memory. In the tower of the Old North Church, one lantern signaled a British invasion by land and two lanterns signaled an attack across the Charles River. The church was built in 1723.
From here, partially according to history, and partially according to the shaping of history from Paul Revere's Ride an 1860 poem by Henry Wadsworth Longfellow, Paul Revere began his infamous ride to alert “the British are coming!”
North End
The North End is Boston’s Italian neighborhood, famous for cannoli, pasta, and tight brick alleys. It’s a solid pick for dinner if your Boston 2 day itinerary ends anywhere near downtown.
Many of Boston’s most historic homes and buildings are in the North End. It is also home to the city’s Little Italy cultural neighborhood. There are several historic sites like Paul Revere’s House and Copps Hill Burying Ground, a historic cemetery.
You will also find some amazing shopping and dining in the area. It’s always a great idea to find an Italian bakery and pick whatever looks best to you at the moment from the display case. Cannoli anyone?
Boston Common and Public Garden
Boston Common is the oldest public park in the country, and right next to it is the Public Garden with its swan boats and weird statues. They’re easy wins on any Boston weekend itinerary and good spots to slow down between museums.
Boston Common is the oldest city park in the United States. In the summer it is a great place for a picnic, in the winter you will find a popular ice skating rink. There are many moderately interesting sites and statues around the park, but a nice stroll through the paved park paths should bring anyone joy.
Across the street, you will find Boston Public Garden a completely free botanical and arbor garden with beautiful flowers, trees, and ponds. In the summer you can rent a swan boat for the full experience.
Dunkin’
You’ll see Dunkin’ on every corner—locals don’t call it “Donuts” and they don’t go a day without it. If you're visiting from out of town, grabbing a coffee here is practically a cultural requirement in any 1 day Boston itinerary.
America runs on Dunkin’, but Boston is serious about it. The first Dunkin’ Donuts opened in nearby Quincy, MA in 1948. Since then the chain has become a staple on the East Coast of the United States. Something about sipping some Dunkin’ coffee while walking the streets of Boston feels right.
