Boston Weekend Itinerary:
The Perfect 2-day Guide
Boston has a special place in my heart as it was my first getaway outside of Canada since I moved to Montreal. After realizing we had a 3-day long weekend in May for Patriots’ Day, I decided to plan a last-minute trip — and I’m so glad I did! In this Boston weekend itinerary, I’m sharing my recommendations for the best places to visit and things to do.
I have wonderful memories from this trip: a walkable city packed with history, my first baseball game at Fenway Park (the Red Sox won!), and beautiful spring weather that felt so good after months of snow and rain in Montreal. Boston is one of those cities that feels surprisingly easy to explore thanks to its compact size, rich history, and beautiful neighborhoods. Most of the city’s main attractions can be visited in two or three days, making it an ideal destination for a weekend getaway.
Table of Contents
Best Boston weekend itinerary in 2 days
Freedom Trail
The Freedom trail is a 2-3 hour walking route that connects 16 of Boston’s most iconic historic sites including churches, burying grounds, parks, or statues.
You can sign up for a guided tour or follow the trail on your own at your own pace (which I did). We didn’t follow the entire trail and took some time to wander through the North End area, Boston’s Italian neighborhood and stopped by Quincy Market.
Here’s a list of the Freedom Trail’s 16 historic sites:
- Boston Common, America’s oldest public park
- Massachusetts State House
- Park Street Church
- Granary Burying Ground
- King’s Chapel and Burying Ground, Boston’s first Anglican church
- Boston Latin School, where a statue of Benjamin Franklin stands
- Old Corner Bookstore, the city’s oldest commercial building
- Old South Meeting House, which held religious services as well as public meetings, debates, and protests against British rule in the years leading up to the American Revolution
- Old State House, Boston’s oldest public building built in 1713
- Boston Massacre Site
- Faneuil Hall
- Paul Revere House, the former home of the patriot whose midnight ride became one of the most famous stories of the American Revolution
- Old North Church, famous for the “One if by land, two if by sea” signal to warn patriots about the movements of British troops
- Copp’s Hill Burying Ground
- USS Constitution
- Bunker Hill Monument, commemorating one major battle of the American Revolution
North End, Boston’s Little Italy
If you’re exploring the Freedom Trail, the North End is the perfect place to stop for lunch. The area is full of fancy and traditional Italian restaurants and shops. We grabbed yummy and affordable pizza slices at Galleria Umberto and Pauli’s for Boston’s famous lobster roll. I recommend booking in advance for sit-in restaurants as North End is a popular place for both tourists and locals.
The North End is also famous for its cannoli, with 3 main shops that you’ll often see recommended: Mike Pastry, Modern Pastry Shop, and Bova’s Bakery. Even though we were full after lunch, the smell of bakeries almost convinced us to make room for dessert.
We ended the day with a stroll along Boston Harbor and watched the sun set over the waterfront.
Back Bay and Newbury Street
Back Bay is a neighborhood known for its Victorian style homes and tree-lined streets, which is perfect for a leisurely stroll and some shopping. Our airbnb was actually in this area and it made our stay very easy to go anywhere.
I love a nice library so we stopped at the Boston Public Library. We were surprised that it’s actually much more than just a library. The building itself is beautiful with a grand staircase, stunning ceiling, and a peaceful courtyard (our favorite part).
Fenway Park
We came during baseball season, so it was the perfect occasion to watch our first baseball game! This was actually the activity we were looking forward to the most (my boyfriend watched sooo many videos about the rules and players beforehand haha).
As the oldest active baseball stadium in the United States, Fenway Park is full of charm and authenticity. The passion locals have for the Red Sox and the sports culture in general is impossible to miss. The energy was great during the game, and I really felt I was part of something when every fan sang Sweet Caroline together. There’s also a large choice of food and a huge shop to buy a souvenir of this memorable night!
If you’re not interested in seeing a game, you also have the option to book a tour and walk around the stadium.
Harvard University and MIT
Harvard and MIT are located across the Charles River in Cambridge.
As we visited on the weekend, no tours were available, so we explored both campuses on our own and were pleasantly surprised that we could enter some of the buildings without a guide. Before heading back to downtown Boston, we stopped along the Charles River to enjoy one of the city’s best skyline views.
Beacon Hill
Beacon Hill is a charming and picturesque neighborhood full of cobblestone streets and brick houses. We had a peaceful walk around Acorn Street, Cedar Street, and Louisburg Square and stopped at a café.
Chinatown
Before heading out to the airport, we decided to have a quick stop at Chinatown. If we had more time, we would definitely have tried one of the promising dim sum restaurants or a Chinese bakery! That’s one more reason to come back to Boston someday.
