We have good news and bad news. Bad news: Two days in Boston (probably) isn’t enough time to get you a thick, Boston accent. Good news: You can still have a complete Boston experience that will have you feeling like a local in no time. With authentic local food, historic landmarks, and iconic entertainment, this weekend itinerary in Boston is the ultimate Beantown guide.
Time to get your 48 hours in Boston off to the right start. Head over to Mike and Patty’s, just off the Freedom Trail and near Boston Common. Enjoy a classic American breakfast and a cup of coffee to fuel up for the day. We recommend the Robbie, with roasted turkey, cheese, and avocado on toasted multigrain. And of course, you’ll want to add bacon, because bacon. This has been on the menu since the restaurant was founded in 2008, and is still a favorite.
You will appreciate this time in Boston even more if you understand the history of the roads you’re walking. Every corner seems to offer a new connection to the past, and it can be easy to miss. Immerse yourself in the Freedom Trail with a self-guided audio tour or with a personal tour guide. Dive deeper into every detail, from the cobblestone streets to 19th-century architecture. Hear stories about famous landmarks like Beacon Hill, Faneuil Hall, King’s Chapel, and Trinity Church. Now be honest, how many of those do you remember from your 8th-grade history class?
After literally walking through history, it’s time to sit back and let a conDUCKtor show you around. If that pun quacked you up, just wait until you board the duck boat for your amphibious tour of the city. Enjoy a tour around town and familiarize yourself with the different neighborhoods and hotspots. Once you’ve had your fill of land, plunge into the Charles River and see Boston and Cambridge from this unique perspective.
Take the trolley to the North End and give yourself plenty of time to explore Boston’s oldest neighborhood. Browse the multitude of shops and grab a coffee at one of the local coffee shops. Pause to gaze up at the blend of modern and historic buildings, and keep an eye out for Paul Revere’s house. With so many restaurants to choose from, you might have a tough time selecting your lunch destination. For the full culinary experience, take a three-hour food tour of the neighborhood. For the avid pizza fans, there’s a tour specifically dedicated to the North End pizza scene.
Inspired by the history that surrounds you? Ready to feel the thrill of heaving a crate of tea into the ocean, just like the rebellious colonists? Head over to the Congress Street Bridge and reenact the famous Boston Tea Party. You won’t just be watching the events unfold, you are going to play a role. After you learn the details of your character, march with the crowd from the Meeting House to Griffin’s Wharf. Climb aboard the authentically restored tea ships and make your stand against taxation without representation. You can also explore the museum and learn from interactive exhibits, 3D holographic characters, and a wraparound theater.
Sometimes, you just want to go where everybody knows your name. Pull up a seat at Cheers! and enjoy a meal in the classic bar where the famous sitcom was filmed. Think you can take on the Norm Burger? See if you can eat the entire double burger with Muenster cheese, onion rings, lettuce, tomato, and mushrooms. If you succeed, you will have a spot on the Norm Burger Hall of Fame. If you don’t…that’s probably just as good
Wake up early for a stroll through Boston Common or a run in Boston Public Garden. Enjoy the serenity of Frog Pond amid 50 acres of garden in Boston Common. Across the street is Boston Public Garden, America’s first public garden and known for its iconic Swan Boats. Along your run, try to count the different trees you see. There are over 600 varieties, so it will certainly keep you distracted.
Grab a coffee and breakfast at Thinking Cup, just a few steps from Boston Common and a local favorite. With vegetarian, vegan, gluten-free, and dairy-free options, you are sure to find something that fits your preferences.
Remember those Swan Boats you saw on the pond in Boston Public Garden? Looked pretty nice, right? Treat yourself to a relaxing morning on the water. This has been a Beantown favorite since 1877, so you have just become a part of history (again). Boats are maintained by fourth-generation boat builders descended from Robert Paget, the original Swan Boatbuilder. They probably know what they’re doing at this point.
Make your way to Sam LaGrassa’s for a classic Boston deli lunch. You can’t go wrong with the Pastrami Diablo, Rumanian pastrami topped with Monterey jack cheese. Toss in Bermuda onion, chipotle mayonnaise, barbecue sauce, hot cherry peppers, and applewood smoked bacon on a French roll. You can thank us later when your mouth isn’t full.
The Green Monster beckons, and it’s time for you to head over to Fenway Park for a Boston Red Sox game. This is the oldest active ballpark in the United States and has seen six World Series victories for the Red Sox. Sit back and enjoy America’s Pastime at this iconic stadium, built in 1912. Sing along with 37,000 strangers, as you belt out Sweet Caroline before the bottom of the eighth inning in a Red Sox tradition. If you happen to be in town for a Red Sox-Yankees game, get ready for one of the most intense rivalries in sports.
Before you leave, make the time to visit Cambridge and walk the campus of Harvard University. Established in 1636 and one of the most prominent universities in the world, Harvard is steeped in tradition and educational excellence. To get a better understanding of campus life and hear stories from a current student, take the Hah-Vahd tour. Your tour starts in Harvard Square and explores well-known landmarks such as Johnston Gate and Widener Library. If you need some inspiration for yourself or a prospective student, this might be the key to filling out that application.
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