Boston Travel Guide for Tourists Who Want to Feel Like a Local
June 2022
Kelly Brennan
So you’re headed to Boston for Massachusetts food and fun…. Sounds good, but if you’ve never been, you might not know where to start. Obviously, you have to hit all of the tourist spots like Fenway Park, but this is a guide of how to do Boston in two days and feel like you’ve really experienced the city as a local.
First things first, you should be checking into the boutique Whitney Hotel located in the exclusive luxurious Beacon Hill neighborhood. Starting at $550 a night for a king size room, The Whitney offers views of the Charles River and away from the center of the city. If you’re looking for a cheaper option, there are AirBnB’s all over the outskirts of the city that you can stay at and then take the T (subway) into the city for your exploration.
Located only 13 minutes away from The Whitney, and within walking distance, you have to head over to the Boston Commons, the oldest city park in the United States featuring plenty of history and beautiful greenery to see. Adjacent to the Boston Commons is the Boston Public Garden, which spans more than 24 acres. This Victorian-era garden is home to the famous statue “Make Way for Ducklings.” The gardens have beautiful sights to see year-round, but particularly in the spring for the thousands of tulips, and in the fall for the extraordinary fall foliage.
Once you’re done walking around the parks and sight-seeing, make sure to stop for lunch at Boston Burger Company on Boylston Street. You absolutely have to try the 420 burger and churro milkshake. The 420 burger features mozzarella sticks, fried mac and cheese, onion rings, fries, bacon, golden barbeque sauce, and American cheese. You’ll definitely need something sweet to wash it down, so try the “Churro-ly We Can Taco Bout It” milkshake. This massive milkshake is made with caramel, chocolate syrup, cinnamon toast crunch, full size churros, and a frozen Choco taco on top.
When you’re all stuffed with your burgers and shakes, head back towards The Whitney to go shopping on Beacon Hill. This is some of the best shopping you can do in Boston featuring shops like the East Coast Ivy Boutique, Follain a beauty supply store, and Thieves Next Door, which specializes in home goods. You could spend hours walking the streets of Beacon Hill wandering in and out of stores.
The next day, go to the Back Bay of Boston to look at the iconic luxury brownstones covered in ivy. Although you might not be able to afford one, because they’re up to $11 million or more, they sure are nice to look at. When you’re done there, head on over to the Boston Museum of Fine Arts. This is the 20th largest museum in the world. It contains more than 8,000 paintings and 450,000 works of art. It even features some really cool neon light art.
At the end of your trip, you can’t miss going to the North End for world famous cannolis at Mike’s Pastry. These cannolis are so good that I drove four hours to Boston just for them and then turned around and went home. The classic cannoli is chocolate chip, but there are up to 20 different flavors of cannolis you can try. I’m a true chocolate lover for cannolis, so I can’t recommend the classic chocolate chip enough, but if you want to branch out while still staying traditional, try the chocolate covered cannoli, you won’t regret it.
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