Cheers! 10 Things to Do in Boston

Rich in history and culture, Boston is an ideal locale for a weekend getaway full of sightseeing and seafood.

We stayed with my brother and sister-in-law in nearby Cambridge – a 20-minute ride away from the city on the T, Boston’s subway system.

With “locals” as our guides, we explored the city and all its beauty. Here are 10 things we recommend doing if you’re planning a trip to Boston!

10 Things to Do in Boston

Follow the Freedom Trail. The 2.5-mile, brick-lined route leads you to 16 historically significant sites throughout the city. Along the route, you’ll find the Massachusetts State House, Old North Church, Faneuil Hall and more.
Taste the seafood. You can’t visit Boston and not try the seafood! We enjoyed lobster rolls from the Boston Chowda Company.
Visit the Granary Burial Ground. Many famous patriots and revolutionary heroes are buried here, including Paul Revere, Samuel Adams and John Hancock. This is one of the sites along the Freedom Trail.
Take the cannoli. You won’t regret it! We got ours from Mike’s Pastry, a tourist hotspot that even the locals love. Pro tip: Get there early or you’ll be stuck in a line that stretches out the door and down the street.
Visit Quincy Market. While the rest of the city seems fairly tame in terms of crowds, Quincy Market is where you’ll find the highest concentration of tourists. Despite this, it’s worth the visit for its shops, eateries and energy.
Go where everybody knows your name. An iconic Boston landmark, the Cheers restaurant is a must-see (and actually serves food). There are two locations: the original Cheers (pictured below) and the Replica Cheers (at Quincy Market).
Try North End pizza. Boston is not known for its pizza, but there’s one exception: pies in the North End, aka Boston’s Little Italy and the city’s oldest neighborhood. We went to Regina Pizzeria, a North End mainstay that’s been open since 1926. The pizza was some of the best we’ve ever had (and we lived in Chicago for several years!).
Tour The Paul Revere House. Just a short (5-minute) walk from Regina Pizzeria, The Paul Revere House – home of the legendary patriot – offers a unique glimpse into American history. This is one of the sites along the Freedom Trail.
Relax at the Public Garden and Boston Common. These two parks, adjacent to one another, offer a relaxing retreat in downtown Boston. The Common, created in 1634, was America’s first public park, while the Public Garden, created in 1837, was America’s first public botanical garden. Boston Common is one of the sites along the Freedom Trail.
Treat yo’self! Enjoy cocktails, Mexican food and complimentary cotton candy at Lolita Cocina and Tequila Bar along the Harborwalk on the Fort Point Channel. The dark, gothic vibe makes this restaurant unique and strangely intimate – creating the perfect setting for a couple’s night out.