It started as local field trips in high school to check out the historic landmarks. Later, my trips to Boston included teen brothers, friends, relatives and more while they navigated this beautiful urban landscape by the ocean. It can be amazing to see Boston with teens, as they see real history come alive, or get a taste for what their future might bring as a college student.

Just a Little Lesson

Your teens may groan, but get your history lesson in early so you move on to the fun stuff. The Freedom Trail is a tried and true way to see a few hot-spots in a short amount of time. Walk along the marked red brick pathway that winds two and a half miles through Boston at your leisure. Some of the best places to pause at are Paul Revere’s Home, the old State House and the spooky Copp’s Hill Burying Ground.

Hanging in the ‘hood

Sometimes it’s easiest to just let teens wander with you though a new city. Boston is one of the most walkable destinations, with plenty of stores, coffee shops, artwork and parks to simply explore. Some neighborhoods and areas are better than others though. While teens might find the financial district and stuffy South End a little boring, they might feel more at home elsewhere. First, make the trek out to Fenway if your crew is into Boston sports. Tons of college aged students and young people hang out the Kenmore area where Fenway Park is located too, in sports bars, outdoor parks and more.

Other college areas include strolling through Cambridge to check out Harvard University campus, or even West Boston by the Massachusetts Institute of Technology, also known as MIT. Artsy teenagers will not have to wander outside of downtown to encounter others their age oozing with talent, as Emerson College owns a few venues in the Theater District. Your whole family can see a discounted performance put on by students, from comedy acts and lectures to musicals and concerts.

Teen Approved Dining

It seems as if Boston was made to cater to teen tastes. To feed your older, pickier eaters, doesn’t necessarily mean you only have to do chain restaurants and boring fast food joints. If they can handle fish and chips, make sure you try a place in the Seaport like the Legal Seafoods or James Hook & Co. Both have fun views of the harbor. Burgers can be found at Gather along with a cool hipster vibe indoors and out. Most teens will dig into a pile of spaghetti and meatballs too, so swing by the North End for some of the best Italian food in the city. Have your teen sip their first espresso too at Cafe Vittoria – while the adults have a spiked one with amaretto or cream liqueur. Finish the evening at a stop by Modern Pastry. You might see everyone else make a beeline for Mike’s, but we swear Modern has just as good cannoli and treats with half the wait time.

This post was in collaboration with Best Boston. All opinions are of the author.