Top 5 Things to Do in Boston (History, Food & Fun!)

Boston is a city where history and modern life mash together in the best possible way. You can walk down cobblestone streets that Paul Revere literally trotted along, then turn a corner and end up in a ramen shop so good you’ll swear off instant noodles forever. I’ve spent plenty of time wandering Boston—sometimes in the rain, sometimes fueled purely by cannoli—and after all that, I’ve narrowed down my five favorite things to do in Boston.

These are the ones I’d happily repeat on every trip, the ones that balance history, food, and a little bit of fun. Planning a full weekend? Pair this with my Weekend in Boston Itinerary.

1. Shopping on Newbury Street

Boston isn’t all powdered wigs and Revolutionary history—sometimes it’s retail therapy. Newbury Street is an eight-block stretch in Back Bay lined with historic brownstones, trendy boutiques, and restaurants. It’s the kind of place where you can shop at Chanel one minute and dig through a thrift store the next.

I love wandering this street even if I don’t plan to buy much. It’s a mix of people-watching, architecture, and a little splurge here or there. Pro tip: walk all the way to the end, because it drops you into Boston Common, the city’s oldest public park and one of the best people-watching spots in town.

If shopping makes you hungry, duck into Santouka Ramen for a steaming bowl of their famous shio ramen. Fair warning: the place is tiny, the line is always long, and you’ll probably wait outside—but the creamy broth is worth it.

2. Eat Your Way Through the North End

If Newbury Street is Boston’s fashion runway, the North End is its food court—except this one is all handmade pasta, brick-oven pizza, and cannoli. The neighborhood is basically Italian food Disneyland.

Here are my must-eats:

• Giacomo’s Ristorante – Cash-only, no reservations, and always a line. But the butternut squash ravioli is rich, sweet, and worth every minute of waiting.

• Limoncello – Their famous rosette lasagna comes layered like a pinwheel and oozing with sauce. The bread basket here? From Iggy’s Bread in Cambridge, one of the best bakeries around.

• Carmelina’s – Cozy and always booked up. If you can get in, order the meatballs (perfectly tender, swimming in sauce) or their pasta alla Norma with eggplant, ricotta, and tomato.

• Regina Pizzeria – The North End location is the original, with its century-old brick oven. Get a classic cheese for the full experience, or the loaded Giambotta if you’re starving. Jay Leno and Ben Affleck both claim this is their favorite pizza, and TripAdvisor once ranked it #1 in the U.S.

• Neptune Oyster – The hot buttered lobster roll is the dish you’ll dream about later. Pair it with their chowder if you’re serious. Pro tip: the line starts forming around 10:30 a.m., so get there early.

• Monica’s Mercado & Salumeria – This is not just a sandwich shop—it’s an institution. Order the Italian sub “with everything” and prepare to wait in line (there’s always one). They slice the meats ultra-thin to order, pile them on fresh baguette bread, drizzle with olive oil and balsamic glaze, and top it all with cheese sourced from Connecticut. It’s one of the best subs I’ve ever had, and worth building into your North End food crawl.

• Mike’s Pastry vs. Modern Pastry vs. Bova’s Bakery – The famous cannoli trifecta. Mike’s shells are made in-house and stuffed to order (I say go classic ricotta with chocolate chips). Modern sources their shells from Golden Cannoli, a local company that sells nationwide, and I love their Boston cream cupcake alongside a mini cannoli. Bova’s is open 24 hours and makes their delicate Florentine shells in-house. They’re pricier and labor-intensive, but some locals swear they’re the best in town.

If you only have time for one neighborhood in Boston, make it this one. Come hungry, wear stretchy pants, and prepare to be ruined for Olive Garden forever. Between bites, check out shops like Loft & Vine for unique home décor or and gifts or I AM Books for Italian cookbooks and kids books.

3. Take a Pedicab Tour

Boston’s compact size means you can cover a lot on foot—but if your feet need a break, a pedicab is the way to go. It’s quirky, eco-friendly, and way more personal than a tour bus.

Your driver can zip you through Beacon Hill’s cobblestone streets, past the gold-domed Massachusetts State House, or along the Charles River Esplanade. Some will even customize the ride based on your interests—history, architecture, food stops. It’s also a great way to get candid photos since you’re literally being chauffeured around in the open air.

I always recommend this to first-timers. It’s fun, a little goofy, and surprisingly informative. If you want a good driver rec, let me know—I have a favorite who makes it feel like a private tour.

4. Take a Duck Tour

Yes, it’s touristy. Yes, it’s kitschy. And yes—you should absolutely do it. Duck Tours use World War II–era amphibious vehicles that roll through Boston’s streets and then splash into the Charles River for a skyline view.

The 80-minute narrated tour covers a ton of ground—from Boston Common to Faneuil Hall—and the guides lean into humor, which keeps it fun even if you’re not a history buff. Kids love it, but honestly, so do adults. And if you’re lucky, your guide may even let you take the wheel once you’re floating in the river.

It’s part history lesson, part comedy show, part boat ride—and that mix makes it unforgettable.

5. Visit the Boston Public Library (and Have Tea)

The Boston Public Library isn’t just a place for bookworms—it’s one of the most beautiful buildings in the city. Think grand staircases, murals, and a courtyard that feels more European than New England.

The real hidden gem, though, is booking afternoon tea in the Courtyard Tea Room. It’s elegant without being stuffy, and the spread is perfect:

• Scones with clotted cream and jam

• Finger sandwiches (the cucumber is classic, but I loved the smoked salmon, too)

• Mini pastries for a sweet finish

And the tea itself? Order the Ras Chai Latte, a slightly malty blend with cardamom, cinnamon, and cloves. You can add a hint of pumpkin spice, vanilla, or cinnamon syrup. It was honestly the best tea I’ve ever had—I still think about it.

We made it an occasion, dressing up in tea dresses and big derby-style hats, which made it feel like a little event in itself. Afterward, stroll the library’s galleries and courtyard—it’s as photogenic as it is peaceful.

Final Thoughts

Boston has plenty to offer, but these five activities balance the city’s best traits: food, history, and character. You’ll shop Newbury Street, eat your way through the North End, ride a pedicab through Beacon Hill, splash into the Charles River on a Duck Tour, and sip chai lattes in a library courtyard straight out of a movie.

The best part? You can squeeze all five into a long weekend—or stretch them across a week and mix in side trips. Either way, Boston will leave you full, happy, and probably carrying a box of cannoli on the plane.

If the weather turns, keep my Rainy Day in Boston guide handy.