Ask A Local: Insider Tips & Hidden Gems for Boston

Boston is one of those cities that doesn’t try too hard to impress and that’s exactly why you’ll fall in love with it. It’s compact, easy to walk or bike around, and full of charm, character, and neighbourhoods that feel like mini-cities of their own. We asked Lynda, a marketing freelancer who collaborates with Sim Local and who is a Boston local to give us the inside scoop on how to explore Boston like a true local - from scenic strolls, things to do to where to find the best coffee, food and pizza in town.

"Boston isn’t packed with over-the-top tourist traps — and honestly, that’s part of its appeal. You can easily wander the city on foot or rent a bike and explore from end to end. If you’re not sure where to start, head to Boston Common — it’s the oldest public park in the US and a great central point to begin your adventure.

For a bit of fun and a splash of history, hop on a Duck Tour (yes, those quirky amphibious vehicles) and get a unique view of the city from both land and water.

One of my personal favourites is The View at the Prudential Center. It’s the only real ‘touristy’ attraction I’d insist on going at sunset for stunning panoramic views. And if you’re into history, walking the Freedom Trail is a must. It’s a brilliant way to soak up Boston’s revolutionary past while exploring some of the city's most iconic landmarks."

"Every Boston neighbourhood has its own distinct personality and exploring them is like travelling between different worlds. I'd recommend exploring the following areas in Boston.

• North End is our version of Little Italy, filled with old-school trattorias and pastry shops.
• Back Bay is modern, stylish, and full of designer boutiques and brownstone charm.
• Dorchester and Southie are known for their Irish roots, younger crowd, and buzzing food and bar scene.
• South End gives strong New York Upper East Side energy — posh but down-to-earth, with galleries and fantastic eateries."

"For that classic taste of New England, you’ve got to try the clam chowder and lobster rolls. Head to Quincy Market for some solid classics, or check out the Barking Crab for seafood with a side of waterfront views."

"Boston really delivers when it comes to waterside walks and city views. Here are some of my top spots:

• Charles Esplanade – perfect for biking or strolling along the river.
• Seaport Seawall – stunning ocean views and modern architecture.
• Wollaston Beach – technically outside the city, but worth the short trip for coastal vibes.
• UMass Boston Seawall – another quieter spot with sweeping harbour views."

"If you're chasing golden hour, these are the places locals love:

• The View at the Prudential Center – hands-down my favourite for sunset.
• Wollaston Beach and Castle Island – peaceful, scenic, and totally Instagram-worthy.
• Quincy Quarries and Hull – for something a bit different with dramatic backdrops."

St. Patrick’s Day in Boston is on another level, especially in Southie. The parade, the energy, the community vibes. It’s a local tradition that’s not to be missed if you’re in town in March. The Boston Marathon is also one of the top events in the calendar year for Boston and this happens annually in April."

"Boston’s small size makes it ideal for day-tripping. Rent a car and explore:

• Newport, Rhode Island – charming seaside town with a gorgeous cliff walk.
• Cape Cod – beautiful beaches, quaint villages, and classic coastal New England charm.
• Nantucket or Martha’s Vineyard – hop on a ferry from Hyannis.
• Vermont & Maine – especially dreamy in the fall or winter ski season.
• Salem, Rockland, Portland – each offers a unique vibe, from spooky history to artsy food scenes."

"While places like Newbury Street, Boston Common, and Beacon Hill are understandably popular, you can still find quieter corners to explore. Try Downtown, Quincy Market, the Wharf, or the Seaport — all offer that perfect mix of Boston charm, history, and atmosphere."

"The Charlie Card is your ticket for buses and the T (our subway), and now you can even tap in with Apple Pay. But fair warning, public transit can be a bit slow, so bring comfy shoes and be ready to walk! For longer distances or out-of-town adventures, the commuter rail is super handy."

• Best Pizza: Source, Cambridge
• Best Guinness: McGonagles, Dorchester
• Best Cocktail: La Padrona, Boston
• Best Nachos: The Bowery, Lower Mills
• Best Coffee: Thinking Cup, Back Bay
• Best Pastries: Koko, Southie & Long Wharf
• Best Vegetarian Spot: Life Alive, Boston