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Explore  / Boston, Massachusetts

Boston City Spotlight

Jackie Martucci
Contributor
Jackie Martucci
@eventsbyjackiem
Read a local's take on Boston ↓

Overview

Boston surprises newcomers with its unique blend of loyal, lovable residents and unmatched accessibility to diverse experiences. Far from being just another cold New England city, Boston offers the best of both worlds—vibrant city living with easy access to beaches and exceptional seafood.

The city's character is defined by its walkability and the genuine warmth of Bostonians, whose loyalty extends far beyond movie stereotypes. Boston's waterfront location brings breezy days year-round, but the climate is more moderate than expected, with only January and February bringing true chill. The city serves as a perfect hub for exploring New England while providing world-class urban amenities, from North End Italian dining to live games at Fenway and TD Garden.

Highlights

The Business Community

Q: Are there any local entrepreneurs, artists, or small businesses you think define Boston?

A: So many! Being in the events world, I get to work with a lot of amazing entrepreneurs from Boston. To view some wonderful local art and culture, visit any of the amazing museums or hit SoWa Market in the summer. For local food /produce, check out Boston Public Market. If history is more your thing, head over to the Cambridge Antique Market for some treasures!

Local insight

Q: What are some places in Boston that tourists often overlook, but locals swear by?

A: Enjoy the Boston Public Gardens or a stroll along the Charles. Enjoy some shawarma at Garlic 'N Lemons or Boston Shawarma. After a night out, enjoy some late night pizza at Joe's or Anchovies. Things that are, admittedly, a bit touristy but that local still love: enjoy a whale watch tour, hit one of many breweries (Trillium in the Seaport is a fave), enjoy a cannoli from Mike's Pastry (they are that good!), check out the Harvard Museum of Natural History!

Events in Boston

Q: It's a city known for sports, but what are some events we might not know about?

A: Boston is a terrific hub for so many types of events! It's easy to catch a great concert or even a comedy show. In late spring/early summer, Boston Calling Music Festival brings in some amazing headliners. Visiting Snowport in the Seaport is a 'must do' (even if it's a little touristy) in the winter months and a visit to the iconic Isabella Stewart Gardner Museum is a must!

New comers intel

Q: What would surprise newcomers the most about Boston?

The Great Molasses Flood. How loyal & lovable Bostonians are—it's not just an attitude made for actors to portray in movies! How unique it is—you can get the best of city living while also having a taste of beach living on your days off (with some of the BEST seafood always at your fingertips!!)

Q: Are there any neighborhoods in Boston that are underrated but offer an awesome community vibe?
Southie. Very community oriented but not always top of mind for people visiting. Somerville is pretty sweet too but likely more $$

Key points to know

Transportation Reality

Leaning on your own two feet and public transport is the way when in Boston! Keeping a car in the city can get very expensive, very quickly and you'll find that you hardly use it!

Weather Strategy

That really depends on the day but honestly, not that cold! January & February are pretty chilly (just like most of New England), but the rest of the year is usually comfortable. That said, it can get breezy in Boston on any day of the week, we are right on the water! Be smart and dress in layers...

Housing Market Challenges

Overall, I'd say it's relatively easy to find housing but that you have to be willing to stretch those dollars a bit if you have a desired neighborhood in mind. Southie, or areas just outside the city, such as Medford, are more affordable options.

City Layout Adaptation

Don't be intimidated by Boston's non-grid layout—it's part of the charm. The seemingly chaotic street pattern becomes logical once you understand the T system and embrace walking. Give yourself extra time and you'll discover the city's true walkable nature.

Local Loyalty

Bostonians' reputation for loyalty and warmth is genuine, not just Hollywood fiction. This creates a welcoming environment where community connections run deep and local businesses thrive with neighborhood support.

About the contributor

Jackie Martucci leads Events by Jackie M, a Western-Massachusetts planning studio that crafts weddings, fund-raisers, and destination celebrations across New England and beyond. Celebrated for her “Jackie-of-all-trades” versatility and guest-first mindset, she orchestrates seamless, personal experiences while volunteering with the Junior League of Greater Springfield—an approach that earned her a spot in BusinessWest’s 2022 “40 Under 40.”

Jackie Martucci
@eventsbyjackiem