Old meets new in South Boston, where long-time Irish Catholic families live among young professionals and a diversity of newcomers. Where the Seaport boasts tall, glassy new office towers and hip restaurants along the water, others in the south of Southie take up in converted factories and warehouses, recognizant of the neighborhood’s working class history.
An important note to visitors: South Boston is not the same as the South End. And if someone says ‘Southie,’ they’re referring to South Boston. When you visit, the difference is clear: whereas the South End is composed of Victorian brownstones and Gothic touches, South Boston is distinctly industrial – old brick and iron factories of the early 20th century house new businesses and apartments, while the Seaport is home to an Information Age construction boom of sleek glass towers and contemporary architecture.
At the neighborhood’s northernmost point, the Fort Point Channel, visitors to South Boston cross over a trio of bridges, each with its own distinct tourist hallmarks. Congress Street bridge offers access to the Boston Tea Party Museum, its replica ship settled in the channel. From the Seaport Boulevard crossing, which stretches from James Hook Lobster Co. and the renowned Barking Crab seafood restaurant, pedestrians can see the old Northern Avenue Bridge, built in 1908 and now defunct. On the Summer Street bridge, you can look up to the skyline to find a neon relic from the early 1900s that still lights up the district sky, boldly proclaiming BOSTON WHARF CO. INDUSTRIAL REAL ESTATE. Signs of those early industrial charters still mark the old brick facades that lead you past hotspots like the Children’s Museum and the giant Hood Ice Cream jug and food stand. If you look up and above the new storefronts and Dunkin’ Donuts doorways, you find peeling paint and greening copper medallions from old fisheries, traders and manufacturers. Meanwhile, new freight ships slowly roll past in the harbor, their massive crates ready to be unloaded nearby.
South of the Seaport, past the Convention Center and long standing Gillette factory, the construction boom begins to merge with the older clapboard row buildings that have housed Southie residents since the late 1800s. While the glass towers of the Seaport stretch towards the sky, blocks of residential apartments stand in uniform, three-story townhouses interrupted by the modern conveniences of supermarkets and new charter schools. To the east, the Telegraph Hill neighborhood stretches into the Harbor, the peninsula leading to Castle Island.
South Boston roots: Revolution, Irish Catholic immigration and marching into the new era
A mighty landmark, Fort Independence on Castle Island still stands as a quiet reminder of South Boston’s legacy in the Revolutionary War. Now connected to South Boston by land, the fort is the oldest continually fortified granite site in the former British North America. During the Revolutionary War, George Washington sent cannons into the adjacent Dorchester Heights, pushing the force of the Continental Army against the British siege of the city. The subsequent evacuation of the British forces is still celebrated by locals as Evacuation Day. On March 17 1776, orders were given that if soldiers wished to pass through the continental lines, the password was ‘St Patrick.’ Fittingly, the holiday celebrations are most strongly observed by South Boston’s most notable residents: descendants of Irish Catholic immigrants.
People of Irish descent make up the largest single ethnic group in Boston. Irish people came to Boston as early as the colonial era, as indentured servants, but the Great Famine of the 1800s saw a massive wave of Irish emigration, with most immigrants settling in Charlestown and Southie. Though at first unwelcome by the Protestant ‘Yankees,’ Irish volunteers in the Revolutionary and Civil Wars helped the Irish Catholic to assimilate better. In 1901, the first annual Saint Patrick’s Day Parade was launched, and is still a celebration of the retreat of British forces and the Irish-American heritage that remains so strong in the South Boston neighborhood. Notable figures on floats have included John F Kennedy and Jacqueline Bouvier Kennedy, as well as his brothers Robert and Ted. Irish nationalists marched unofficially in the parade in the ’60s and ’70s, and protested violence in Northern Ireland by draping the tricolor flag over a coffin they carried through the streets.
Immigrants comprised a huge portion of the labor force in South Boston, working in the foundries, factories and shipyards nestled along the harbor, and this in part contributed to the expansion of the city in the 1800s. Later, in the ’70s and ’80s, it was notorious as a battleground between rivaling Irish gangs, most notably the Winter Hill Gang led by James ‘Whitey’ Bulger. Bulger himself grew up in nearby public housing opposite Joe Moakley Park.
As industry and technology changed in the 20th century, many businesses in the neighborhood shuttered, and Southie saw little traffic compared to other parts of the city.
A wave of change and development
More recently, the South Boston neighborhood has seen an extreme increase in construction and investment, after former Mayor Thomas Menino announced a development plan in 2010. Those plans have since transformed the seaport into the ‘Innovation District,’ modeled after the 22@ urban renewal model that brought new economic and social development to neighborhoods in Barcelona.
Frank Zanti, general manager of the Yankee Lobster Co., has witnessed the change firsthand. He’s been managing the business, a family-run company founded in the 1950s, since 2010. The Zantis moved shop to South Boston in 1999, to the current storefront on Northern Avenue.
“There wasn’t much here before. There were little mom and pop shops, basically. [The family] wanted to get involved with the development, never really imagining what the Seaport would develop into,” Zanti says. “It’s been great to be here towards the ground level before any development was starting… It’s a melting pot now – tourists, businesspeople, more residents in the area. To try to appeal to all those demographics is challenging and also rewarding. There’s so much energy and passion down here.”
Stefanie, a resident of South Boston since moving from the Back Bay in 2010, says even with new developments, the close community vibe remains strong. “We have noticed that more and more young families are moving in, and we love that,” she says. “We love seeing other families walking, enjoying the playground and going out to eat just like us. We feel safe and so comfortable in South Boston; we definitely won’t be leaving any time soon.”
Where to explore in South Boston
Nowadays, an easy and leisurely way to navigate the northern half of South Boston is to follow the Harbor Walk from the Fort Point Channel. Head towards Dorchester Bay and you’ll pass the old factories, find crops of new restaurants and storefronts popping up, and find yourself at the Institute of Contemporary Art. The ICA was founded in 1936 as the companion foundation to NYC’s MoMA, but found its new, permanent home in the Seaport in 2006. The large building houses rotating exhibitions, shows art films in its large, comfy theater and puts on First Friday parties on its back porch area on the water.
Further along the Harbor Walk, you’ll find Harpoon Brewery’s main Boston factory and taproom. You can take a scheduled tour or sit down at one of the large picnic tables to sample limited and seasonal brews and snack on warm, handmade salted pretzels. Walking back towards the Convention Center, you’ll find events and pop-ups on The Lawn on D, a green space that opens every summer with art installations, giant light-up swings and a beer garden for visitors aged over 21.
If you head out down the peninsula to take a free tour of Castle Island’s Fort Independence, stop by Sullivan’s for a lobster roll, or grab snacks for a picnic on Carson Beach. Though Telegraph Hill and City Point are heavily residential, there are plenty of paved walks and bike lanes for runners, joggers and casual strollers.
For shopping, while larger labels like L.L. Bean and Sephora are opening in the Seaport, the home-run, family-owned businesses cluster around West Broadway Street. Covet, a luxury consignment shop, opened in 2013. The store is clean and elegant and hosts one-of-a-kind vintage finds as well as like-new pieces from Burberry and Free People.
Foodie favorites and culinary hotspots
There’s no shortage of dive bars, family-run diners and new and exciting eateries across South Boston. In the Seaport, harbor views give way to classic, laid-back seafood spots alongside elevated, modern sit-downs. Further south and closer to Dorchester, plenty of new bars and restaurants have opened along West Broadway, making it a hotspot for young professionals and date nights. From mix-ups of American fare at Worden Hall to tacos at Loco Taqueria (their coconut margarita is a must-have), it’s easy to find the perfect plate for every hungry diner.
Lines often curl around the building for dishes at Yankee Lobster Co., a testament to the Zanti family’s fare. Customers come eager for fresh, buttery lobster rolls and fries at the cozy sit-down eatery, and some leave with take-out fish fillets, clams or chowder to cook up at home.
With more people flocking to the neighborhood, manager Frank hopes to balance the rewards and excitement of the business’s success with its humble, homegrown origins.
“We’ve partnered up with the Red Sox to become the official lobster roll. We were on the Food Network – Diners, Drive-Ins and Dives,” Zanti says. “With so many new developments going up around us, we are a small fish in a big pond. They have great views, beautiful establishments, and all that is okay. We want to stay true to our roots and stay a neighborhood hole in the wall… we want to have that really local feel.”
Where to eat in South Boston
The family business started in 1925, when James Hook and his three sons, Edward, James and Alfred, began trucking their daily lobster catch from Maine and Canada down to the fish piers. James Hook and Co. is still a family business managed by four siblings of the third generation of the Hook Family. Their dine-in stand, a charming spot with picnic tables and views over the Fort Point Channel, offers generous lobster rolls with mayo or butter, jumbo lump crab cakes, and several flavors of delectable chowder. Their retail selection offers bulk lobster, shrimp and crab to take away and cook at home.
A South Boston institution, Sullivan’s Castle Island is a popular food stand situated at the edge of Castle Island Park. It was founded in 1951 by Dan Sullivan and stayed in the family; four generations later, it’s a Boston landmark in its own right. Favorites include its lobster roll, fried clams and french fries and fried dough with cinnamon sugar.
Creative flavors and decor make Moonshine 152 a must-visit. Chef and owner Asia Mei creates seasonal menus that focus on bright, sustainable plays on local East Coast cuisine and Asian Fusion street food. Inventive, flavor-filled plates have included Amei and Arae’s ‘Treat Yo’ Self Tempura’ with Narragansett beer-battered cauliflower and a Cajun grilled tilapia with fried pickled green tomatoes and a spicy uni-shrimp butter. Moonshine 152 offers a weekend brunch with $1.50 oysters on the half shell, dinner every day and a late-night menu until 1.30am.
Lincoln Tavern is a crowd-pleaser. It welcomes you with its rustic, nostalgic decor, and its wooden beams and original tin ceilings are a callback to old-time supper clubs. Families fill in the front booths and back room while others file to the grand, wide bar. There’s brunch on both weekdays and weekends, and a long dinner menu with American classics, both familiar and with a fresh twist. But one of their bigger claims to fame is the Lincoln Burger: a wood-grilled prime blend beef with bacon aioli, Cabot sharp cheddar and caramelized French onions on a brioche bun. Pair it with one of the local brews on tap or try one of their many inventive, quirky cocktails.
Pastoral in Fort Point is cozy, laid-back, and sure to please. Artisan pizza is its true calling – it’s best practice to bring a friend or two and trade slices of their indulgent topping combinations. (Choosing one is never easy, but the spinaci e carciofi is splendid, especially when prefaced with a burrata to split.) In addition to rotational beer, sour ale and draft cider selections, they offer imported Italian craft beers by the bottle. A bonus for some foodies is that gluten-free crusts are always available.
Bars and nightlife
Drink is a well-known establishment created by Barbara Lynch. It’s a well-to-do cocktail bar serving up elegant drinks in the Fort Point neighborhood. You can order a craft cocktail with artisanal ingredients in a Prohibition-style setting, or you can ask for your own preferred cocktail; give the bartender a few of your favorite flavors, and they’ll create one for you.
Tater Tot nachos with fiery salsa, anyone? There’s an entire food truck located inside Coppersmith, a converted warehouse located in South Boston. Enjoy the chic industrial environment as you chow down New American cuisine like the brined and smoked wings, french toast with blueberry compote and orange maple syrup and smoked brisket hash. On a summer day, eat outside on the patio or check out the roof deck.
Local shops and businesses in South Boston
Seaport Tattoo is committed to quality and service like no other. From the extremely friendly staff to a great portfolio of custom work, Seaport Tattoo makes you and your ink feel like their number-one priority. Consultations are always free and their artists also offer thoughtful cover-ups and touch-ups.
Off West Broadway, Neatly Nested has become a go-to for thoughtful gifts and decor. Founded by Danielle McClure in 2013, Neatly Nested was originally a custom-finished furniture store with home-design services. Now, peruse and you’ll also find locally sourced and thoughtfully curated Boston- and Southie-themed gifts. You can find glassware and barware, art prints, laser-carved coasters and other design delights.
American Provisions is a sandwich lover’s delight – a small neighborhood shop committed to creating community through real food. They offer the best of what New England has to offer: everything from hand-selected artisan cheeses and cured meats to natural wine and craft beer. Much of their stock comes from artisans who hand-craft their produce, most in small batches, many made specially for the store.
Volcanic Iceland Epic Trip
meet our Local Insider
HOW LONG HAVE YOU BEEN A GUIDE?
WHAT DO YOU LOVE ABOUT YOUR JOB?
It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.
WHAT DESTINATION IS ON YOUR TRAVEL BUCKET-LIST?
I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!
Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.
KEEN TO EXPLORE THE WORLD?
Connect with like-minded people on our premium trips curated by local insiders and with care for the world
Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.
Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.
Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.
Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.
We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.