NortheastTop City Vacations

The Neighborhood Guide: Boston's Southie

By , March 11th, 2016

South Boston used to be rough. In the seventies and eighties, infamous mobster James ‘Whitey’ Bulger ran the streets with his gang of goonies ready to take people out if they crossed him. He ran the criminal underworld, surviving off extortion and loansharking among other things. Boston’s ‘Southie’ neighborhood, as the locals call it, was a tough place where kids grew up brawling on the streets and blue collar workers (including many Irish immigrants or of Irish ancestry) flooded Catholic churches on Sunday morning and hit the local watering holes by night.

A lot has changed since then — in the past 10-15 years total gentrification has taken over the once unsafe South Boston neighborhood. Young professionals realized that prime real estate at low prices was a reality in Southie and young families were eager to take advantage of the neighborhood’s proximity to multiple beaches.

Boston’s Southie



Photo by Craig Cloutier CC BY

Now residents in Southie are seeing posh new cafes and vegan restaurant pop up daily, replacing seedy long-time local hangouts. Gourmet markets, vintage shops and hipster beards have moved in — making South Boston an eclectic mix of old rough and new chic — enter SoBo. No need to worry about safety in Southie anymore (no more than any other city), since you now can safely sip your hazelnut, lavender soy cappuccino as you partake in some prime hipster-watching.

Famous movies filmed in South Boston: The Departed, Gone Baby Gone, The Town, Good Will Hunting, and Boondock Saints. 

trivago Hotel Pick | ALOFT BOSTON SEAPORT


Photo courtesy of the Aloft Boston Seaport hotel.

Typically, people tend to separate the Seaport area from the real ‘Southie’ neighborhood in Boston, however, technically Seaport is part of South Boston, making it the ‘rich’ side of Southie.

The vibrant color, modern architecture and funky vibe of the Aloft hotel will make you feel like you’ve stumbled into a tech startup office. Each guestroom is decked out in bright hues and bold shapes creating a modern retro ambiance. You’ll also be able to get some creative juices flowing or just make a very detailed plan for the day at the ergonomic work station (available in every room). In the evening, head down to the hotel bar WXYZ for signature cocktails and music.

The hotel is in the perfect location to give you a glimpse of the Seaport shops, from where you can take an ocean-side stroll along the Boston Harborwalk until you reach the heart of old Southie.

View Hotel on trivago!

The Morning Coffee

My Diner



Not a fancy joint, but definitely the place to be for breakfast in Southie. Photo courtesy of the My Diner Facebook page.

Although most visitors are enjoying the refreshed face-lift of South Boston, longtime locals still have a few places they can still recognize from the good old days. My Diner is one of those places. A dive filled with old school character and a rough facade, My Diner transports you back to a time when Southie was still the rough side of the tracks in Boston and you had to watch your back. Chow down on a hearty breakfast of meatloaf and eggs with a strong black coffee to wash it down. Order Green Eggs N’ Ham (Pesto, ham bits, scrambled eggs and melted cheese) with bottomless coffee.

  • Address: 98 A Street
  • Hours: Mon-Fri 5 a.m.-2 p.m. and Sat-Sun 6 a.m.-2 p.m.
  • Price: $2.95-$9.50

Doughboy Donuts & Deli



Don’t miss out on a maple bacon donut. Photo courtesy of the Doughboy Donuts and Deli Facebook page.

This is another old time favorite for homegrown Southies. The inside is definitely nothing fancy, but the donuts and danishes have a homecooked taste and the iced coffee is all the rave. Plus, who doesn’t love a donut joint that’s open 24 hours? Grab some lemon glazed donuts to go and enjoy them by the beach. Order the famous Boston Creme Donut and an Iced Banana Foster’s coffee.

  • Address: 220 Dorchester Ave.
  • Hours: 24/7
  • Price: Under $10

Sidewalk Cafe



Bite into a fluffy, warm bagel at the Sidewalk Cafe in Southie. Photo courtesy of the Sidewalk Cafe Facebook Page.

A bit of a walk from the Aloft hotel, but completely worth it, is the unassuming Sidewalk Cafe. A small shop with a mighty breakfast and strong coffee served up any way you like it. This is a local favorite for the newer Southie generation. Order the epic Breakfast Bomb (3 eggs, bacon, ham, and sausage topped with cheese and served on a French roll) and a Banana Hazelnut coffee.

  • Address: 764 E 4th St.
  • Hours: Mon-Sun 6 a.m.-10 p.m.
  • Price: $3.75-$12.99

What To See & Do

Things to do in South Boston are limitless — but here are a few activities that will show you the best side Southie has to offer and gives you a taste of both old and new Southie.

Boston Harborwalk



Explore the Boston Harbor via Harborwalk and explore miles of coastline that runs along the city. Photo courtesy of The Boston Harbor Association Facebook page.

The city of Boston has been working tirelessly in cooperation with the Boston Redevelopment Authority, the Boston Harbor Association and other third parties to tackle the Harborwalk project. The effort to clean, expand and make 47 walkable miles is currently sitting at 39 miles long and covers most of the seafront from North of Charlestown all the way down to the Northern end of Dorchester Bay.

For a long walk — start at the hotel and head south on D Street until you hit Broadway, take a left and head east towards the beach. Once you hit the water’s edge, take a moment to sit on a nearby bench or poke your toes in the sand as you look out over Pleasure Bay. From here, start north along the beach and follow the Harborwalk all the way up to the Freedom Trail.


The Freedom Trail



Follow history down the Freedom Trail in Boston. Photo courtesy of the Freedom Trail Foundation Facebook page.

Although not located in South Boston, the Freedom Trail is a must-see that you can work your way up to by strolling up the Harborwalk from the hotel. The Freedom Trail has 16 historical sights that are significant to the development of the American Revolution and Boston’s role in the liberation. Start from the southern end of the trail at the Boston Common Visitor’s Center.

  • Start Address: 147 Tremont Street
  • Trail Duration: 2.5 Miles 
  • Sights: 16 total including: Old Corner Bookstore, Bunker Hill Monument, USS Constitution and many more.
  • Price: Buy online for the discounted ticket price — $12.00 Adult Discount Ticket, $10.00 Senior/Student Discount Ticket, $6.50 Child (Ages 6-12)


The Institute of Contemporary Art



Hit the ICA for a mind blowing afternoon. Photo courtesy of The ICA Facebook page.

Easily accessible from the Boston Harborwalk is the Institute of Contemporary Art. Filled with extraordinary talent and creativity, the exhibits vary from inspiring to shocking. Take a contemporary look at the artistic revolution of  West Germany in 1974. The archival exhibition recreates Art into Society – Society into Art: Seven German Artists (29 October – 24 November 1974).  The exhibition is available from Jan 19th to March 13th. Film buffs can enjoy an array of choices at the ICA — catch a rare glimpse into the punk scene in Myanmar which blossomed under a military dictatorship in Punx Not Dead:Yangon Calling.

  • Address: 100 Northern Avenue
  • Hours: Tuesday-Sunday, 10 a.m.-5 p.m.
  • Price: General Admission – $15, Seniors – $13, Students – $10, Youth under 17 – FREE

Movie tour through South Boston


South Boston Boston Common
Photos by Matthew in Boston and Vignesh Ananth CC BY

The locals WILL laugh at you for paying money to see the once ‘rough’ areas of their neighborhood. Some of them might wonder why you want to spend time seeing where they used to brawl as youngsters or the corner that used to be famous for muggings — but with the gentrification of Southie and its new safe, squeaky clean image — there is a certain nostalgia for seedy underbelly of times past. Look no further, the Boston TV & Movie Suites Tour which takes tour participants to the dark corners of South Boston made famous by films like The Town, Mystic River and The Heat. For all the die hard Scorsese fans, you’ll get to see ten locations from The Departed, including the building from the heart-stopping rooftop scene.

  • Address: Exact location determined upon ticket purchase, general location can be found at Boston Common. 
  • Hours: May 22 – Oct 31 DAILY at 11 a.m. and  2 p.m. 
  • Price: $41


After a lot of walking through South Boston, you are definitely going to want to stop for some grub — luckily Southie is home to numerous mom and pop shops with delicious homemade menu options on top of the contemporary fusion restaurants for foodies popping up at every corner.




Try one of the famous hot dogs from Sullivan’s in South Boston. Photo courtesy of the Sullivan’s Facebook Page.

Sullivan’s started out as a humble concession stand on Castle Island in the 1950s with hot dogs selling for 15 cents each. Fast forward to today, and that concession stand is an impressive brick edifice still serving up some of the best hotdogs in South Boston (still at the startling low price of $1.90). Try the chili cheese dog with a fresh maple-flavored ice cream for dessert. Enjoy a stroll around Castle Island, where the famous Fort Independence still stands and the once isolated island is now connected to the the mainland by multiple causeways.

  • Address: 2080 William J Day Blvd
  • Hours: Mon-Sun 8:30- a.m.- 4 p.m.
  • Price: A famous hot dog goes for $1.90

American Provisions


American Provisions-South-Boston

Try the ‘Frenchie’ at American Provisions in South Boston. Photo courtesy of the American Provisions Facebook Page.

Explore the farm-to-table movement in South Boston by heading to American Provisions, a gourmet market that prides itself on locally-sourced, fresh produce. Grab some fruit, artisan cheeses and a bottle of wine and head down to the beach for a picnic lunch! South Boston is lined with beautifully coastlines and sandy beaches where you can relax and take in the sights while chomping down on smoked toma from a nearby family-run farm.

  • Address: 613 East Broadway
  • Hours: Monday – Friday 9 a.m.-8 p.m., Saturday – Sunday 9 a.m.-6 p.m.
  • Price: Gourmet sandwiches range from $5.95 to $9.95


Loco Taqueria & Oyster Bar


LocoTaqueria and oysters bar in South Boston

Photo courtesy of the Loco Taqueria & Oyster Bar Facebook page.

There is absolutely nothing that compares to crisp tacos with homemade guacamole, a plate of iced, crisp oysters and a cold beer. You must try South Boston’s local taco shop, the Loco Taqueria & Oyster Bar, which serves up some of the freshest ingredients on the East Coast. It also has a knack for incorporating mouthwatering seafood into most of its signature dishes.

  • Address: 412 West Broadway
  • Hours: Lunch/Brunch is only Sat-Sun 10 a.m. – 1 a.m. (Open Mon-Fri from 5 p.m. for dinner and drinks)
  • Price: $8-$18


Foodies know Southie is the upcoming spot for creative, New American dishes that will impress you. Not to mention some old local favorites that will give you the homey feeling that South Boston boasts so well.

Moonshine 152



Try the oysters at Moonshine 152. Photo courtesy of the Moonshine 152 Facebook Page.

If you’re looking to appease a sophisticated palette, Moonshine 152 is the place for you. This place is the real deal, fresh oysters, kale and pomegranate salad, and jalapeño crab are just a few of the scrumptious treats that await you. We suggest heading here for lunch, however if you’re hiding out in the hotel and still craving something fancy, you can order caviar delivery from this place!

  • Address: 152 Dorchester Ave.
  • Hours: Mon-Sun 5:30 p.m. – 10 p.m. (Late night menu available after 10 p.m.)
  • Price: $8.00-$29.00/dish

Local 149



Yum. Try Local 149 in South Boston for local produce. Photo courtesy of the Local 149 Facebook Page.

Local 149 lives up to its name by offering local produce and a friendly environment that will make you feel like a new friend in the area. You can enjoy creative cocktails at the bar or cozy up by the fire for an intimate talk over dinner with friends.  The menu is a mix of New American and home-style cookin’. Try the Pumpkin Risotto for a decadent dish, or opt for the hearty Fried Chicken and Waffles for a more comforting meal.

  • Address: 149 P Street
  • Hours: Mon – Thurs 4 p.m. – 1 a.m., Fri – Sun 11 a.m. – 1 a.m.
  • Price: $9-$22

Lincoln Tavern



Grab a beautiful bite at Lincoln Tavern. Photo courtesy of the Lincoln Tavern Facebook page.

Reminiscent of old school dining halls and supper clubs, Lincoln Tavern manages to evoke nostalgia while providing a hip vibe and a modernized menu. Try the hush puppies followed by the buttermilk fried chicken or the pumpkin ravioli.

  • Address: 425 W Broadway
  • Hours: Mon-Fri 11:30 a.m. – 2 a.m., Sat-Sun 10 a.m.-2 a.m.
  • Price: $8-$25


From dive bars and old watering holes to hip cocktail bars, South Boston’s safer image comes with a whole new wave of nightlife venues.

L Street Tavern



Get cozy at the Good Will Hunting bar, at L Street Tavern. Photo courtesy of the L Street Tavern Facebook page.

This is not part of new Southie, it’s actually an oldie that was used for the filming of the bar scenes in Good Will Hunting. The good news is there aren’t usually very many tourists in this place despite it’s Hollywood debut. The better news is that you can sit in the ‘Good Will Hunting Booth’ , daydreaming about Matt Damon sitting in that very booth in which you currently find yourself. Don’t be disappointed if you don’t recoginze the bar from the movie, a lot of renovating has occurred since the filming. Grab an Irish Whiskey or a Guinness to honor the bar’s Irish heritage!

  • Address: 195 L Street
  • Hours: Mon-Sun 12  p.m.- 1 a.m.
  • Price: Decent prices, cheap beers

Lucky’s Lounge



Get your dance pants on to enjoy the speak easy of Southie at Lucky’s Lounge. Photo courtesy of the Lucky’s Lounge Facebook Page.

If you’re looking for a no fuss kind of place, Lucky’s Lounge is half speakeasy half dive bar — and it’s fun. Come for late night dancing, cocktails and beer with Southie locals. Try their Pumpkin Martini with cinnamon or the gin, Aperol, St. Germain and lemon mixture that makes up the Seaport Sling. If you’re lucky enough to stumble in on a Sunday, you have a special treat coming your way in the form of Sinatra Sundays — Frank, all-night-long, need we say more?

  • Address: 355 Congress Street
  • Hours: Mon – Fri 11:30 a.m. – 2 a.m., Sat – Sun 10 a.m.-2 a.m.
  • Price: Cocktails $11-$12 and beers $3.50-$8




Photo courtesy of the Drink Facebook page.

Drink is a bar that hosts a cocktail party every night. With expert mixologists, you won’t be disappointed by the artful concoctions that the Drink staff will be shaking for you. Try whatever you want! No need for a menu at drink — tell the bartender what you feel like and they will whip up a delicious cocktail just for you!

  • Address: 348 Congress Street
  • Hours: Mon-Sun 4 p.m.- 1 a.m.
  • Price: $9-$14

What do you think of Southie as the new, safer, hip hangout? We know some locals are still hoping old Southie will resurface in South Boston, but it looks like SoBo is here to stay!

*feature image by Dale Cruse CC BY