Get to know Boston via its South End and Seaport

So you’ve done the Freedom Trail and the Duck Boats and Harvard Square, and you think you know Boston, right? I get it: I lived in and around Boston for part of my childhood and go back frequently, since I have family all over Massachusetts. I thought I knew Boston, too. But now it’s time to see a new side of Beantown, as The WeekEnder takes you to two hot neighborhoods—the South End and the Seaport—and introduces you to four Bostonians who will help guide the way.

Nia Grace owns a pair of glamorous supper clubs in these two neighborhoods: Grace by Nia in the Seaport and Darryl’s Corner Bar & Kitchen in the South End. So she has the ideal perspective on what sets these areas apart—and brings them together. “The South End is that perfect blend of old New England and the nouveau life: It’s so nostalgic and quaint and rich in history,” says Grace. “Then when you go down to the Seaport, it’s the new thing that’s going to one day be a part of history. It’s like the tale of two cities, for real.”

For Grace, launching a 5,000-square-foot restaurant in the Seaport means coming full circle: As a teenager she worked on the Spirit of Boston, a dinner cruise yacht, when the waterfront was nothing like it is today. “The only thing down here was that boat, a few restaurants, and tons and tons of parking lots,” says Grace.

Over the past decade or so, this former industrial wasteland has been transformed into a buzzing neighborhood that’s also known as—fittingly—the Innovation District, where gleaming modern architecture is set against the backdrop of Boston Harbor. Alison Barnard O’Brien decided to open the flagship of her cutting-edge denim brand, In-jean-ius, here. “I was drawn by the water,” she says. “Although Boston is on the water, there hasn’t been a big waterfront experience in other neighborhoods—until now.”

Not far from the Seaport is the South End, one of the largest urban Victorian neighborhoods in the country and once home to Martin Luther King, Jr. and Coretta Scott King. James Beard Award-winning chef Joanne Chang has several restaurants in the area, including Myers + Chang (which serves elevated versions of street food from around Asia) and Flour Bakery + Cafe (whose sticky buns helped put the South End on the food radar). When Chang opened her first outpost of Flour back in 2000, the area had a dirt road running through it. She loved the history and the diversity that still exists today. “The South End encompasses a lot of different types of people,” she says. “There’s some lower income housing, there are million dollar condos, it’s gay, it’s straight, it’s everything.”

And of course, there’s that quintessential Bostonian charm, points out Connie Shaheen, general manager of the South End’s Revolution Hotel. “When you think of Boston, you’re picturing the rows of brownstones, the tree-lined streets, and the quaint Brahman style that makes up this neighborhood,” she says.

In this edition of The WeekEnder, I’m excited to share recommendations from these plugged-in experts (as well as a few tips of my own) for a weekend escape that’s rich in history but also alive with renewal and progress—the very essence of Boston itself.

In these two neighborhoods, a hotel stay is more than just a place to rest; it’s part of the experience.

You can’t beat this hotel’s location—or the stunning panoramas of the harbor from its stylish rooms and rooftop bar (more on that in a few). “It’s at the entrance of the Seaport, and you can easily get to any other parts of the city,” says O’Brien.

Inspired by Boston’s vibrant art scene, the Omni is filled with paintings, sculptures, and digital installations—thanks to a partnership with the nearby Institute of Contemporary Art.

This hip boutique hotel in a former YMCA building honors the city’s rich history, with lyrics from Boston bands (Aerosmith, the Cars) on the walls in the rooms and artwork in the lobby celebrating local inventions like the sewing machine.

Rooms are small but clean, with a surprising level of style, considering the price.

Between the Seaport and the South End, there are endless food options—from seafood shacks to fine dining. Here are a few spots to put on your must-eat list.

Cafe Tatte in the Seaport – This coffee bar specializes in Mediterranean-style breakfast favorites like pistachio croissants, shakshuka, and Greek pancakes.

Flour Bakery + Cafe in the South End – Flour’s sticky buns had a starring role on Bobby Flay’s Throwdown, and its egg sandwiches have just as much of a cult following. But owner Joanne Chang had humble goals when she opened her first location: “What we wanted to do—and still want to do—is to be a neighborhood hangout, the bakery form of Cheers where everybody knows your name.”

Barking Crab in the Seaport – With its picnic tables under a yellow-and-red striped tent, the Barking Crab channels a coastal clam shack. “It’s a Boston institution for fried seafood and it can get packed,” says O’Brien.

Yankee Lobster in the Seaport – For your lobster roll fix. “If I’m on a quick and casual seafood hunt, Yankee Lobster never fails. I get my lobster roll hot and buttered,” says Grace. “They also have some of the best clam bellies in the city.”

B&G Oysters in the South End – Acclaimed chef Barbara Lynch runs this South End seafood mainstay. “One of the best lobster rolls in town, if you’re looking for a quintessential Boston thing that you can check off your list,” says Shaheen.

Para Maria in the Seaport – Dishes here are inspired by chef Tatiana Pairot Rosana’s Cuban background together with influences from her wife’s Korean heritage. Think Korean beef tacos with kimchi, green onions, and togarashi. Fun fact: Rosana won Food Network’s Chopped twice.

Myers + Chang in the South End – At this neighborhood favorite, Chang mixes influences from all over Asia: Taiwan, China, Thailand, Vietnam, Indonesia. Some of the hit dishes include the tea-smoked ribs, the pork belly buns, the lemongrass mussels, and a scallion pancake made with pizza dough from Flour Bakery.

Shore Leave in the South End – Talk about fusion: Shore Leave combines a tiki bar experience with a great sushi selection. “This is where I want to be every night for the rest of winter because you feel like you’re somewhere tropical,” says Shaheen.

Woods Hill Pier 4 in the Seaport – “At this woman-owned spot, everything is farm-to-table—with the exception of seafood, obviously” says O’Brien. “You can’t have a bad meal.”

Bootleg Special in the South End – “This warehouse-chic Creole-style restaurant does crab boils, which isn’t something that Boston ever had,” says Shaheen.

Coppa in the South End – “A tiny little Italian restaurant—I just went there for my birthday a couple months ago. They serve excellent pizzas and pasta,” says Chang.

Grace by Nia in the Seaport – Soul-meets-the-Seaport at this modern-day supperclub with live jazz. Grace recommends the bourbon peach spare ribs garnished with fresh grilled peaches, the molasses-braised oxtails with coconut grits, and the “unfashioned” (a twist on an old-fashioned cocktail with amaro and brown sugar simple syrup).

Committee in the Seaport – Craft cocktails and creative mezes like octopus with olive tapenade and pepper coulis set the scene at this restaurant inspired by Greek ouzeri (upscale tavernas).

Darryl’s Corner Bar & Kitchen in the South End – Warm hospitality, smooth jazz, and a menu that spotlights Southern cuisine with a modern twist. Think fried catfish with Cajun remoulade, sauteed calamari with a clover honey and fresh garlic sauce.

Wink & Nod in the South End – “A speakeasy-style restaurant with a heavy focus on cocktails. You can spend the night trying all the small plates,” says Shaheen. “It’s a hidden gem.”

Lookout Rooftop and Bar in the Seaport – This bar atop the Envoy hotel has skyline and harbor views, fire pits, and igloo pop-ups in winter.

Beehive in the South End – A bohemian-style collegiate favorite with live music almost every night of the week and killer cocktails. “It’s a staple in the South End and a uniquely Boston experience,” says Shaheen.

In the Seaport and the South End, the art scene reflects the diverse and ever-evolving spirit of Boston.

Institute of Contemporary Art (ICA) in the Seaport – Founded as a sister to New York’s Museum of Modern Art (MoMA), the ICA is on the cutting edge of art, with programming that goes beyond what’s on the walls—film, dance, DJ parties, and more. “I love what they do. They have really pushed the limits in terms of what museum programming can be like,” says Grace.

Self Guided Neighborhood Art Walk in the Seaport – Stroll around and take in all the public artwork in the Seaport, from an abstract painting by Frank Stella to bold murals by up-and-coming local painters.

Breathe Life in the South End – Don’t miss this mural series from Rob Gibbs, a.k.a. ProBlak. “Rob’s art is accessible to all and relatable to everybody who looks at it,” says Grace. “He is breathing life throughout this entire city with his street art.”

Wally’s Cafe Jazz Club in the South End – “No visit to Boston is complete—especially if you’re a music lover—without visiting Wally’s, the oldest family-owned jazz club in the nation and the first African-American owned nightclub in New England,” says Grace.

It may be a city, but between urban spots Boston offers plenty of calm green spaces. Here are a few of our picks.

Fan Pier Park in the Seaport – This old pier has been transformed into a sprawling park with outstanding views of the Boston skyline.

Harbor Way in the Seaport – Up for a little bouldering in the middle of the city? Check out the Rocks at Harbor Way, where you can sit or climb on locally sourced boulders. And coming in 2024: a pedestrian promenade that will change the way the Seaport connects to Boston Harbor.

Peters Park in the South End – “A huge park with basketball, tennis, and a mural commissioned by a local hip-hop artist,” says Chang.

Incredible food, crafts, custom sneakers, plus holiday markets—the shops here reflect their eclectic and buzzy neighborhoods.

In-jean-ius in the Seaport – Whether you’re looking for bootcut, stovepipe, or skinny jeans, this place has you covered. “The store environment is very friendly. Even if the people shopping here don’t know each other, they always seem to make friends in the fitting room,” says O’Brien.

Snowport in the Seaport – This annual winter wonderland launching on November 10 includes a European-style holiday market and bedazzled, holiday-themed pop-up bars.

The Current in the Seaport – This shopping village is an incubation space for up-and-coming retailers plus some names you know—check out “Converse By You,” where you can customize a pair of sneakers.

Formaggio Kitchen in the South End – “The very best food store,” says Chang. “Formaggio is well known for its cheese as well as excellent snacks like fancy nuts and chips and candies—everything you want to eat.”

Michele Mercaldo in the South End – “Michelle does her own jewelry and showcases a number of beautiful designers,” says Chang. “My husband’s wedding ring is from her. And I have a number of necklaces and earrings. Beautiful silver and gold and stonework.”

SoWa Winter Festival in the South End – A seasonal artisan crafts market in a restored electrical factory runs on weekends from November 24 through December 17. “They do a great job of highlighting local artists and craftsmen,” says Shaheen. (Heads up: It returns as the SoWa Open Market on May 7 and runs on Sundays through October.)