Affectionately called "Southie,” South Boston is a neighborhood annexed to the city of Boston from 1804 to 1870, along with the Dorchester community farther south.
South Boston’s area, geographically an isthmus linking Dorchester to the mainland, expanded to 3.1 square miles over the years because of landfills.
This charming isthmus character still lives in Dorchester Heights, located in the central part of South Boston.
At this highest part of South Boston, visitors can enjoy overlooking views of Boston Harbor and the downtown district.
South Boston’s Dorchester Heights also marks a Revolutionary War site, enhancing its charms to visitors.
Besides the quaint glimpses of history that South Boston provides, it also offers many life and leisure attractions.
Check out some of these in the following list of the best things to do in South Boston, Massachusetts!
Explore Castle Island
This scenic island is on the northwestern waterfront of South Boston, accessible via William J. Day Boulevard.
Upon entry to Castle Island, the most prominent feature is the pentagonal Fort Independence that helped repulse the British attack on Boston during the War of 1812.
The island also features a monument to Donald McKay, the builder of the famed Sovereign of the Seas and Flying Cloud clipper ships.
South Boston service members who fought during the Korean War await tribute in a Castle Island memorial.
The other points of interest on the island are its picturesque Harborwalk and Causeway looping around its Pleasure Bay.
Visitors can enjoy swimming in the bay’s waters via either Castle Island Beach or the larger and sandier Pleasure Bay Beach.
Families with kids visiting Castle Island can bring their wards to a playground near the beach.
Similarly, Castle Island offers grassy slopes perfect for family activities like Frisbee throwing and small ball games.
Try fishing and watching the sailing ships at the pier on the northwestern edge of the island’s Fort Independence.
Pick a Playing Field at Joe Moakley Park
This 60-acre waterfront park spreads west of Columbia Road and adjoins Carson Beach.
Moakley Park started development in 1916, featuring various sports and recreational facilities.
Its sports arenas include three baseball diamonds, tennis courts, soccer fields, a track & field stadium, and a roller hockey rink.
Ten acres of the park have been reserved as a wooded grove and developed with walking trails with benches along the way.
Enjoy a Swim or a Walk on the I, L, and M Street Beaches
Located along Day Boulevard, these three beaches are farther south of Castle Island and named after the streets perpendicular to the coastline of Dorchester Bay.
Many prefer this three-mile-long stretch of the I, L, and M Street Beach over those on the island because they offer whiter sand, provide lifeguards, and have fewer jellyfish.
Besides swimming, these beaches are also ideal for sunbathing and strolls or biking along the shoreline.
A Harborwalk connects the pet-friendly I, L, and M Street beaches, which also offer picnic spots.
Take the Kids to the Dorothy Curran Children's Park
This kids’ playground is on Old Colony Avenue, adjacent to Moakley Park.
The Dorothy Curran Playground accommodates physically challenged children, with green principles also among its development guidelines.
Its ramps and flowing paths make this park wheelchair accessible, and soft surfacing was also used in the playground extensively.
Fragrant plants are part of the playground’s landscaping to help children with visual issues.
The playground’s equipment revolves around a nautical theme inspired by the Boston Harbor nearby.
Builders used recycled materials for the playground in keeping with the Dorothy Curran Children's Park's theme of sustainability.
Try the Polish Cuisine of Café Polonia
This restaurant on Dorchester Avenue claims as the only restaurant serving Polish cuisine in the greater Boston area.
Besides Polish dishes, Café Polonia also offers other Eastern European cuisine.
The comfort food on this restaurant’s menu includes Polish classics cheese pierogi, ravioli, and kielbasa.
Café Polonia further exudes charm in its unique décor and handcrafted furnishings, creating a cozy ambiance reminiscent of a mountain cottage in Poland.
Play Volleyball on Carson Beach
This crescent-shaped beach across Day Boulevard from Moakley Park is a popular destination for beach volleyball because of its vast, sandy shoreline.
Visitors of Carson Beach can also enjoy swimming, sunbathing, and taking strolls along the harbor walk that leads north to M Street Beach.
The 1925 bathhouse serving this beach added men's and women's bathrooms, three pavilions, and food and recreation stands in 1998.
Fascinating views of Thompson Island and Spectacle Island from Carson Beach, especially at sunset, help draw visitors to this beach.
Grab a Coffee at Esthetic Bean
Located on Preble Street, Esthetic Bean is a small but charming coffee shop that has grown to become a favorite of Southies.
They drop by here primarily for breakfast of Avocado toast and lavender latte from Esthetic Bean’s expert baristas.
Another popular choice in this coffee house is Frasier cake with fresh strawberries and light cream paired with iced coffee, with several flavors.
Delicious breakfast sandwiches, peanut butter banana milkshake, and lavender latte are also among the exquisite menu picks at Esthetic Bean.
Explore the Seaport District
Visitors who want a large concentration of waterfront bars and restaurants and other trendy points of interest should explore the Seaport District of South Boston.
This district, located immediately northwest of Castle Island, has undergone extensive redevelopment.
The Fan Pier Marina, with outdoor café tables, is one great stop in this district.
Nearby restaurants in this area include Mastro’s Ocean Club and Davio’s Northern Italian Steakhouse.
The district is also home to the park Lawn on D, next to the impressive Boston Convention & Exhibition Center.
Summer concerts and games, like ping-pong and bocce, are among the activities that draw visitors to this park.
Dine at Lincoln Tavern & Restaurant
This tavern and restaurant offer classic American food fare, including a wide selection of wood-fired-grilled meats.
Located on West Broadway, Lincoln Tavern & Restaurant opens patrons to delightful picks on appetizers like wood-fire-roasted spicy wings with blue cheese dressing.
It invites diners onward with the restaurant’s flagship Lincoln wood-grilled burger of a prime blend.
This sandwich comes with bacon aioli, Cabot sharp cheddar and caramelized French onions, all bundled in a house-made brioche sesame seed bun.
Diners at the Lincoln Tavern & Restaurant can grab a private booth or pick a spot at the lively main bar or the sit-down set-up in its back room.
Work up a Sweat at Rock Spot Climbing
This indoor, state-of-the-art rock-climbing facility on Old Colony Avenue in South Boston is one of three locations in Massachusetts.
Rock Spot Climbing in South Boston boasts a massive bouldering wall where climbers can pick from one of its eight sections, with routes reset weekly for variations in challenges.
This facility also offers four main top rope set-ups, with each section presenting between seven to 20 routes.
Rock Spot Climbing provides auto belay systems enabling novice climbers to scale their walls within minutes after a brief safety orientation.
Tour the Museums at Fort Point
The Fort Point Channel Landmark District, South Boston’s historic industrial waterfront, offers many learning opportunities in its museums on Congress Street.
Boston Tea Party Ships & Museum is worth visiting here, with its multimedia exhibits and reenactments.
Later, you can tour the Boston Children's Museum featuring educational, hands-on exhibits for kids.
Then, stop by the Boston Fire Museum in an old firehouse featuring displays about Boston's firefighting history.
The Fort Point Channel Landmark District encompasses 55 acres, developed in the 1830s.
Its late 19th and early 20th-century industrial loft buildings represent Boston’s most extensive and most cohesive collection.
Make a historical day of it at Fort Point!
Have a Beer at Trillium Brewing Company
The award-winning Trillium Brewing Company operates a location in South Boston’s Fort Point.
This watering hole is on Thomson Place and provides a two-floor taproom and a full-service restaurant with a casual setting.
Weather permitting, customers can also enjoy their beers and food on Trillium Fort Point’s patio or roof deck.
Take the Kids to Martin’s Park
Another attraction in the Fort Point Channel Landmark District is Martin’s Park on Sleeper Street near Boston’s Children's Museum.
Children of all abilities can enjoy this park’s various creative playground structures, such as a play ship with a talk tube.
The park’s playground also features a tube, embankment slides, a log climber, a climbing hill, and a rope climbing setup.
Visitors of this park can also connect with nature in its herb and sunflower gardens and learn about the stone, plants, and wood used in Martin’s Park.
Martin's Park opens from dawn to dusk.
Celebrate St. Patrick’s Day with the St. Patrick’s Day Parade
South Boston celebrates its Irish heritage with the grand St. Patrick’s Day Parade set on the Sunday closest to March 17, the feast day of Ireland’s patron saint.
On this day, South Boston also marks Evacuation Day to commemorate the pullout of British troops from Boston on March 17, 1776.
The crowds of thousands who attend these dual celebrations see colorful floats and marching bands.
St. Patrick’s Day in South Boston is also a time for concerts, Irish food and music, pub activities, and cruises.
Book a Cruise or Fishing Charter with Classic Sail Boston
Cruising and boating, as well as fishing, are ingrained in South Boston, as seen in its famous Seaport District.
For cruises, Classic Sail Boston on Webster Street is one of the top-rated picks, with its three choices on boat charters.
Classic Sail Boston offers a two-hour private charter that sails around the inner Boston Harbor for amazing views of Boston’s best.
This trip will take you to the coastal waters off Seaport, Castle Island, Southie, Spectacle Island, Charlestown, Eastie, and the North End.
Take the four-hour, half-day private charter if you want an extended cruise to the Boston Harbor Islands.
To explore the islands and their lighthouses, book a full-day private charter during which you can also enjoy a swim besides island-hopping.
Many boat rentals are also available to anglers at South Boston’s Seaport District, with operators knowledgeable on local fishing grounds.
Some shops in this district likewise sell fishing gear like bait and tackle.
Enjoy a Comedy Act at Laugh Boston
Laugh Boston is a 16+ club in the lobby of the Westin Hotel in the Seaport District.
Nationally touring headline comedy acts and local comedians perform in this club’s 300-seat, state-of-the-art venue.
The programming of Laugh Boston changes weekly, and updates are available on its website’s calendar of events.
Grab the required two-item minimum order of food/drink before seeing a Laugh Boston performance.
Visit the Institute of Contemporary Art
The Institute of Contemporary Art, founded as the Boston Museum of Modern Art in 1936, is a prestigious exhibition space and art museum.
It moved in 2006 to its current location on Harbor Shore Drive in South Boston’s Seaport District.
The institute’s 65,000-square-foot building melds interior and exterior space, allowing shifting waterfront perspectives throughout its galleries, performance space, and public areas.
The exhibition program here includes works of emerging artists, Boston-area artists, and commissioned artistic talents.
The institute hosts performances in an outdoor amphitheater overlooking Boston Harbor.
The Institute of Contemporary Art is open to the public.
South Boston and its vibrant waterfront districts deserve top billing in an itinerary on a trip to the city of Boston.
These points of interest combine the whole gamut of lifestyles and claims that may very well define the essence of the city of Boston itself.
Plan your trip today and discover the best things to do in South Boston!