When English Puritans arrived on the Mayflower in the early 17th century, the land that would become New England swiftly proved itself to be self-sufficient and the colonies extended out from Plymouth to Salem, Gloucester, and the now capital of Massachusetts, Boston. Now celebrating its 390th birthday, Boston is a much-beloved US city that has a rich history, a competitive sports scene, and a unique culture that is unlike any other state capital.
Eighty-four sub-districts make up the twenty-three officially designated Boston neighborhoods, so for anyone planning a vacation or weekend getaway to the city there are plenty of options for local attractions, sightseeing experiences, and amazing restaurants. But where to begin? To narrow the field, we’ve put together a list of our top ten things to do in Boston across our favorite neighborhoods, so you can prioritize your interests and make the most of your time. From kayaking the Charles River to Back Bay wine tasting, there’s something for everyone in Boston, MA.
| North End
Unlike almost every other city in America, Boston doesn’t have a defined ‘Downtown’ neighborhood. It doesn’t even have a particularly distinct historic district, although many will tell you Beacon Hill (where you’ll find the Cheers bar), is the best spot for Boston history.
What it does have is North End, a neighborhood that features a large portion of the Freedom Trail, Boston’s Little Italy, and the immensely popular Paul Revere House. The best way to explore this area? On a pizza tasting tour of course! Join a local guide and visit key sites along the Freedom Trail, plus slices of pizza at three of the best establishments in the region. Our favorite Boston sightseeing experience for foodies!
| West End
The West End is a small mostly non-residential neighborhood that acts as a gateway to Kendall Square, East Cambridge and Bunker Hill across several bridges, including the iconic Leonard P. Zakim Bunker Hill Memorial Bridge.
Further south on the Charles River Dam Road is the Boston Museum of Science, a sprawling monument to the world of science with exhibits on space, technology, animals, and loads more. Kids will love the Butterfly Garden, the Hall of Human Life and the dinosaur fossils, but the museum also hosts Adult Events for the grown-ups, with regular artistic Planetarium experiences, podcast tapings and gaming sessions after hours. The Museum of Science is the ultimate day out on a Boston family vacation!
| South Boston
When you research what Boston is known for, food dishes like baked beans and clam chowder often appear, plus the mighty lobster roll. So next question is, where do you find the best? Many will claim to serve Boston’s best lobster roll, but we’re sticking with our favorite at Row 34 in South Boston.
Across the Fort Point Channel and nestled amongst The Institute of Contemporary Art, Boston Children's Museum, and the Boston Convention and Exhibition Center, Row 34 is a professionals-only warehouse-style bar and restaurant where you can pick up a warm buttered lobster roll or the famous Ethel's Creamy Lobster, served with their signature slaw and chips. Lobster doesn’t get much classier than this!
| Charlestown
If you’re looking for Boston history, Charlestown is where you’ll find it. Boston’s oldest neighborhood was settled in 1629 and engineered by Thomas Graves during the reign of King Charles I of England (hence the name).
At the start of the American Revolutionary War, Charlestown was the site of the famous Battle of Bunker Hill in 1775, which saw hundreds of British and colonial troops wounded or killed.
Fifty years later construction of the Bunker Hill Monument started, and seventeen years after that the 221-foot granite obelisk was complete. Head to Charlestown and admire the William Prescott Statue, visit the Bunker Hill Museum, and even climb the Monument via the Bunker Hill Lodge, an exciting experience for American history buffs!
| Fenway–Kenmore
A highly popular Boston neighborhood for visitors is Fenway–Kenmore, home to the Red Sox baseball team at the iconic Fenway Park stadium. Although baseball games and sports bars are the main draw, Fenway-Kenmore also houses the Museum of Fine Arts, the Mary Baker Eddy Library, and the beautiful Fenway Garden Society, making it a great destination for culture seekers and sports fans alike.
Baseball season generally runs between April and October so you should definitely grab a game ticket if you’re visiting in summer, but Fenway Park is also open for tours and events throughout the year (top tip - Thornton's Fenway Grille does 25¢ chicken wings and $5 margaritas on non-game days!).
| Back Bay
Bordering Fenway-Kenmore is the Back Bay neighborhood, an upper class shopping district known for its stylish restaurants. Get an epic view of the Boston skyline and Charles River at the Skywalk Observatory deck, stroll along the Commonwealth Avenue Mall, or partake in our favorite Back Bay activity, the Boston wine tasting tour.
Experience how the affluent residents wind down with a tour round the neighborhood’s best wine bars and tasting rooms, letting a knowledgeable guide regale you with entertaining commentary and local trivia. Learn how to taste wine like a pro on a girly night out or treat a wine lover to a thoughtful experience gift certificate!
| South End
Not to be confused with South Boston, the South End and South of Washington neighborhoods comprise the city’s arts and design district, packed with galleries, studios, and global restaurants where hipsters and students gather in droves. If you’re going to be in Boston over the weekend, a trip to the SoWa Open Market is an absolute must.
The main market operates every Sunday between May and October, with a weekly craft brewery tap takeover in the beer garden, art exhibitions from local artists, a range of food trucks for every appetite, and groceries from independent farmers. In the winter you can catch the SoWa Winter Festival, and the SoWa Farmers Market and SoWa Vintage Market operate throughout the year!
| Egleston Square
Take the Orange Line thirty minutes out from North End and you reach Egleston Square, a relatively industrial, nondescript neighborhood that may seem an odd choice for a Boston destination guide, until you learn the Samuel Adams brewery is located here.
Sam Adams is a Boston national treasure so a trip to the brewery is exciting enough for any beer lover, but just to make the journey even more worthwhile, brewery tours are completely free! An expert brewer will take you round the back-of-house to explore the fermentation process, ingredients, and brewing techniques before offering three samples to try, and a tasting glass to take home. We guarantee this is a Boston experience that’s worth the trip!
| Kendall Square
Cross the Charles River from Beacon Hill via the Longfellow Bridge and you reach Kendall Square, a neighborhood built around the famed Massachusetts Institute of Technology.
You can do a free self-guided tour of the MIT campus, but if you’ve done enough walking for the day booking a scenic Boston Harbor Kayak Tour is a relaxing alternative to traditional sightseeing. Launching from the Broad Canal in Kendall Square, the three-hour tour paddles along the Boston Waterfront, past the USS Constitution, North Point Park, Charles River Dam, the Zakim Bridge, and many more Boston landmarks. Charles River kayaking is a tranquil experience that everyone can enjoy!
| Waterfront
On the harbor side of Boston’s Financial District is the Waterfront neighborhood, a stretch of upmarket properties, seafood restaurants, and the popular New England Aquarium.
The wharfs and ferry terminals that line the Waterfront host a variety of sightseeing cruise companies, but our favorite is the Boston Whale Watching Tour. Whale season is between April and November and cruises depart daily, with fascinating commentary from an on-board Naturalist throughout the tour. You’ll learn all about conservation, tracking, and migration and hopefully spot some majestic whales and dolphins in the Stellwagen Bank National Marine Sanctuary – this is a truly unique Boston sightseeing experience!
| Thanks for Reading!
With eighty-four sub-districts in total, these top ten Boston neighborhoods only scratch the surface when it comes to days out, activities and experiences in the vast city. From weekend trips with your best buds to family vacations, there’s something for every budget and personality in Boston. Let us know what you think in the comments below!
