10 places where you will discover the real Boston

Otherwise known as Little Italy, North End is one the city’s oldest residential neighbourhoods, and many of its best restaurants are family-owned. Don’t miss classic locations like Bricco or modern Italian flavours at Little Sage. A food tour is a great way to gain extra insight into the culinary culture of the neighbourhood and there are many on offer, including Secret Food Tours’ itinerary through the North End. With an expert guide, you will explore the Blackstone Block Historic District where you can dine in one of the USA’s oldest restaurants; the Boston Public Market; Little Italy with a chance to try its famous pizza, and you will learn about the Cannoli Wars while sampling the sweet treat for yourself.

Overindulged? Walk off any excesses with a stroll through the neighbourhood – it’s one of Boston’s oldest, and the architecture is stunning.

Boston’s public art includes the enormous, colourful murals you’ll see in Roxbury, where many pieces address issues such as civil rights and community. Head to the Rose Kennedy Greenway to admire everything from sculptures to light installations – artwork currently on display includes Jeffrey Gibson’s “your spirit whispering in my ear” which is about enduring challenges with faith, courage and strength, and Ja’Hari Ortega’s Big Hoops to Fill, which features two swings resembling golden hoop earrings. Equally diverse are the murals you’ll find in the gallery-packed South End neighbourhood.

Explored the Freedom Trail? Consider the Innovation Trail, which pays homage to hi-tech hotspots such as the MIT Museum, Draper Lab, the Museum of Medical History and Innovation at MassGeneral and the Moderna Building, where RNA vaccines for coronavirus were created. Other key spots include the place where Thomas Edison launched his career as an inventor, and where Alexander Graham Bell invented the telephone.

Jamaica Plain is a historic neighbourhood dating back to the 1800s, when streetcars rattled along its leafy avenues. It offers some interesting galleries and museums, including one which focuses on a more unusual subject matter – trees. Visit Harvard University’s Arnold Arboretum and you’ll find 281 acres filled with 15,000 plants, including some of the world’s rarest trees. The best way to explore it is on a guided tour.

The packed calendar of concerts and festivals is a reminder of the diversity of the city’s music scene. Its top live music venues include Grana for the Friday jazz sessions (although the cocktails alone make this bar worth a visit), Grace by Nia, a supper club-style venue in Seaport, Brighton’s Roadrunner venue, which has a capacity of 3,500, and the MGM Music Hall, which has hosted everyone from James Taylor to Bruno Mars. For cosier gigs, try Allston, which has numerous pubs which double as live music venues. One of the most famous examples is O’Brien’s Pub, a fabulously rough-and-ready dive bar at the heart of the city’s underground music scene.

Boston is truly a seafaring city, and there’s no better way to admire it than from the water. Kayaks can be hired from dozens of businesses lining the city’s harbour and its famous river, and there are plenty of guided tours for beginners. We recommend exploring both – opt for a kayak along the Charles River and you’ll get a whole new perspective on architectural gems such as the Hancock and Prudential Buildings and State House Dome, while harbour tours include a paddle around the Charlestown Navy Yard.

Beacon Hill has some of Boston’s most diverse architecture, much of which is in the historic district, laid out in the late 1700s. Must-sees include the Federal-style rowhouses, Massachusetts State House, with its golden dome, and the Boston Athenaeum, one of the oldest independent libraries in the US. Make sure you check out Cambridge Street’s Harrison Gray Otis House, famous for the neoclassical elements which adorn its façade. You’ll also see numerous examples of Greek Revival architecture, and one of the finest is Chestnut Street’s Otis-Cruft House, with its beautiful Ionic columns.

The best way to explore Chinatown is with a local – someone who can recommend the best markets, independent stores and local hangouts.  Jacqueline Church is a great example – she’s the founder of Boston Chinatown Tours, created to provide deep dives into the neighbourhood’s culinary scene with the help of visits to some of its oldest restaurants. You’ll also learn about its history, including the challenges faced by the early Chinese immigrants who shaped the area, whilst tasting and learning the traditions behind moon pies, dim sum and other delicacies from the independent traders who make up this vibrant community.

The SoWa (South Washington) neighbourhood is part of Boston’s South End. SoWa is especially well known for its eclectic art scene – it’s the city’s art and design district, and a place filled with gorgeous homeware boutiques, galleries and studios. Make sure you check out the SoWa market, which takes place every Sunday between May and October. Equally worthy of a visit is Thayer Street, lined with numerous artists’ studios – many of which are open to the public.

Perhaps Boston’s most beautiful museum is the Isabella Stewart Gardner Museum. Housed inside a Venetian-style palazzo, it is packed full of sculptures, paintings and other decorative arts, and it was founded by Isabella Stewart Gardner, a philanthropist and patron of the arts. There’s a packed calendar of events, and it’s not just the art which is spectacular – head to the courtyard to see breathtaking seasonal displays of plants from all over the world.

Art lovers should also check out the Institute of Contemporary Art, which has been exhibiting and educating on both national and international art since its founding in 1936. Although its 2006, multi-award winning building, cantilevered over the harbour is an icon of modern Boston architecture. 

Over at the Museum of Fine Arts, you can admire a collection of some 500,000 works that span ancient art to modern masterpieces. The Harvard Art Museum, meanwhile, boasts the beautifully restored Calderwood Courtyard, 50 art galleries and even an Art Study Center where you can make an appointment to see art that’s not on display.