The insider’s guide to Boston: The old soul of New England

Where cobblestones meet cutting-edge culture, Boston’s storied past and dynamic present create a city experience rich in heritage, style and spirit.

Boston Tea Party Ships & Museum

Boston is known as the ‘birthplace of the American Revolution’, and this immersive museum is a top spot to understand why 342 chests of tea, valued at approximately AU$2.65 million in today’s currency, were tossed into Boston Harbour in December 1773.

Beacon Hill

Home of the glorious golden-domed State House and a labyrinth of narrow streets lined with elegant, Federal-style buildings and original gas lamps, this swanky neighbourhood is so well preserved it’s like stepping into a movie set – literally. Cobbled Acorn Street is one of the most photographed streets in the USA.

Freedom Trail

American history in a nutshell is as simple as following the ‘red brick road’. Weaving four kilometres through Boston’s neighbourhoods, your route marked by a red line, the Freedom Trail links 16 significant historic sites including the poignant Granary Burying Ground, Paul Revere House – the oldest remaining structure in the city – and Faneuil Hall, commonly called the ‘Cradle of Liberty’. Walk the trail at your own pace or join a guided tour, often led by actors.

Isabella Stewart Gardner Museum

Founded by its philanthropist art collector namesake between 1900 and 1902, this stunning four-storey Italianate-style building is one of Boston’s greatest treasures. Home to Gardner’s lifetime collection, it features works by iconic artists Rembrandt, Degas, Raphael, Manet, Michelangelo, Matisse and Titan, gracing spaces through a series of galleries overlooking a magnificent courtyard featuring Australian tree ferns. On her death, Gardner bequeathed the museum to the city of Boston on one condition – it always remains as she left it. gardnermuseum.org

O Ya

Set in a century-old fire station in Boston’s vibrant Leather District, O Ya’s vibe is at once intimate yet radiates curiosity. Japanese cuisine with a twist, the nightly 20-course omakase is pure genius. Expect the unexpected and book way ahead – it’s a dining experience you’ll be talking about for years to come. o-ya.restaurant

Neptune Oyster

Seafood is synonymous with Boston, and this hole-in-the-wall restaurant tucked into the North End is the go-to place for everything from oysters shucked while you wait to lobster rolls, smoked bluefish, clambake and bluefin tuna. Perch on a stool at the classic marble-topped bar or sink into a red banquette at one of the cosy tables. With a no reservations policy, prepare to queue. neptuneoyster.com

Lenox Sophia

This local’s haunt in buzzy South Boston serves creative American fare offering an omnivore or vegetarian five-course prix-fixe menu four nights a week. With a fine pedigree including The French Laundry and Bouchon, owner and chef Shi Mei welcomes diners into his 16-seat restaurant as if it’s his home – so much so you can even BYO wine and beer. lenoxsophia.com

Natural Beauty

Nature is on the doorstep of every Bostonian. Known as the Emerald Necklace, a chain of outdoor spaces wraps around the city’s neighbourhoods, including walking trails, bike tracks, parks, golf courses, ponds, forests, an arboretum and the most treasured jewel: Boston Common. Dating back to 1634 when Bostonians voted to pay a one-off tax to create a free communal space downtown, the 20-hectare park, together with the adjoining Boston Public Gardens, is the perfect place to feel connected to nature.

The Lenox Hotel

Built in Beaux-Arts style in 1900, this grande dame of Boston has not only stood the test of time – she’s thrived. The location on the corner of Exeter and Boylston streets in classy Back Bay is hard to fault, with the best of the city just footsteps away. Throughout the 214 rooms, style and service is at the forefront. Book accommodations with a fireplace and staff will organise to have your room cosy and warm when you return home after a day of sightseeing. lenoxhotel.com

Raffles Boston

Shiny and new in 2023, Raffles Boston’s 35-storey glass tower is the Singapore-based company’s first foray into North America. From the variation-on-a-classic-themed ‘Boston Sling’ welcome drink to the 147 opulent rooms complete with meticulous butler service and tech-savvy touches like electronic blackout shades for long summer nights, everything about this stylish newbie screams elegance. raffles.com

Boston rates top of the pops on walkability scales. The majority of attractions are easily accessed on foot or bike, and there is a raft of trails to explore, whether on your own or with a guide. The subway, known as ‘the T’, is cleverly colour-coded to suit the environment, such as green for the park system and blue for areas near the ocean. Hop on a ferry to explore the Boston Harbor Islands National and State Park.