How to Spend a 3-Day Vacation in Boston

Walk the Freedom Trail, eat award-winning chowder and see penguins. All that is just the first day.

Photograph by Sean Pavone/iStock

Founded in 1630, Boston is one of North America’s oldest cities, resulting in a whole host of historic landmarks; downtown is home to some of the United States oldest parks, cemeteries and taverns, while the North End mixes colonial architecture with old-world Italian charm. There’s also an eclectic mix of neighbourhoods, from Fenway-Kenmore’s 1970s rock scene to Beacon Hill’s African-American legacy, that are best explored on foot.

Day 1


Fanueil Hall Marketplace (left) and Paramount Theatre (bottom right) by Stan Tess/Alamy. New England Aquarium (top right) by Marcus Baker/Alamy.


Morning Explore downtown Boston by walking the four-kilometre self-guided Freedom Trail. Starting at the Boston Common, follow the path’s red bricks to historic sites like Old State House and the Granary Burying Ground, where figures from the Revolutionary War are buried.

Afternoon Continue along the trail to Faneuil Hall Marketplace to browse its many shops and restaurants. Try Boston Chowda Co.’s award-winning namesake, grab a pint at J.J. Donovan’s Irish tavern, then leave the Freedom Trail and walk five minutes along the harbour to see penguins, seals and sharks at the New England Aquarium.

Evening Walk 20 minutes south of the market, through the public art-filled Rose Fitzgerald Kennedy Greenway, to Chinatown to try gourmet Cantonese fare such as Peking duck ravioli or fresh ginger lobster stir-fry at Peach Farm restaurant. End the evening by taking in a performance at the Boston Opera House or the vaudeville-era Paramount Theatre.

Day 2


Photograph by Joyelle West.


Morning Start the day in Back Bay shopping on Newbury Street where eight blocks of high-end shops, boutiques and pop-ups fill the 19th-century Victorian brownstones. Don’t miss Newbury Comics, a Boston pop culture institution with exclusive vinyl and graphic novels.

Afternoon Afterwards, head over to Copley Square for a tour of Trinity Church, a beautiful Boston landmark built in 1877 featuring incredible stained-glass windows, heavy arches and a dramatic tower. Cross the square to the Boston Public Library for afternoon tea with smoked salmon sandwiches and macarons in its dining room overlooking the Italian Courtyard.

Evening Continue down the street to Fenway-Kenmore’s Hojoko, a funky Japanese tavern in The Verb Hotel. Share the wasabi roulette where one super-spicy roll is hidden amidst sushi pieces. After dinner, check out local music memorabilia from Aerosmith and The J. Geils Band in the hotel lobby, then catch a concert at a nearby venue like House of Blues.

Day 3


Photograph by Sean Pavone/Alamy


Morning Immerse yourself in the North End’s American Revolution history at the Old North Church, where patriot Paul Revere’s associates hung the lanterns that signalled the British were invading. Next, walk down Hanover Street for the Great Gatsby themed brunch at Parla—don’t miss the meatball and fontina baguette.

Afternoon Visit Beacon Hill’s Museum of African American History to learn about the neighbourhood’s role in ending slavery—many freed slaves in Boston lived in Beacon Hill between 1800 and 1900 and participated in the Underground Railroad. Wander the neighourhood’s cobblestoned streets and admire the 19th-century brick row houses, including 66 Phillips Street, a former Underground Railroad station.

Evening Stroll down Beacon Street, passing by the gold-domed Massachusetts State House, and head for supper at Carrie Nation. The cheeky prohibition-inspired restaurant serves dishes such as pan-seared salmon with saffron leeks and lamb osso buco. Find the restaurant’s hidden speakeasy (spoiler: it’s at the back of the restaurant) for cocktails like the Boston Mahatma made with Irish whiskey, orange marmalade and egg white.


Bonus: Stop in at Cheers

Cheers bar, featured in the eponymous TV sitcom, is located in Boston’s Beacon Hill neighbourhood. Drop by for a pint and a Giant Norm Burger.



[This story appears in the march 2018 issue of WestJet Magazine and has since been updated.]