Image courtesy of David Fox

1. Classic Boston: Downtown

Even if you’re a cutting-edge traveller, it would be unfair to deny yourself the city’s classic attractions. Explore downtown’s historic heart by following the clearly marked “Freedom Trail,” a crash course in American history. The stately colonial buildings along the hilly path will immerse you in Boston’s classic atmosphere. Meander from the lively Faneuil Hall Marketplace to the gilt-domed State House. Along the way you’ll fall in love with North End’s Little Italy and the cobblestone streets of Beacon Hill, the home of New England’s elite where gas lanterns continue to illuminate the brick façades of charming townhouses. When you’re ready for a break, head to Boston Common, the city’s central park where tulips and willow trees bring briefcase-toting business folk together with the Frisbee set.


Hotel Revere

(617) 482-1800

The 24-story hotel strategically placed between Boston Common and the South End features 365 stylish guestrooms that marry classic coffee-coloured furniture with surprising contemporary sculptures. After a long day hitting the pavement, relax with a drink at the dramatically illuminated Emerald Lounge.

Union Oyster House
41 Union Street
(617) 227-2750

John F. Kennedy may have had his favourite booth here, but the real action is at the circular counter, where you watch the kitchen staff shuck oysters at an astonishing speed. At 187-years-old, this place is the longest running restaurant in the U.S. Oysters may be the main attraction, but don’t forget the classic New England clam chowder, too.

Black book travel guide: The best addresses to visit in LOS ANGELES

69 Church St.,
(617) 426-6969

Often voted by the locals as the city’s best Italian chef, Erbaluce’s Charles Draghi puts out a nightly changing menu of fragrant, herb-driven fares made with Old World patience.

2. Stylish Boston: Back Bay & South End

Boston isn’t a stuffy Puritan hamlet, and the proof lies in the stylish neighbourhood South End. Traditionally a gaybourhood, South End is now an indisputable style center that combines delightful Victorian architecture with decidedly un-Victorian openness. A quick cab ride away is Back Bay, where more established businesses occupy the neat checkerboard of Gilded Age row houses. Strut down the 220-foot-wide thoroughfare of Commonwealth Avenue that comes alive with magnolia and blooming dogwood trees in spring. Next to it, Newbury Street boasts an eclectic mix of spas, shops, chain stores and other attractions.

Travel guide: FASHION CAPITALS of the world


505 Tremont Street
(617) 536-0809
sookiboston.comA women’s clothing shop that stocks young up-start designers as well as one-of-a-kind dresses from Europe and Japan.

Bobby from Boston

19 Thayer Street
(617) 423-9299

This South End gem focuses on men’s vintage clothes but also has a small, tasteful women’s section. Even if you decide against that Mad Men-esque briefcase or tailored shorts, this impeccably curated shop is a delightful experience.

For more stylish addresses in Boston, click through to the next page… 

Image courtesy of Tim Grafft/MOTT

SoWa Open Market

540 Harrison Avenue

(617) 481-2257

Celebrating its tenth year, this Sunday market brings clothiers and jewelers to show off their creative endeavors next to artisan food makers.

Travel guide: Chic places to visit in SAN FRANCISCO

Hammersley’s Bistro
553 Tremont St
(617) 423-2700,

Rustic New England ingredients get a French makeover in the open kitchen of this inviting eatery. The simple chicken, roasted to perfection, has put this chic eatery on the culinary radar of many picky eaters.

3. Off the beaten path Boston: Somerville

Somerville was long overshadowed by its more bookish and famous neighbor, Cambridge, home of Harvard. Thanks to an influx of young creative types, however, Somerville is prepping itself for the prime time. Davis Square, humming with life along the thoroughfare of Elm Street, is on the Red Line; Inman and Union squares, still rough around the edges, can be reached by bus 69 from Harvard Square (until the new subway line is completed, that is).

Travel guide: The top travel HOTS SPOTS IN TORONTO 


561 Windsor Street
(617) 623-0804

The tiny chocolatier has made a name for itself with its delectable products, like stone-ground bars and drinkable salted almond chocolate. Free samples and $5 guided tours available.

The Independent
75 Union Square
(617) 440-6022

A young pub with a DJ and yummy bar food, this watering hole is one of the most down-to-earth and fun places for a night out with the locals and students.

Travel guide: Eat, drink and go out in NEW YORK CITY

Bloc 11
11 Bow St
(617) 623-0000

Once an old bank, the five-year-old café is Union Square’s beloved neighbourhood joint, hosting occasional pop-up dining events as well.

Grillo’s Pickle

1075 Cambridge St
[no phone]

The surefire sign of hipsterdom and gentrification has arrived in Inman Square—in the form of an artisan pickle shop selling the likes of spicy asparagus and marinated grapes. Next door is a from-scratch “Food Lab,” Clover Hub.

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