Just north of busy downtown, this stretch of Yonge Street is lined with tony boutiques and chic cafés catering to residents of two of the city’s most affluent neighbourhoods.

Advice from a Caterpillar

TIMELESS FOR TOTS Inspired by author Lewis Carroll, Advice From a Caterpillar is a wonderland of clothes, books, toys and furniture for newborns to six-year-olds. The whimsically decorated boutique is the only shop in Canada to offer French brands Bonton and L’Esprit de Luna. It also has a smattering of unique vintage items, some dating to the early 1900s.

DESIGNER HUB The elegant interior of The Narwhal Boutique, complete with Persian rugs and a Victorian chandelier, contrasts nicely with the modern clothes on the racks. Though somewhat tucked away, it’s a hot spot for women seeking New York–chic labels plus designs from Scandinavia.

Gee Beauty

SUPERB SALON Book some time to get glamorous at Gee Beauty. The chic makeup and skincare studio offers sought-after services including mani-pedis, facials and brow shaping, and even sells its own line of cosmetics. Men, too, are treated like movie stars here, with grooming options like the “Sean Connery” and the “Cool Hand Luke.”

UPSCALE INTERIOR Two-level home decor store Hollace Cluny is so perfectly appointed, you may find yourself wishing you could just to move in. Furniture, lighting, home accents and more by a long list of Canadian and international designers—from Alvar Aalto to Martha Sturdy—are all here to help enhance your own living space.

Golden Mint Coffee & Tea Company

DRINKS FOR ALL Although Golden Mint Coffee & Tea Company offers a range of espresso-based beverages and more than 150 loose-leaf teas, it’s hard to ignore the assortment of handmade truffles and delicious Belgian chocolate–covered caramel apples behind the glass counter. Take a time out with one of these treats, a fresh panini, or a real-fruit smoothie, too.

LOCAL LOVE Noted chef Kevin McKenna creates breezily sophisticated lunch, brunch and dinner dishes at Earth Rosedale. Among the many must-try menu items are wood-oven flatbreads, Portuguese chicken with paprika cornbread, and “Canada’s finest,” a plate highlighting the freshest in-season ingredients.