The Toronto Islands -- These three islands in Lake Ontario -- Ward's, Algonquin, and Centre -- are home to a handful of residents and no cars. They're a spring and summer haven where Torontonians go to in-line skate, bicycle, boat, and picnic. However, it's also a good place to visit in winter if you're up for a bracing walk. Centre Island, the most visited, holds the children's theme park Centreville. Catch the ferry at the foot of Bay Street by Queen's Quay. You can rent bicycles on the island.
Harbourfront/Lakefront -- The landfill where the railroad yards and dock facilities once stood is now a glorious playground opening onto the lake. This is home to the Harbourfront Centre, one of the most vibrant literary, artistic, and cultural venues in Canada.
Financial District -- Toronto's major banks and insurance companies have their headquarters here, from Front Street north to Queen Street, between Yonge and York streets. Toronto's first skyscrapers rose here; fortunately, some of the older structures have been preserved. Ultramodern BCE Place incorporated the facade of an historic bank building into its design.
Entertainment District -- Also known as the Theatre District, this area, dense with big-name venues, stretches from Front Street north to Queen Street and from Bay Street west to Bathurst Street. King Street West is home to most of the important venues, including the Royal Alexandra Theatre, the Princess of Wales Theatre, and Roy Thomson Hall. Just north is the Four Seasons Centre for the Performing Arts (the new home of the Canadian Opera Company and the National Ballet of Canada), and south are the Convention Centre, the CN Tower, and the Rogers Centre.
Chinatown -- Dundas Street West from University Avenue to Spadina Avenue and north to College Street are the boundaries of Chinatown. As the Chinese community has grown, it has extended along Dundas Street and north along Spadina Avenue. Here, you'll see a fascinating mixture of old and new. Hole-in-the-wall restaurants share the sidewalks with glitzy shopping centers built with Hong Kong money.
Kensington Market -- Just west of Spadina Avenue and north of Dundas Street West is one of Toronto's most colorful neighborhoods. Successive waves of immigration -- Eastern European Jews, Portuguese, Caribbean, and more -- have left their mark. Filled with tiny but wonderful food shops, restaurants, and vintage clothing stores, it's easy to while away an afternoon here (especially on the car-free summer Sundays, when the area becomes a pedestrian-only zone).
Queen Street West -- This stretch from University Avenue to Bathurst Street offers an eclectic mix of mainstream shops, funky boutiques, secondhand bookshops, and vintage-clothing emporiums. It's also packed with eateries: bistros, cafes, and gourmet food shops line the street. Despite the intrusion of mega-retailers, many independently owned boutiques still flourish.
Art & Design District -- In the past, Queen Street West was considered edgy. Now, that description is more accurately applied to West Queen West, which starts at Bathurst Avenue and runs west to Gladstone Avenue and beyond. This neighborhood is one of the coolest in the city, full of fine art galleries; one-of-a-kind boutiques selling clothing, housewares, and antiques; and some truly great restaurants.
Ossington Avenue -- Ossington remains a hot hub of Toronto's nightlife scene with great restaurants, bars, and cafes that round out a thriving day-time culture. Combine a tour of the strip with a walk en route along Dundas Street West to see some of the hippest and newest spots the city has to offer.
Little Italy -- This charming, lively area filled with open-air cafes, trattorie, and shops, serves the longstanding Italian and Portuguese communities along College Street, between Palmerston Boulevard and Shaw Street. The crowds can't stay away, which has driven up traffic, especially on weekend evenings, and helped to expand the neighborhood offerings to include sushi spots and trendy bars and restaurants.
Old Town/St. Lawrence Market -- During the 19th century, this area, east of Yonge Street, between the Esplanade and Adelaide Street, was the focal point of the community. Today, the market's still going strong, and attractions such as the glorious St. James Cathedral continue to draw visitors. It's also an area on the rise with fine restaurants and stellar shops.
The Beaches -- Communal, youthful, safe, and comfortable -- these adjectives describe this neighborhood that's just 30 minutes from downtown at the end of the Queen Street East streetcar line. A summer resort in the mid-1800s, the Beaches' boardwalk and sandy beach ensure that it remains casual and family-oriented to this day. In 2006, there was a local poll to rename this area "The Beach" (a term preferred by many residents), but "The Beaches" is still the way the neighborhood is known.
Leslieville -- Once a down-on-its-luck stretch of Queen Street East, between Carlaw Avenue and Leslie Street, and a former industrial area, the strip has now been gentrified. There are upstart boutiques, vintage and antique stores, cafes, bars, and excellent bistros. Its borders are expanding, too -- you'll see "Leslieville" signs after you cross Broadview Avenue.
Little India -- Gerrard Street East, between Greenwood Avenue and Main Street, is well known for its festival-like atmosphere. It's partly because of the multicolored lights that light up the street at night, but the vibrant street life is visible at any time of day. The blocks are filled with Indian restaurants, grocers, and shops that specialize in saris, beautiful textiles, and treasure-chests of trinkets.
Queen's Park and the University -- Home to the Ontario Legislature and many of the colleges and buildings that make up the handsome campus of the University of Toronto, this leafy neighborhood extends from College Street to Bloor Street, between Spadina Avenue and Bay Street. Expect to find good bistros en route.
Yorkville -- Originally a village outside the city limits, this area immediately north and west of Bloor and Yonge streets became Toronto's Haight-Ashbury in the 1960s. For the past few decades, the vibe has been haute, not hippie. The pretty streets are lined with designer boutiques, galleries, cafes, and restaurants.
The Annex -- This largely residential neighborhood is a mix of small parks, handsome homes, and a strip along Bloor Street West that offers some good shopping for books and knick knacks, plus a few attractive restaurants and pubs, and one unique attraction, the Bata Shoe Museum. The Annex stretches from Bedford Road to Bathurst Street and from Harbord Street to Dupont Avenue. Revered urban-planning guru the late Jane Jacobs called this area home.
Koreatown -- The bustling blocks along Bloor Street West, between Bathurst and Christie streets, are filled with Korean restaurants; alternative-medicine practitioners, such as herbalists and acupuncturists; and shops filled with made-in-Korea merchandise.
The Danforth/The East End
Rosedale -- Meandering these quiet, tree-lined avenues offers a tour of some of Toronto's grandest homes. This residential area, composed of snaking streets that make it easy to get lost, runs from Yonge and Bloor streets northeast to Castle Frank and the Moore Park Ravine. It's named after the residence of Sheriff William Jarvis, who is largely credited with ending the 1837 Upper Canada Rebellion.
Church Street/the Gay Village -- Between Gerrard Street and Bloor Street East, along Church Street, lies the heart of Toronto's original gay and lesbian community. The "ghetto" has since evolved, and gay Torontonians now live and play all around town. Still, there remains a concentration of restaurants, cafes, and shops that offer a gay focus. Church Street is where 19th-century Toronto's grandest churches were built.
Cabbagetown -- Writer Hugh Garner described this as the largest Anglo-Saxon slum in North America, long before it became a gentrified neighborhood of restored, often pretty and pricey, Victorian and Edwardian homes. The boundaries run from east of Parliament Street to the Don Valley and between Gerrard and Bloor streets. The name is an historic reference: The original Irish immigrants who settled here in the late 1800s grew row upon row of cabbages on their front lawns. Riverdale, Toronto's only inner-city farm, is at the eastern edge of the district.
Greektown -- Across the Don Valley Viaduct, Bloor Street becomes the Danforth, which marks the beginning of Greektown. It's lined with old-style Greek tavernas and hip Mediterranean bars and restaurants that are crowded from early evening into the night. The densest wining-and-dining area starts at Broadview Avenue and runs about 8 blocks east.
Christie and St. Clair -- Until not long ago, this was a modest residential neighborhood where Torontonians would venture for some great Italian gelato or for a street party during the World Cup. Now, the area and beyond are proving a popular place to visit for good cafes, some fine Jamaican fare, and the Green Barns development, a mix of artists studios, farmers market, community gardens, and events space. The area runs west from Christie Street to Dufferin Street.
Eglinton Avenue -- The neighborhood surrounding the intersection of Yonge Street and Eglinton Avenue is jokingly known as "Young and Eligible." It's a bustling area filled with restaurants -- from neighborhood favorites to fine-dining destinations -- as well as live-music pubs and nightclubs. To the east, it intersects with the 243-hectare (600-acre) Sunnybrook park system and with the Ontario Science Centre.