To see and experience all that is Toronto, you should plan a stay of at least a week. Five days is enough to see many of the highlights: the Art Gallery of Ontario, the CN Tower, the Rogers Centre, Harbourfront, the Distillery District, Casa Loma, and plenty of the neighborhoods from Kensington Market and Chinatown to Little Italy and Yorkville. These itineraries don't include side trips to Niagara Falls or the theater festivals at Niagara-on-the-Lake and Stratford, so you'd need to adjust your plans to include them.
The four icons of modern Toronto are close enough together that they can all be visited on a single, albeit busy, day. Start at Queen and Bay streets at the eye-shape City Hall. (Its quaint predecessor, Old City Hall, is across the street.) Walk one block east to the Eaton Centre, at Yonge Street. The atrium-style roof is worth a peek even if you don't stay to browse the 300 or so shops. Next, walk back to Bay Street and head south through the Financial District, with its handsome skyscrapers; head west on Front Street to the spectacular CN Tower. It's not hard to find -- just look up. Take the speedy elevator to the observation deck and then lunch at the 360 Revolving Restaurant.
Next, pay a visit to the tower's neighbor, the spectacular Rogers Centre. (Many locals still refer to it as the SkyDome, its first moniker.) You should buy tickets ahead of time for a Toronto Blue Jays baseball game. Or, if the stadium is not in use, you can take a guided tour (call ahead). Leaving the Rogers Centre, walk or take a taxi south to Queen's Quay Terminal, part of the city's Harbourfront Centre. There's plenty to do here, from shopping and browsing the galleries to taking an impromptu pottery-making class. As the sun sets, take a stroll along the waterfront and then head to one of the great restaurants nearby. The streetcar running along the center of Queen's Quay (make sure the sign in front says Union) will take you back a couple of blocks north to Union subway station.
Prepare for a mix of culture and shopping. Spend the morning exploring the original Chinatown -- laid out west along Dundas Street behind City Hall -- all the way over to the "new" Chinatown, in and around the busy Spadina Avenue-Dundas Street intersection. Cross Spadina and turn right for the colorful Kensington Market. Settle into a restaurant along Baldwin Street or walk south on Spadina to Queen Street West (five short blocks) and make a left to check out the funky shopping district with restaurants and cafés. Spend the afternoon at the Art Gallery of Ontario (at Dundas and McCaul streets), and also see the new space-age building that hovers over the Ontario College of Art and Design, next door to the AGO. In the evening, pick your favorite ethnic cuisine and head to one of the city's excellent restaurants.
Begin the day amid the Yorkville boutiques, at the northwest corner of Yonge and Bloor Streets. Shops in restored Victorian residences, and outdoor cafés (plenty with strong Italian espresso) may charm the credit cards out of your pocket. Before the country's most chic shops settled here, Yorkville was a hippie haven in the 1960s, attracting emerging musical artists Joni Mitchell and Gordon Lightfoot. The shops spill onto Bloor Street West, and the strip between Yonge Street and Avenue Road is sometimes referred to as Toronto's Fifth Avenue. Your next stop is the nearby Royal Ontario Museum, at Bloor West and Queen's Park, with pieces from the worlds of art, archaeology, and science; even though some galleries are closed due to ongoing refurbishment, plan to spend some time here. (Across the street is the Gardiner Museum of Ceramic Art, and a short walk west on Bloor Street West is the Bata Shoe Museum at St. George Street.) In the evening, take in a play, a concert, or a comedy show at Second City.
If you're here in summer, take the subway south to Union Station and then walk to the docks at the foot of Bay Street and Queen's Quay to catch one of the ferries to the Toronto Islands; the view of the city skyline is an added plus. Make sure you know which of the many islands suits you best; in summer, particularly on weekends, kids have the run of Centre Island. In winter, take the kids to the Ontario Science Centre, with its engaging exhibits and demonstrations. The science center is 11 km (7 mi) northeast of downtown. Another far-flung spot worth a visit is the McMichael Canadian Art Collection, an outstanding museum with works by Canadian and First Nations artists, on 100 wooded acres. When you're back downtown in the evening, look for a place where you can dine alfresco -- patio dining, as the locals say -- or head to hip College Street in Little Italy.
Roam some special neighborhoods in Toronto. Purchase a TTC Day Pass, which allows unlimited use of transit vehicles after 9:30 AM weekdays (all day weekends) and is available at subway stations. Some areas to the east of downtown are Rosedale, an affluent neighborhood with antiques shops, and the Danforth, with Greek restaurants. At Church and Wellesley streets is the center of the gay community. Southeast of that is Cabbagetown, which has handsome 19th-century homes. King Street East is Toronto's new home furnishings and design district, and streetcars running east from here will take you to the Beaches, a great place to stroll the lakefront and shop. The Esplanade area at Front Street has an increasing number of trendy eateries, but St. Lawrence Market, with stalls of prepared and fresh foods, has been here forever. East of the Esplanade is the Historic Distillery area composed of art galleries, boutiques, restaurants, and home to many festivals year-round. West of downtown along Bloor Street is the artsy Annex community, and south along Spadina is the western border of the University of Toronto downtown campus. The surrounding residential area has cafés and good second-hand bookstores, particularly around Harbord Street. You'll find intriguing eateries everywhere.
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