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To really see Toronto, a stay of at least one week is ideal. However, these itineraries are designed to inspire thematic tours of some of the city's best sights, whether you're in town for one day or five. We've also included a two-to-three-day escape to the Niagara region.
Start at Queen and Bay by pondering Finnish architect Viljo Revell's eye-shaped City Hall and then its regal predecessor, Old City Hall, across the street. From here, head south through the Financial District to admire the skyscrapers before swinging west on Front Street to the spectacular CN Tower. It's not hard to find—just look up. If you have more time, walk up to King and catch a streetcar east to Parliament, then walk south to the restored Victorian industrial buildings of the Historic Distillery District; choose any of the amazing restaurants here for lunch.
Begin the afternoon at the Royal Ontario Museum. If the steep entrance fee makes you wince, admire the modern Crystal gallery from outside before moving on to the Gardiner Museum of Ceramic Art, across the street, or the quirky Bata Shoe Museum at St. George Street.
Before the crowds descend at lunchtime, head for the aesthetically chaotic Spadina Avenue–Dundas Street intersection, the core of Chinatown, to browse the stalls overflowing with exotic fruits and vegetables, fragrant herbal tonics, and flashy Chinese baubles. Either pause here for a steaming plate of fried noodles, or try one of the juice bars, vegan restaurants, or empanada stands in nearby Kensington Market (head west on Dundas to Augusta and turn right). After lunch, browse the South American and Caribbean shops and groceries, modern cafés, and funky clothing boutiques. Take the College streetcar east to Coxwell Avenue (about a 30-minute ride), where the dazzling bejeweled saris and shiny bangles of the India Bazaar beckon. A fiery madras curry washed down with a mango lassi (yogurt drink) or Kingfisher beer is the perfect way to end the day.
Start early at the Toronto Zoo, where 700-plus acres of dense forests and winding creeks are home to more than 5,000 animals and 460 species. (Allow for extra time if you are reaching the zoo by public transportation, which could take over an hour.) Or venture out to the equally enthralling indoor exhibits and demonstrations of the Ontario Science Centre. If your kids are sports fans, the Hockey Hall of Fame, at Yonge and Front streets, might be just the ticket. If it’s the summer or a weekend, head to Harbourfront. There’s always kid-friendly activities and performances; watching the glass blowers in the open workshops is fascinating. In winter, rent some skates and get on the ice. Combine Harbourfront with a ride up the CN Tower to test your nerves on the glass floor that "floats" over a 1,122-foot drop and take in a view that extends far enough to let you see the mist from Niagara Falls. Head east down Queen’s Quay just past Jarvis to Against the Grain where you can toast a fun-filled day with a Shirley Temple right next to the water’s edge.
Pick up picnic supplies from St. Lawrence Market (closed Sunday and Monday), whose stalls offer a cornucopia of imported delicacies and delicious prepared foods. From here, 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 bonus. In summer, kids have the run of Centre Island. Hanlan's Point is infamous for its nude bathing, and Ward's Island has a great sandy beach and a restaurant, the Rectory Café, with a shady patio. One of the allures of Island life is the slow pace, so spend the afternoon rambling. If you'd like to cover more ground, rent a bicycle at the pier on Centre Island. Winter is not without charms—namely, cross-country skiing, snowshoeing, and skating on the frozen streams. When you're back downtown in the evening, keep the outdoorsy theme going with an alfresco dinner in the Danforth, Little Italy, or the Historic Distillery District —Toronto's only pedestrian-friendly entertainment village.
Begin the day window-shopping along the rows of restored Victorian residences on Yorkville Avenue, or reading at a sidewalk café along Cumberland Street. In the 1960s, before the country's most exclusive shops settled here, Yorkville was a hippie haven, attracting emerging Canadian musical artists like 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. The Royal Ontario Museum is worth a peek, even if just from the street, to admire the shiny crystal-inspired modern structure. In stark contrast to Yorkvillian sophistication, the grungy shops along Bloor, west of Spadina, are housed in less lovingly restored turn-of-the-20th-century storefronts. Rest your legs in either Future Bakery & Café, a student-friendly outpost for comfort food, or the more upscale, Mediterranean spot Splendido. In the evening, take in a play, a concert, or a comedy show downtown at the Second City.
If you have a few days to spare, start by succumbing to the force and brilliance of Niagara Falls. A ride on the Maid of the Mist is highly recommended, and in the afternoon—especially if you have kids—you may want to experience Clifton Hill in all its tacky, amusement-filled glory. Alternatively, head along the scenic Niagara Parkway to visit the Botanical Gardens or White Water Walk, more peaceful and natural attractions. Get dressed up for dinner at the Skylon Tower or another restaurant overlooking the falls and tuck in for a night at the slots. Admire the fireworks at 10 pm (Friday and Sunday in summer) from either your falls-view hotel room or the Table Rock Centre. The next day, a good breakfast is essential, perhaps at one of the many options in the Fallsview Casino Resort, to prepare for a day of wine tasting and strolling in bucolic Niagara-on-the-Lake. You'll need a car to follow the beautiful Niagara Parkway north to Niagara-on-the-Lake's Queen Street for shopping. Nibble and tipple the day away along the Wine Route, which follows Highway 81 as far west as Grimsby. Dinner at one of the wineries or the excellent restaurants, such as Peller Estates Winery Restaurant, then a night in one of the region's boutique hotels or luxurious B&Bs is an indulgent end to a great weekend. If you're here during the Shaw Festival (April–October), book a ticket for a play by George Bernard Shaw or one of his contemporaries.