A Rooftop Weekend in Toronto
Toronto has the potential to be an amazing destination for a summer #longweekend. It's only an hour flight from the city, has a burgeoning food scene, and there are enticing day-trip options (wine tasting, Niagra Falls). I visited Toronto in late July for the equestrian event of the Pan Am games and had a lovely time.
That said, Toronto is still a work in progress. Because it's so cold near the water during winter, the city was built inland and the waterfront was left undeveloped and industrial. The lack of any real waterfront is a shame because it can get quite hot in the summer, and it would be nice to have bars and restaurants along the water. We sought relief from the swelter in elevation--floating in the pool atop the Thompson Hotel and sipping cocktails on the rooftop of Terroni. On a hot weekend, you'll wish you knew someone with a boat. But if the weather is nice, Toronto is a lovely alternative to New York for an urban summer weekend.
Eat: Terroni (the Bar Pitti of Toronto); Sasafraz (chic brunch spot); Colette (the Lafayette of Toronto, great for breakfast); Bar Isabel; Black Hoof; Harbord Room; Grand Electric (tacos); Bar Rabal; Bang Bang (ice cream); Rock Lobster (get the Rock Lobster Caesar); Fat Pasha; El Catrin (Mexican spot with great decour); Pure Spirits Oyster House & Grill; Pulp & Press Juice.
Stay: The Thompson; The Drake.
Daytime: Explore the town on bikes using Bike Share Toronto (Toronto is quite spread out so this is your best bet to get around efficiently); visit the CN Tower and maybe even try the Edge Walk; visit the St. Lawrence Market; hang out by the pool on the roof of the Thompson Hotel.
Nighttime: Walk around the Distillery District, grabbing drinks, shopping, and eating dinner at El Catrin or Pure Spirits Oyster House & Grill); drinks at the Drake Hotel or the Chase Rooftop.
Day Trips: Niagara Falls; wine tasting at Niagara-on-the-Lake.