A Perfect Toronto Weekend Getaway

People watch the sun set over the Toronto skyline from a tour boat

Canada’s largest city, Toronto is the country’s commercial and cultural center. It’s a big, bold and vibrant city of diverse neighborhoods and inspiring museums and art galleries. Jane Jacobs, the famous chronicler of America’s cities who moved to Toronto later in her life, described the appeal of Toronto as coming from it having “a remarkable quality for a city of North America—it’s alive.” Michael Holtz of SmartFlyer is another American who has fallen for the charms—and exciting atmosphere and attitude—of Toronto and his three-day itinerary includes some of his favorite stops.

A woman stands in the door of a shop


Toronto's Many Neighborhoods

The big city of Toronto is made up of many smaller villages. Whether you are interested in the galleries of Queen Street West, the restaurants in trendy Ossington Village, or shopping for vintage finds in Leslieville, Michael will share the addresses of some of his favorite places. If you want to get to know the architecture, history and life of the city in more depth, he can also arrange private guided tours.
Michael Holtz


Michael Holtz

Michael Holtz is the ultimate jet-setter and the original Smart Flyer. He founded SmartFlyer over 20 years ago after graduating from Washington University in St. Louis and he has been traveling everywhere ever since. His curiousity sends him around the globe in search of the best that the world has to offer. Michael is widely known for designing unique, once-in-a-lifetime itineraries and always knows the smartest way to issue First/Business class tickets for his discerning clients. Michael sits on both the Starwood and Park Hyatt Advisory Boards.
A crowd gathers around a pool at night. Large glowing letters spell out the word Toronto in rainbow colors. A pair of twin skyscrapers are lit by red lights

DAY 1Toronto: Art and Music

Served by quick flights from many US gateways—it’s 90 minutes from New York and Chicago—you can make the most of your first day with an early arrival and no jet lag to slow you down. After a quick stop at your hotel, continue on to the first of your cultural stops, the Art Gallery of Ontario. At over 480,000 square feet, it’s one of the largest art galleries on the continent. Its renovation is also a showpiece of architect Frank Gehry, a Toronto native. Afterwards, head to Bloor-Yorkville, a neighborhood of unique boutiques and high-end stores, especially along the strip of Bloor Street nicknamed “the Mink Mile.” In the summer the air is filled with music in Toronto, with a crowded calendar of festivals. Schedule your trip to coincide with one of them and Michael can arrange for tickets to an open-air concert at Luminato (June 10 to 26), Way Home (July 24 to 26), Veld Music Festival (July 30 and 31) or one of the city’s many other cultural events.
A row of people in red jumpsuits lean off the top of the CN tower. They are secured by a rope and harness. The lake can be seen in the distance.

DAY 2A Walk on the Edge

Start the morning with coffee and breakfast at the popular Thor Espresso Bar before getting the lay of the land at one of Toronto’s most famous landmarks, the CN Tower, which rises 553 meters (1814 feet above the city). From its observation deck you’ll be able to see all of Toronto, and beyond. If you are feeling especially daring, you can strap on a safety harness, step outside and walk along the perimeter of the observation deck on the Edge Walk. Next, head to the historic St. Lawrence Market to browse the produce, artisanal food products and snack on local fare before continuing on to one of Michael’s favorite stops in Toronto, the Distillery District. There you can shop the stores of the pedestrian-only village and enjoy a glass of Gooderham & Worts whisky. This afternoon visit another of Toronto’s cultural highlights, with a design by another leading starchitect. The Royal Ontario Museum has more than 40 galleries containing thousands of works of art and cultural artifacts and a striking 2008 addition designed by Daniel Libeskind. After you are sated on culture get ready for a night exploring one of Toronto’s livelier neighborhoods, like Queen Street West or Ossington Village for French fare at Boehmer, a beer at Bellwoods Brewery, and burlesque at The Ballet.
A tall tower seen behind a port points into the sky. People walk along the water.


DAY 3Baseball and Urban Exploring

Spend your last day in Toronto enjoying that quintessential summer experience, a day at Rogers Centre to see the Toronto Blue Jays, the nation’s sports team, play. Michael will arrange for box seats and you’ll be able to cheer on the team that made it to the playoffs in 2015 and, as any local fan will tell you, are ready to go all the way to the World Series this year. Alternatively, you can explore some of the different neighborhoods of what is one of the world’s most diverse cities with over 140 languages spoken here and half its population born outside Canada. You won’t be able to experience all of them in a day but you can at least visit a few neighborhoods—and save others for your next visit to Toronto. Start your morning in the historic Chinatown (though it’s actually one of six Chinese communities in the city). Hundreds of restaurants and stores along Dundas Street West and Spadina Avenue serve the community and curious visitors. Afterwards you can hop on one of Toronto’s streetcars en route to Palmerston/Little Italy—the city has the largest streetcar system in the Western Hemisphere. Whether you end your visit at a trattoria in Palmerston or enjoying a plate of steaming noodles or a spicy curry at a restaurant in another Toronto neighborhood, you may find yourself planning your next visit before you have even started the journey home. After one taste of big, vibrant Toronto, you’ll want to come back for more.
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