With literally hundreds of non-stop flights from the United States to Toronto each week—there are 300 from New York City alone—Josh will book you on an early one so you can make the most of your first day in the city. You’ll be met at the airport and transferred to Shangri-La Toronto. Spend the day exploring the designer stores and boutiques along Queen Street West, named one of the coolest streets in the world by Vogue magazine. After lunch, head to AGO, that is the Art Gallery of Ontario, where two exhibits provide insights into Canadian art. “The Idea of North: the Paintings of Lawren Harris” is curated by actor Steve Martin, while “ Into the Woods: An Icon Revisited” showcases Tom Thompson’s depiction of Algonquin Park. If, like Josh, you are a hockey fan, then you will have to pay respects to the famous figures of Canada’s national sport at the Hockey Hall of Fame, with its exhibits of uniforms and memorabilia. In the evening, Josh will send you to the Distillery District with its converted warehouses now housing retail and restaurant spaces—Josh notes that the sake tasting room is “awesome.” The Segway Ghost Tour provides a haunting perspective on this new addition to Toronto. If you would rather explore the city’s culinary scene, Josh will provide you with tips, and reservations.

On your second day you will drive east to Stratford, a little town that remade itself in the 1950s. Faced with the closure of a Canadian Pacific Railway facility, a resident launched the Stratford Festival, famous today for world class Shakespeare, musicals and new theater. This season alongside Macbeth and As You Like It, there are performances of Chorus Line and the world premiere of Bunny, a new play from one of Canada’s most exciting young playwrights, Hannah Moscovitch. Before the curtain rises, you can spend the afternoon strolling the streets of downtown Stratford which retains its small-town charms or rent a canoe and paddle along the river—yes, it’s named the Avon, just like the river through Stratford’s English namesake. Josh can provide many great restaurant options from burgers to more gourmet fare.

Today, you’ll drive southeast, along Lake Ontario to Niagara-on-the-Lake. While Niagara Falls is world famous, the town of Niagara-on-the-Lake is not quite as well known, but deserves to be. It’s been described as the prettiest town in Canada, an assessment you may agree with as you wander its streets lined with Victorian-era homes and carefully tended gardens. A 20-minute drive south to the town of St. David’s will bring you to the Ravine Vineyard Estate Winery, where you can sample outstanding wines on a beautiful estate. If you are looking to enjoy more shows after your visit to Stratford, the Shaw Festival presents ten works in four different theaters from April to October. You’ll spend the night at either the Victorian-era Prince of Wales or one of the cottages at the Olde Angel Inn, the oldest hotel in town.

A 20-minute drive from Niagara-on-the-Lake and you’ll be standing face-to-face with thunderous Niagara Falls. It’s actually two sets of falls, the American Falls and the Canadian Horseshoe Falls, and both qualify as must-see sites. You’ll get up close to the Horseshoe Falls on the Hornblower cruise, which also passes by the American Falls and the smaller Bridal Veil Falls. You can also see the Horseshoe Falls from the other side on the Journey Behind the Falls tour. If you want an unusual and spectacular perspective on the falls, Josh can also arrange for a helicopter tour of them. After you have visited the falls, you’ll return to Toronto for a night at the city’s landmark Gladstone Hotel, the city’s oldest hotel which has become a hub for Toronto’s creative scene. A few options for your last evening in Toronto include sampling the beer at the Mill Street Brewery, Japanese cuisine at Buko, or maybe late-night comfort food and drinks at the Drake Sky Yard.

On your last morning, have breakfast at Aunties & Uncles, a local favorite known for its challah and French toast, and then return home—that is, unless you have decided to extend your time exploring Ontario and Canada.