With direct flights from more than a dozen airports in the United States, and connecting flights from the rest, it’s easy to get to Ottawa. After you arrive and get settled at your home in Ottawa, the Fairmont Château Laurier, head across the street to rent a bike and begin exploring the city on two wheels. You can pedal along the 126 mile-long Rideau Canal—but don’t feel like you need to ride its entire length. In the winter the canal becomes the world’s largest skating rink when temperatures drop low enough, but in the summer the sunny pathways along its banks are popular with cyclists as well as joggers and pedestrians. Make a detour to Nepean Point for its stunning panoramic views over the Ottawa River, before locking up your bike and seeing the remarkable collection at the National Gallery of Canada. Having sated your senses, please your palate with dinner in Ottawa’s vibrant Little Italy neighborhood, concentrated on Preston Street. Pub Italia is a local favorite combining the best of a trattoria and a craft beer pub, with an extensive "Beer Bible" that includes brews from around the world. After dinner, go to Parliament Hill to see the Northern Lights sound and light show, a free dazzling spectacle celebrating Canada’s history and vision for its future (July-September).

Start your morning soaring above Ottawa in a vintage 1939 open cockpit plane with Ottawa Biplane Adventures at the Canadian Aviation and Space Museum—aviator goggles included. You’ll get a bird’s-eye perspective on the city, before you descend and return to Parliament Hill for a free guided tour to learn about the nation’s history as it prepares to celebrate its 150th anniversary in 2017. The current buildings of Centre Block, constructed in a grand Gothic style, date from 1916, after the earlier parliament was destroyed by fire. In the summer, guided tours are also offered of the older historic buildings of East Block, completed in 1866 and restored to their appearance in 1872. Head next to the ByWard Market neighborhood where dozens of restaurants serve whatever cuisine you might be in the mood for—from Indian to Irish, Malaysian to Mexican. Cari will provide you with personalized recommendations. After lunch, continue to the Canadian Museum of History, the country’s most visited museum. The engaging exhibits here cover the epic tale of Canada with its French and English explorers; First Nations, Inuit, and Métis cultures; fur trappers and trading posts; and the development of western Canada. Next, fast forward to Ottawa’s current culinary scene—depending on your interests, Cari will direct you to Union 613 for Southern fare, SIDEDOOR for its Mexican- and Asian-inspired dishes, and Whalesbone for seafood, or many other top restaurants.

Begin the day by exploring Gatineau Park. Located just 15 minutes from downtown Ottawa, over the border in neighboring Québec, this 139-square-mile park offers a chance to experience a slice of Canadian wilderness on more than 100 miles of walking trails. Have lunch at the tearoom at the Estate of Prime Minister Mackenzie King, a dominant figure in Canadian life in the 1920s to 1940s, located within the park. Back in Ottawa you’ll pick up a rental car and head south to one of Ontario’s wine regions, Prince Edward County. Drive south from Ottawa to historic Kingston to admire its grand 19th-century limestone buildings. Take a scenic drive on the Loyalist Parkway along the shores of the St. Lawrence River for part of your journey to The County. Your hotel for the next two nights will be one of Cari’s favorites in the region, the 13-room Drake Devonshire, located in a lakefront former foundry in Wellington.

In a short period, Prince Edward County has emerged as one of Ontario's most exciting destinations with its award-winning wines and new hotels. Growing in popularity, the area’s rolling countryside, beautiful beaches, and countless lake views are best explored on two wheels. After you have built up an appetite, stop at the Wellington Bakery to refuel. In the afternoon, Cari will arrange for visits to some of the area’s leading wineries, including Norman Hardie, the Grange, and Long Dog. You’ll end this bucolic day, paired with glasses of the area's celebrated pinot noirs and chardonnays, at the East & Main Bistro which serves the best of local, seasonal produce in creative and always delicious dishes.

While Cari is reluctant to pick a favorite town on the island, she admits to having a particular fondness for Bloomfield. A thriving community since the 19th century, its streets are lined with Victorian buildings lovingly restored and today home to boutiques and antique stores. When you are ready for lunch, Cari recommends the Agrarian Bistro & Bar and The Hubb, at Angeline’s Inn. Don’t order dessert and instead end your trip to Ontario on a sweet note with scoop at Slickers Ice Cream, an old-fashioned (and cash only) ice-cream parlor on Bloomfield’s Main Street. You’ll then return home via Toronto, a two-hour drive along the shores of Lake Ontario or, even better, ask Cari to extend your explorations of Canada.