Best Places to See While on a Look-See Trip to Canada (Plus, Itineraries)

Embarking on a Look-See trip to Canada is a crucial step for anyone considering a move to this vast and diverse country. Such a trip allows potential expats, retirees, and digital nomads to explore various cities and towns firsthand, helping them to gauge the local lifestyle, amenities, and community vibe. It's an opportunity to envision daily life in different settings, from bustling urban centers to serene rural locales, and to make informed decisions about where to settle down.

Recommended Itineraries

For a 10-day trip, consider focusing on either the East or West Coast to maximize your time. In the East, you might start in Toronto, then visit Ottawa, Montreal, and Quebec City. On the West Coast, begin in Vancouver, followed by Victoria, Kelowna, and possibly a trip to the Rocky Mountains near Banff or Jasper. For a 20-day trip, you could explore both coasts, starting in Vancouver and working your way eastward, or vice versa, including stops in Calgary, Winnipeg, Toronto, Ottawa, Montreal, and Halifax, with potential detours to charming smaller towns like Stratford, Ontario or Wolfville, Nova Scotia.

Toronto, Ontario

Toronto is Canada's largest city and a hub for finance, technology, and culture. With a population of over 2.7 million, it offers a vibrant urban lifestyle with diverse neighborhoods, excellent public transit, and a rich array of cultural experiences. Expats and digital nomads are drawn to Toronto for its economic opportunities, multicultural communities, and extensive amenities. The cost of living is higher than in many other Canadian cities, but the quality of life and job prospects can be worth the investment.

Travel Tip: While in Toronto, don't miss the chance to visit the iconic CN Tower. For a unique dining experience with a view, book a table at the 360 Restaurant.

Ottawa, Ontario

Ottawa, the capital city of Canada, offers a blend of political significance and cultural richness. With a population of around one million, it boasts a high quality of life, numerous parks, and a relatively affordable cost of living compared to Toronto. Expats and digital nomads often appreciate the city's bilingual character and the presence of international embassies and organizations.

Travel Tip: Take a leisurely stroll through the historic ByWard Market, where you can sample local produce and artisanal goods.

Montreal, Quebec

Montreal is known for its European charm, vibrant arts scene, and bilingual populace. The city is the second-largest in Canada and offers a lower cost of living than Toronto, with a population of over 1.7 million. It's a favorite among expats and digital nomads for its dynamic festivals, culinary delights, and the blend of French and English cultures. The city is also a hub for industries like aerospace, technology, and design.

Travel Tip: Experience the city's culinary scene at Schwartz's Deli, famous for its Montreal-style smoked meat.

Vancouver, British Columbia

Vancouver is a coastal city with a backdrop of mountains and a reputation for its outdoor lifestyle. The city's population is over 630,000, and it's known for its high cost of living, particularly in real estate. However, expats and digital nomads are attracted to its mild climate, natural beauty, and opportunities in film, technology, and commerce.

Travel Tip: Visit Stanley Park and explore its lush landscapes, beaches, and the scenic seawall.

Victoria, British Columbia

Victoria, the capital of British Columbia, offers a slower pace of life with a population of around 85,000. It's known for its mild weather, historic architecture, and a strong sense of community. The cost of living is lower than in Vancouver, making it appealing for retirees and those seeking a more relaxed lifestyle.

Travel Tip: Don't miss the Royal BC Museum, where you can delve into the region's natural and human history.

Kelowna, British Columbia

Kelowna is a city in the Okanagan Valley, famed for its wineries and stunning lake views. With a population of about 130,000, it offers a blend of urban amenities and outdoor activities. The cost of living is moderate, and the area is popular among expats and digital nomads who enjoy a balance between work and leisure, with a strong focus on wellness and nature.

Travel Tip: Explore the local vineyards and enjoy a wine tasting tour at Mission Hill Family Estate, one of the region's most picturesque wineries.

Calgary, Alberta

Calgary is a city known for its energy sector, entrepreneurial spirit, and proximity to the Rocky Mountains. With a population of over 1.2 million, it offers a high standard of living and a relatively affordable cost of living compared to other major Canadian cities. Expats and digital nomads often choose Calgary for its economic opportunities and outdoor lifestyle.

Travel Tip: Visit the Calgary Tower for panoramic views of the city and the nearby mountains.

Halifax, Nova Scotia

Halifax is a historic port city on the Atlantic coast with a population of over 400,000. It's known for its maritime heritage, friendly locals, and a cost of living that's lower than in many other Canadian cities. Expats and digital nomads are drawn to its coastal charm, cultural events, and growing tech scene.

Travel Tip: Explore the Halifax Citadel National Historic Site for a glimpse into Canada's military past and stunning harbor views.

Stratford, Ontario

Stratford is a small town with a big cultural footprint, famous for its annual Stratford Festival, which celebrates theater, particularly the works of Shakespeare. With a population of around 31,000, it offers a quaint, artistic atmosphere and a lower cost of living. It's an attractive destination for those seeking a creative community and a slower pace of life.

Travel Tip: Catch a live performance at the Stratford Festival Theatre, and enjoy world-class theater in a charming setting.

Wolfville, Nova Scotia

Wolfville is a picturesque town in the Annapolis Valley, known for its wineries and Acadia University. With a population of just over 4,000, it provides a tight-knit community feel and a lower cost of living. It's a great spot for expats and digital nomads who prefer a rural setting with easy access to natural beauty and local produce.

Travel Tip: Visit the Grand-Pré National Historic Site to learn about the history and culture of the Acadians in the region.