The great-circle (air) distance between St. John's, Newfoundland (YYT) and Lisbon, Portugal (LIS) is approximately 3,800 km (2,361 miles).
That's slightly shorter than New York–Lisbon (5,400 km) because St. John's juts far into the North Atlantic—it's North America's easternmost city. A hypothetical nonstop flight would take ~5h 30m, but no airline operates it. Connections route via Toronto, Montreal, London, or Reykjavik, making real-world travel 9–14 hours.
Historically, this stretch was a key transatlantic cable and shipping lane. The first successful transatlantic telegraph cable (1866) landed at Heart's Content, ~100 km southwest of St. John's, linking to Valentia Island, Ireland—Lisbon's telegraphic neighbor.