St. John's, Newfoundland
North America's "oldest city" probably derives its name from the John Cabot expedition of 1497 — the first Europeans to explore the Newfoundland coast since the Vikings nearly 500 years before. Despite its age, the provincial capital is surprisingly youthful, a blend of college town and bustling energy center on the outer edge of North America.
What We Love
Screech: Newfoundland's homegrown rum has spawned an informal (and rum-laced) rite called a "Screech-In," during which newcomers to the island down a shot of the fire water, make a short speech, and kiss a codfish.
Quidi Vidi: Set around a lake and harbor of the same name, this waterfront neighborhood still looks (and sometimes acts) like a Newfie fishing village. Mingle with the locals at the Inn of Olde or Quidi Vidi Brewing Co.
Best Known For
Avalon Peninsula: South of St. John's, Highway 10 meanders through a long chain of seafront villages, rugged coves, and wilderness areas still a century removed from life in the capital.
Signal Hill: Topped by the Victorian-era Cabot Tower, this summit on the north side of the Narrows is where Marconi received the first trans-Atlantic wireless telegraph broadcast in 1901.
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Who It's Best For
Pub Crawlers: George Street is lined with some of the best nightlife in Atlantic Canada, with two solid blocks of pubs, bars, lounges, and music clubs.
Outdoor Addicts: From whale watching and zip lines to iceberg expeditions and hiking the East Coast Trail, Newfoundland's capital city offers a variety of alfresco adventures.
Don't Say We Didn't Warn You
Bring Layers: The climate is often dire. St John's has more wind and fog — and less sunshine — than any other major Canadian city.
You Might Go Home Empty-Handed: Don't expect to shop until you drop. Other than warm-weather clothing (like hand-knitted sweaters), there are not an awful lot of "must buy" souvenirs.
Joe Yogerst is a California-based contributor to ShermansCruise who has also written for Travel + Leisure.