Wines even oenophiles haven’t heard of: Star sommelier at Jamie Kennedy Wine Bar, Jamie Drummond has an uncanny ability to sniff out fascinating (and tasty) under-the-radar bottlings. Recent offerings include a rare old-vines mourvèdre from California.

Old World: Hands down, Splendido has the best-edited sel­ection of French and Italian bottles, from $40 to $6,000.

By the glass: The 80 options at Reds Bistro & Wine Bar span esoteric to fine vintage. Even snobs will be cooing.

High-end by the glass: Where else but One can you order a single glass of 1999 Dom Perignon ($95)?

Wines you’ve never heard of: Chiado carries an extensive list of Portugal’s finest, from douros to terras do sado.

Ontario: At Treadwell Farm to Table Cuisine, James Treadwell—sommelier, and son of chef Steven—finds rare local vintages (’99 Daniel Lenko Meritage) and trophy bottlings (Le Clos Jordanne) you‘d be hard-pressed to find elsewhere.