SWANKY SPOT One Restaurant is the place to see and be seen, where businessmen and ladies-who-lunch sit Botoxed cheek by lifted jowl. High ceilings, slate-black, chocolate-brown and sexy splashes of red create dramatic spaces to lounge and dine on luxe dishes like foie gras with cherries, butter-braised lobster and Wagyu rib-eye. 116 Yorkville Ave., 416-961-9600.
WINE & WEDGE The impressive wine list and cheese menu—offering almost 30 cheeses—will bring you into Carens Wine and Cheese Bar, but it will be the secluded back patio that keeps you whiling away a soft autumn night under a leafy canopy and the dappled light of Moroccan lanterns. 158 Cumberland St., 416-962-5158.
CASUAL BREW For almost 30 years, the heated rooftop patio at Hemingway’s has been the place to take a break from the nabe’s highfalutin ways with a pint and some pub-grub. Bonus: it’s a perfect perch to watch the beautiful people misbehave on the patio below at Amber. 142 Cumberland St., 416-968-2828.
CHIC BISTRO This art nouveau stunner will transport you to Paris. At Michelle’s Brasserie, an outstanding wine and beer list complements brasserie classics: French onion soup, beef Bourguignon, steak frites, cassoulet. A thoughtful touch is the soft red throws waiting on patio chairs to drape over chilly shoulders on cool fall nights. Renaissance Courtyard, 162 Cumberland St., 416-944-1504.
MANGIA! A few steps beneath the shops of Yorkville Avenue, enter a world of tradition at Bellini’s Ristorante, with dark-wood wainscoting, ochre walls and tapestry-covered chairs. Classic Northern Italian dishes dominate—lobster ravioli, truffle risotto, Provimi veal osso bucco—but some, like scallops with yuzu, show a touch of fusion flair. 101 Yorkville Ave., 416-929-9111.
FRUITFULLY FRENCH Tucked away off Yorkville Avenue, enjoy the quaint charms of Le Trou Normand—antique china in farmhouse hutches, worn Persian rugs over crazed tile floors. Its French bistro menu highlights steak au poivre, duck à l’orange, moules marinière and more. And the name? It refers to a traditional palate-cleansing shot of apple brandy between courses. 90 Yorkville Ave., 416-967-5956.
LUXE LANDMARK Airy, cream-coloured dining rooms flow into satiny, celadon-tone lounges at Sassafraz. Skylights flood the space with natural light, while a waterfall soothes. Champagne pairs perfectly with a menu of modern riffs on Mediterranean and French: foie gras with daikon and persimmon, and sweet pea risotto with butter-poached lobster. 100 Cumberland St., 416-964-2222.
MED CLASSICS At its pretty little Victorian home, Trattoria Nervosa features unpretentious Southern Italian fare with a long list of authentic antipasti, pizzas and pastas. Value, quality and a relaxed atmosphere bring a welcome touch to this chi-chi ‘hood. 75 Yorkville Ave., 416-961-4642.
MYTHIC MENU At Pangaea, you’ll find sanctuary from the crowds and a modern aesthetic. The menu focuses on both local sources—Nunavut caribou, truffled gnocchi with Nova Scotia Lobster—and luxury, with hard-to-find jamón Ibérico de bellota, a Spanish cured ham. The cellar is a Wine Spectator magazine Award of Excellence repeat winner. 1221 Bay St., 416-920-2323.
TIP! Jump on the Bloor-Danforth subway line and get off at Bay station. The east exit brings you to Bay Street, from which Cumberland Street is just a few steps north. The Bellair Street exit puts you across the street from The Village of Yorkville Park, south of Cumberland.