TAXI! The area’s heart and soul can be found at Cumberland and Yorkville avenues.
VIBE The sound of expensive wine spilling from decanters is the soundtrack of swanky patios. Home to million-dollar condos, posh boutiques and splashy lounges.
THE CROWD The city’s well-heeled schmooze and play spot-the-celebrity.
BEST THING Roof Lounge (4 Avenue Rd., 416-924-5471) oozes with class from a bygone era. Get Joe the famed bartender to mix up a few of his world-class martinis. A narrow but necessary patio is a must-visit.
HOT ALERT With the return of Yorkville fave Sassafraz (an unfortunate fire gutted it) and a Wolfgang Puck restaurant on the way, expect long waits for reservations.
TIME HONOURED Amber may be small, but the cavernously cozy spot’s model-esque crowd doesn’t seem to mind the close quarters.
TOP PATIOS Skylounge (InterContinental Hotel, 220 Bloor St. W., 416-324-5893) has the quality of a slick Mediterranean hideaway in the sky. Fifty-one storeys up, the terrace at Panorama boasts primo views. Acrophobes can hit up Empire for a more grounded experience.
TAXI! College Street strip west of Bathurst Street to Ossington Avenue.
VIBE A blender mix of restaurants, lounges and bars. Ideal for hitting multiple spots by foot or lingering over a bottle of vintage Barolo.
THE CROWD Lounge-seeking night crawlers and couples looking to feast on some authentic Italian grub flock to the neighbourhood.
BEST THING Sneak inside one of the many buzzing lounges to catch a nightcap or groove into the wee hours with a set by some of the city’s up-and-coming DJs and bands.
HOT ALERT Sipping on a pina colada in a coconut shell at Sutra Tiki Bar (612 College St., 416-537-8755) has an authentic feel thanks to the sandy back patio complete with tiki hut.
TIME HONOURED An upscale bistro, Coco Lezzone boasts a stellar reputation thanks to bountiful seafood platters and delectable pasta. Come see why Café Diplomatico (594 College St., 416-534-4637)—just “The Dip” to regulars—has been at the heart of the scene for 39 years.
TOP PATIOS The patio at Teatro is prime real estate for surveying the beautiful people cruising the strip. This haunt gets bumping after dinner, so it’s worth staying to indulge in a long list of cocktails and martinis. (Warning: Bartenders are known to turn Coyote Ugly at around midnight.)
TAXI! Front Street, east of Yonge Street, with plenty happening on The Esplanade.
VIBE Bursts with activity during warm months, amid some of the city’s oldest structures, like the Flatiron building on Front Street or the quaint Distillery Historic District.
THE CROWD The after-work crowds whip out their corporate credit cards amongst the local new-condo set.
BEST THING Indulge in ultra-hip fare by the local celebrity chef at Jamie Kennedy Wine Bar, where the Yukon Gold fries with lemon mayonnaise are a cult hit. Sample the array of Russia’s finest liquid import at Pravda Vodka Bar (36 Wellington St. E., 416-306-2433).
HOT ALERT Head over to The Sultan’s Tent for gyrating belly dancers and tasty Moroccan food.
TIME HONOURED A quick jaunt down into the bowels of C’est What? and you’ll find live music, a long list of beer on tap and a devoted crowd of regulars. For true beer afficiandos, Esplanade Bier Markt has more than 100 international brews, perfectly paired with a succulent variety of mussels and thinly sliced frites.
TOP PATIOS The Docks takes advantage of the waterfront with a 41,000-square-foot patio, where the view of the skyline is unobstructed. In the cobblestoned Distillery Historic District, Pure Spirits Oyster House and Grill is to the city like a pearl to an oyster. Euro-style mega patios are ideal for al fresco dining.
TAXI! Southwest of Yonge and Dundas streets, the heart of downtown spreads west along Queen, Richmond and King streets.
VIBE Stiletto-clad gals and sharp-dressed guys vie to bypass the lineups at exclusive spots. The swell gives way to quaint hideaways and polished supper clubs further west.
THE CROWD Young, single urbanites in the know gravitate here to mingle at the latest “It” spot.
BEST THING Bottle service is the surest way to secure a prime spot (with a place to rest those pinched toes) in the slew of bustling über-trendy lounges.
HOT ALERT West Lounge (522 King St. W., 416-361-9004) is hard to find but worth the hunt for its super stylish decor, including faux marble walls, spread through three rooms.
TIME HONOURED At the Hard Rock Café, rock star memorabilia—like teetering platform boots worn by Paul Stanley of KISS—are worshipped. In earshot of theatres and sports venues, Kit Kat 2 (Club Lucky) (297 King St. W., 416-977-4461) is casual Southern Italian eats à go-go, while the Fox and the Fiddle offers a relaxed but lively atmosphere and a range of global beers.
TOP PATIOS The glow cast by the red-hued signs flagging Ki Modern Japanese + Bar draws passersby to the patio, where moneymen sip sake-infused concoctions amidst girls with big smiles. Slightly off the King West traffic, the sprawling patio at Brassaii is equally chic but a little less obvious.
ART & DESIGN DISTRICT
TAXI! Queen Street West from Bathurst Street to Gladstone Avenue.
VIBE Pockets of derelict buildings have undergone major reconstructive surgery to make the area a hotbed of indie art, vintage boutiques and design stores.
THE CROWD Thirty-something creative types, trendsetters and bandmates mix at a slew of casual, funky bars and lounges.
BEST THING Chances are the woman sitting next to you is carrying a worn copy of Proust in her hand-beaded purse. The good news? She’s in a band that’s gaining recognition on MySpace and is bound to entertain you after a few more pints.
HOT ALERT Skip hanging with the general population and spring for bottle service at Cheval (606 King St. W., 416-363-4933). Dark private booths offer respite from the dance floor.
TIME HONOURED Built in 1889, The Gladstone Hotel has established itself as a gathering ground for artists. Stay at one of the 37 artist-designed guest rooms or get into the groove at Melody Bar, where you can enjoy live entertainment nightly from Wednesday to Sunday.
TOP PATIOS Sky Yard at the Drake Hotel has an earthy feel with bamboo overhangs, Douglas fir tables and laid-back seating. The achingly cool pull up a stool at The Beaconsfield, which is known for its gourmet burgers and je ne c’est quoi appeal.
For more about Toronto after dark, see Nightlife That Rocks
WEB EXCLUSIVE! For more of the city’s flavour after dark, see 10 Best Cocktails.—Bonnie Malott