The first thing I would do after waking up is take my wife, Nina, to the Park Hyatt (4 Avenue Rd., 416-925-1234), where we would check into the Algonquin Suite ($5,000). I hear it has incredible views, a wet bar and a shower for two. We’d go to the hotel’s Stillwater Spa, where we would get the couples massage ($365). For lunch, we’d hit the Studio Café (21 Avenue Rd., 416-964-0411) for what I consider the best burger in town: Canadian cheddar, caramelized onions, mushrooms, bacon and fries, plus a bottle of Perrier (lunch for two, $58). I have cravings for that burger even when we’re in Italy. Afterward, we’d visit Joel Carman at Over the Rainbow (101 Yorkville Ave., 416-967-7448), because there’s no one else who knows how to make an ass look as good in jeans. I’d buy a pair of Earnest Sewn ($250) and Nina would get a pair of Paige jeans ($265). I’d stop in at the Maserati showroom (101 Avenue Rd., 416-962-5325) and splurge on a Gransport coupe ($137,000). My first stop in my new wheels would be the Puma store (2532 Yonge St., 416-486-7862), where I’d pick up 11 authentic replica World Cup Italy jerseys ($1,199) for me and my 10 buddies, who would be waiting for me at the Astra Sportsplex (2839 Rutherford Rd., 905-303-0552) to play a round of indoor soccer ($125). Dinner would be at Morton’s (4 Avenue Rd., 416-925‑0648). Nina and I would invite my parents, Josie and Mimmo, and my brother Sal and his wife, Nancy. Everyone would order salads and steaks—I like the chopped salad and Cajun steak—except my mom, who would probably have something lighter, like crab cakes. We’d share two bottles of ’97 Tignanello (dinner for six, $925). But we’d have to eat quickly to make it to our platinum seats at a Toronto vs. Montreal hockey game at the ACC (40 Bay St., 416-815‑5500, $2,290). The men in my family are big Habs fans, but we’ve never all gone together; plus, I don’t think my mom has ever been to a game. Afterwards, Nina and I would return to our suite, where I’d whip up a dinner of spaghetti and Nutella crêpes. Before bed, we’d open a bottle of Moët & Chandon ($135) and watch Lina Wertmüller’s Ciao, Professore! (Bay Street Video, 1172 Bay St., 416-964-9088, $3.75).

$147,615.75