Look online. You can find discounted tickets to shows and plays in New York and other major cities, including Las Vegas and London, on goldstarevents.com, broadwaybox.com, and playbill.com, says Pauline Frommer, creator of Pauline Frommer's Travel Guides series of shopping guides.
Ask to BYO. At restaurants, see if you can bring your own wine and pay a corkage fee (anywhere from $10 and up), A good host won't flinch. "I'd thank you for choosing my restaurant first, whether you brought your own wine or not," says Richard Coraine, chief operating officer of restaurateur Danny Meyer's Union Square Hospitality Group. Also, bottled water can be marked up by as much as 300 percent, so order tap.