Read the fine print.
Before you book, take a close look at which activities are part of the package (parasailing, waterskiing, and excursions often aren't) and whether tips and beverages (including the alcoholic kind) are extra. We've all heard "I'm staarrving!" at 10 p.m. "We always stay at resorts where food and drinks are available almost 24/7, which is nice because you don't have to think too much," says Leah Schertz of Wisconsin Rapids, WI. If you're going to Florida or the Caribbean from June through November, check for a "hurricane guarantee," a resort policy that protects your deposit if you cancel due to a storm. Know the terms: Some kick in only if the flight is canceled.
Match the kid(s) with the resort.
The larger inclusive chains, like Beaches and Club Med, have ramped up the offerings for the youngest kids lately: You'll find baby food on the buffet line and a nanny who'll come to your room. "When my kids were younger, they were crazy for the kid clubs, but now they prefer to do their own thing," says Danielle Schochet, a mom of four in Woodmere, NY, whose favorite all-inclusive is Occidental Allegro Play-acar in Playa del Carmen, Mexico. Look for after-dinner hangouts, like game rooms, to keep tweens happy. Often they're supervised; ask.
Though the airfare may be cheaper bundled in a package, you may have to transfer several times and could get whacked with penalties if you make a change. Consider paying a bit more to book it yourself. Check yapta.com or orbitz.com; both make it easy to track fares.
Get to know the staff.
Always sit at the same table at dinner and you'll probably get the same waiter. Befriend him or her. Why? Families tend to eat at the same time (early), so waiters will have lots of kids besides yours who need extra napkins. The result: a more enjoyable meal for everybody. Same goes for counselors. If your daughter clicked with the crafts leader, ask when she'll be working during your stay and plan accord-ingly. That counselor will quickly become your kid's special vacation buddy. She'll be racing to get to the kids' club each afternoon.