There are ways to travel to paradise even on a budget.
Accommodations: No matter what the season, ask about deals—a free night after three or four or five paid nights, kids stay free, meal credits. Condos are less expensive and bigger than hotel rooms and are perfect for families or groups of friends. If you pass up the ocean view, you'll save money. In September, October, and May, many hotels offer reduced rates.
Food: Eat a big breakfast and skip lunch. You'll probably be sightseeing or at the beach anyway. It's easy to get by with a smoothie or fruit and yogurt. If you eat lunch out, go to that high-end restaurant. Lunch will be less expensive. Early evening "happy hour" deals are a great way to save money while sampling the chef’s specialties. If you're staying in a condo, eat in or pack a picnic when you can.
Activities: Pick up free publications at the airport and at racks all over the island; many of them are filled with money-saving coupons. Activity desks—there are dozens around Kaanapali and Wailea as well as in Lahaina and Kihei—are good places to check on discounts if you're not booking in advance. However, advance booking will ensure you get the activity you want; sometimes you can save 10% or more if you book on outfitters' websites.