Let's break it down:
The Flights / Hotels
Major airlines assume that last minute flyers are business travelers. This means the airlines charge a premium for a last minute ticket because they know a business traveler will pay it because the job depends on it. Plus - airlines have cut back on a lot of routes so planes are flying full. That nonstop route will sell out leaving you with a terrible connection if you don't book early.
Exception: Travel operators like Funjet Vacations have charter flights from select cities to create nonstop routes to the Caribbean. These tour operators may discount last minute Caribbean flight and hotel packages to sell unsold seats on the charter. So if you live in Baltimore, Boston, Chicago, Dallas, Denver, Houston, Kansas City, Madison, Milwaukee, Minneapolis, San Antonio, or St Louis - a last minute Caribbean resort package may be an option for you.
In the last year, Royal Caribbean announced it would no longer be offering last minute deals. they want to train consumers that the best rates are the early rates. That has been my personal experience on both Royal Caribbean and Celebrity. I locked in a group rate for a group of three couples about a year and a half before sailing. I monitored the pricing the entire time. They ended up saving hundreds of dollars over what they would have paid if they even booked six months later. Cruise lines have realized that offering $99 last minute cruises hurts their brand. Many cruise lines are moving toward added incentives like free drinks packages, extra on board credit or free gratuities to promote sailings versus a price break. The benefit of using me to book your cruise is that I track the pricing and the promotion up until final payment to make sure you are getting the best deal.
I'm curious - What has been your experience with a last minute deal? Has it changed over time?