Choosing Your Cruise
You can find great values on cruises during shoulder seasons, which are just before and after high season. For the Caribbean and the Mexican Riviera, this is post-spring break (usually late March) through May, and late fall. For Alaska, it's May and September. If you're bound for New England or Canada, go during the window of time after the leaves have changed but before they've fallen from the trees—think late October. No matter where you're heading, the best fares are between Thanksgiving and Christmas, and just after New Year's.
Feeling brave? You can find deals during hurricane season, especially mid-August through October. Just be sure to invest in travel insurance!
Another way to save is to book a trip on a repositioning liner, when cruise lines move ships from one region to another for a new season. Routes include transatlantic crossings, when lines transfer vessels between Europe and the Caribbean, and coastal voyages, when ships travel from Alaska to the Mexican Riviera and from Canada and New England to the Bahamas and the Caribbean. There's one caveat to the great prices: These are one-way trips, so you'll embark in one city and depart in another—which means the airfare can be costly.
Beware of school-holiday periods: Presidents' Day weekend, spring break, Christmas, and New Year's are among the priciest sailings. They're also hugely popular with traveling families—and dodging other people's kids is no one's idea of a getaway.

Fall/Winter 2008 Girlfriend Getaways