By now, if you haven't arranged a major summer trip, you probably won't go, and instead plan to travel in the fall. Overall, that's often a good idea -- traveling when workaday folks are otherwise tied up has some advantages. Here are my suggestions for planning that fall trip, and when to make your decisions and arrangements.
>Where to go: In the fall -- Labor Day through mid-December -- prices at most U.S. and Canadian summer-season visitor centers and attractions drop to their lowest levels of the year and crowding is less of a problem, while weather is likely to be fairly good well into October in most of the country. U.S. airfares generally don't show much seasonality.
Fall is also the slowest season of the year in the offshore beach destinations in the Bahamas, Caribbean and Mexico, so hotel and resort prices are at their lowest. And fall-season cruises, too, are usually a good deal -- if you don't mind a slightly increased risk of encountering a hurricane. Airfares to Europe usually drop precipitously in fall -- typically, they're at off-season rates by the end of August, although they may drop a bit more through September and October. Hotel rates, on the other hand, are usually up from their summer lows by August.
>Get the timing right: You can decide where you want to go anytime. But the best time to buy varies depending on what you're buying:
*Airfares: Early summer is probably a bit too early to score your best airfare deal for September through mid-December. The main current "sales" cover travel just through July. Instead, keep up with whatever sources you use to notify you of air deals, and wait to buy until you see a good promotion that includes the period when you want to travel. I don't see any major risks in waiting for an airfare sale: Fares are already about as high as the market will allow, and you can almost count on doing better with a good promotion.
*Hotels: Some good deals are already available, but major hotel chains seem to be following the airlines' lead in mounting short-fuse promotions. Currently, for example, Hyatt's promotion with AAA/AARP expires in early September, and Accor's current promotion also focuses on summer travel. As with airfares, I suggest you wait for a good promotion. As usual, however, you'll find your very best hotel prices through the flash sale websites (for really upscale spots) and through Hotwire and Priceline. On the other hand, it's never too early to book a vacation rental. Although prices can be highly seasonal, rates for the year are set and published far in advance and vacation rentals seldom run any short-term promotions. The earlier you buy the wider choice you have.
*Cruises: The fourth quarter of the year is generally the slowest in the cruise business. Even list prices are low, and the big online cruise agencies are already showing some really good rates for September through December in the Caribbean and Mexico, and you can even catch a late Alaska sailing through early September. Fall's very best cruise deals are traditionally transatlantic "positioning" cruises, usually in October: Rates already posted are as low as $40 per person per night.
*Rail Travel: Amtrak seldom runs significant promotions, so you might as well buy early to lock in the space you want. VIA Rail Canada, on the other hand, does run promotions; the best are some fantastic "Express" deals, typically covering trips up to a month in advance, so "wait for a deal" strategy seems best here. Similarly, Rail Europe and similar agencies often run promotions on railpasses, again with a fairly short purchase window.
*Insurance: If you plan to buy travel insurance, be sure to buy within a few days after you make an initial payment. That way, you can avoid hassles over "pre-existing medical conditions" and also be able to buy "cancel for any reason" coverage should you want it.