When-to-book secrets for popular vacations

Through smart planning, you can ensure you get the trip you want months before you pack your suitcase. Book at the right time, and you'll get your first-choice flights, accommodations, and prices. Book late, and you may have to compromise on the details of your getaway. Knowing the best time to book can save you from a less-than-ideal experience.

If you don't believe me, listen to the hard lesson I learned about booking early. This year, I needed to buy two summer flights from San Francisco to Boston. For my Labor Day weekend trip, I booked my round-trip fare in early May for $292 (including a red-eye). I got this great price by planning months in advance. However, I didn't realize flights for all summer weekends were equally in demand, so I put off booking the second trip, which was to occur in late July or early August. When I finally went online in late June, I was shocked to find fares started at over $500 apiece.

It's ludicrous that I'm paying more to fly on a random weekend in August than I am for a holiday weekend. But that's my punishment for misreading the peak travel times and not booking early enough. Many travelers make my mistake, confident they can book their flights, hotel, or vacation package just a few weeks ahead of time. But popular travel periods sell out faster than we think.

In just one article, I can't tell you the best time to book every possible trip, but I can give some guidance on select itineraries. Here's the lowdown on the ideal times to book seven popular vacations. You might be surprised how early you really need to start planning.

Fall foliage

When the air turns nippy and trees start to swap their summer greens for brighter hues, many Americans jump in their cars to get a good look. The foliage season lasts only a few weeks in September and October, which means that hotels will be booked solid during peak times.

Early booking is essential for leaf-peeping trips during the first two weeks in October, when the confluence of the Columbus Day holiday and the brightest fall colors lead to crowds. To get the best rates and availability, book six months in advance for this peak period, suggests Erica Houskeeper of the Vermont Department of Tourism and Marketing. For other weekends, you should be fine reserving a room two to three months in advance. Procrastinators should consider bonding with nature during the week rather than weekends—in Vermont, you can get away with booking two to four weeks in advance for midweek stays.

Thanksgiving

Thanksgiving is one of the year's biggest travel times, which means you have lots of competition for airline seats. If you need to fly from Wednesday to Sunday, don't pin your hopes on a fare sale. Instead, book your trip as early as possible and leave wiggle room in your itinerary for delays and bumps.

For the most choices, book your Thanksgiving flight 45 to 90 days in advance, recommends Erin Krause, one of Expedia's travel experts. Book later and flights will be expensive and have limited availability. Book earlier, and you may find your original flight times changed as the airlines juggle their inventory.

Winter break

The winter holiday travel period may be longer than the Thanksgiving one, but it's still just as crazy. Roughly the same advice holds for flights—book as early as possible, at least 60 to 90 days in advance.

If your winter plans include a ski vacation, Molly Cuffe of Colorado Ski Country USA says the trend is to book in August, but you'll find good availability through early October. Not only will you get your pick of the best accommodations, but you can save money with package deals. If you dawdle, you'll still be able to book a ski trip, but you'll be staying farther from the slopes and many of the promotional rates will have disappeared. Spontaneous travelers should consider lesser-known ski areas, trading Vail or Aspen for one of the Colorado Gems.

Spring break

When I was a student, I didn't think about spring break until after winter break. But students who want the best trip at the most affordable rates should book no later than Thanksgiving.