At first glance, it might seem like the best time to go on vacation is when you can get the best prices. Unfortunately, even if you're retired and are free to travel whenever you want, price should never be your only consideration when planning a trip. Here's why. (For more help, check out Best Places And Sites For Online Travel Deals.)

TUTORIAL: Budgeting Basics

The Off-Season
Almost every travel destination has an off-season, and it's an off-season for a reason. Usually, it's because the weather is so terrible that you won't be able to experience the main attractions. In some locations, the days are very short in the winter and there are few activities to participate in or sights to see after dark. For example, much of Europe is far enough north that during the winter it's dark by 5 PM, and the weather is often cold, windy, wet, icy and snowy.

Airfare and hotel rooms may be at their cheapest prices of the year, but tourist attractions may have reduced hours or not even be open at all in anticipation of low demand.

Off-season doesn't always occur in winter, of course. It depends on where you're traveling to. If you're traveling to India, for example, you'd probably rather avoid monsoon season, which occurs in the summer.

While savvy, experienced and adventurous travelers might enjoy a trip during the off-season, for most people, there's a better option: shoulder season.

Shoulder Season
Shoulder season is the time between the high season and the off-season when lodging and travel expenses are moderate and the weather is manageable. As with the off-season, shoulder season varies by location. It may also occur more than once a year. For example, in many European destinations, shoulder season occurs in both the spring and the early fall. In addition to saving you money, shoulder-season travel means avoiding the worst crowds. (Learn more in Shoulder Season: Your Ticket to the Perfect Vacation.)

Work Considerations
Yes, you're an adult and you can technically do whatever you want, but in any job there are better and worse times of year to take a vacation.

Don't schedule your trip during a busy period. Even if your vacation request is approved, your boss and coworkers will not appreciate your decision to leave everyone else with more work when they're already swamped. Even if you don't care about your company or anyone you work with, you need to at least look like you do if you want to have any semblance of job security.

Be present during annual reviews. Many companies evaluate all of their employees for raises and bonuses at the same time of year. If you're out of the office during this time, you might get overlooked. You want to be at work, putting in your best effort, exuding a positive attitude and getting noticed during review time. The better your performance review, the more money you'll have for that vacation.

Don't ask for time off at a new job. If you're a recent hire, you shouldn't ask to take off more than a day here and there until you've established yourself and proven that you take your work seriously. It just looks bad to take a week of vacation when you've only been in your new position for three months.

Maximize the time you do get off. Many people don't work the week between Christmas and New Year's and many employers grant some or all of these days to their employees as paid company holidays. If you tack some of your own vacation days onto either end of this period, you can take a longer vacation while using fewer vacation days. (For more, check out 5 Alternatives To Summer Travel That End Up Costing You More.)

School Schedules
If you're in school or will be traveling with school-age children, school schedules will play a major role in your trip planning. Unlike work, where there are usually several points during the year when you could comfortably be absent for a few days, school schedules are rigid. What's worse, school vacations occur more or less at the same time for everyone, meaning that traveling during school vacations can be hectic, crowded and expensive. If your only options are to travel in the summer, at Christmas and at spring break, what can you do to avoid these drawbacks?

First, even peak seasons have better and worse times. If you're headed to the beach, pick a less popular beach or a random week during the summer for your trip; don't go to a popular beach during spring break when it will be packed with raucous college students.

Second, choose strategic accommodations. If you're going to Disney World, stay in a hotel that's extremely accessible to the park so you don't waste time in the car every day. If you're going to Madrid in the summer, stay near the Puerta del Sol so you'll have more time to enjoy major attractions and spend less time on the subway.

Third, plan to maximize your time at your destination by making a detailed trip itinerary in advance and sticking to it as much as possible. This way, you won't waste time on indecision or lose sleep trying to plan each day the night before. Make reservations for restaurant meals so you can eat when you want to and avoid long waits for tables.

If school isn't a direct factor in your schedule, you'll still want to keep other people's school schedules in mind. You don't want to find yourself traveling during someone else's spring break when you could just as easily have waited a few weeks and enjoyed a more peaceful trip.

The Bottom Line
There are many factors to weigh when planning a vacation and money is just one of them. The cheapest vacation probably isn't the best vacation, and weather, work and school will usually impact your plans. You'll have to balance all of these factors and make some tradeoffs to get the most out of your trip. (To learn more about vacations, read 5 Hidden Fees To Watch For On Vacation.)

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