Video More Video

NEW YORK (CNN/Money) - Are you having a manic Monday?

Maybe you scraped off your windshield and rushed off to work, only to find your desk buried in paperwork and your boss breathing down your neck.

A two-week vacation hardly seems time enough to recuperate or to take that special trip you've always dreamed of. What would it take to enjoy a month, three-month or even six-month furlough from work? These Five Tips tells you how to plan that extended vacation.

Before you imagine life in the Greek Islands, think about the reality here. Dee Lee, financial educator and author of "Women and Money," says the idea of taking six months off from work "is a very scary proposition for some people."

"If you're seriously thinking about it, it will take you a year to a year and a half to plan it right," she said.

According to Lee, you will need: Six-months of living expenses to cover your usual financial responsibilities, money to cover travel or other expenses during the sabbatical, and another three months living expenses just in case you need to look for a new job after you return.

This will all have to come from your savings since your boss is not likely to keep you on the payroll, if he's even nice enough to hold your job.

To see if you have the savings built up to take time off, calculate the bottom line. While you can exclude some work expenses, such as commuting and dry-cleaning, without a paycheck you will have pick up the tab on your health care. Lee says that can cost between $400-$500 per month.

Doug Flynn, a certified financial planner, warns against other hidden costs.

"If you're at home, writing a book, remember your utilities are going to be higher," Flynn noted. "You'll likely have you're A/C or heat on all day when you used to have it off while at work."

You might also consider ways to make income while you're off, like renting out your house while you travel. To ensure you are thinking of everything, it's a good idea to talk it over with your financial planner. If you don't have one, hire one by the hour. For a list of financial planners in your area, log onto www.GarrettPlanningNetwork.com.

Extended leaves are not that unusual. According to the Society for Human Resource Management, one in five companies surveyed say they offer employees a sabbatical program.

Arranging for a leave of absence is usually better than straight-up quitting. After all, the idea behind a sabbatical is to ask your boss if you can take some time off with the intention of returning to your job.

"You have to have a lot of confidence to ask your boss for a sabbatical -- and a really good skill that will still be worth something to your boss in six months when you return," Lee said.

Evaluate your importance at the company. If you're a long-term asset, your employer may be okay with some unpaid short-term leave.

Also ask your Human Resources representative exactly what your company's sabbatical program offers. Besides pay, you'll also want to know what happens to your benefits. Will you lose your health insurance? Can your boss eliminate your job while you're gone? Can you get COBRA medical insurance coverage through your employer? COBRA is a federal law that requires many employers to allow employees who leave a firm to continue group health coverage provided they pick up the cost of premiums, anywhere from $400 to $500 a month.

When you go before the big boss, be honest about your real plans. Not sure what to say? Lee suggests your proposition sound like this: "I'm burned out. I'm willing to take a six-month absence without pay and pay for COBRA coverage in the meantime. I need to rejuvenate to become a more productive employee. So I am planning some travel in Eastern Europe. But I'd like to ensure I can return to work full-time when I come back."

Lee also suggests tying up lose ends for your boss by finding a temporary replacement.

It's highly unlikely that you'll receive a paycheck during your sabbatical, so you won't be able to contribute to your 401(k). That will a gap in your retirement planning.

You can minimize the damage however, by timing your sabbatical well, according to Flynn.

"Talk to your Human Resources department, ask what happens if you don't contribute," Flynn advises.

Many plans have rules about re-starting contributions to your 401(k) after quitting them.

"Some will make you wait a year to restart, and some have enrollment periods. So if you leave on sabbatical in January and come back in July, you might have to wait a year and then wait until the next enrollment period," he said. "With a sabbatical in all that, you could miss contributing to your 401(k) for as long as two years."

Deciding to take a sabbatical really is a personal decision, unless you're married. If one of you decides to take time off of work, it's important to think of the ramifications on the other spouse and your joint finances.

Lee says you really can't decide to go on a sabbatical when you're married, unless your spouse is willing to come onboard financially. If you lose your health benefits, can your husband put you on his? With only one income, can you even afford your usual standard of living?

If you're planning to travel during your sabbatical, you need to set up your home or apartment before you go. If you rent, consider a sublet, if your lease allows it. Log onto www.CraigsList.org to connect with people looking for short-term rentals in your area.

If you own home, consider renting it out for some extra income. Susan Godfrey, a Milwaukee-based realtor, suggests you talk to a real estate agent to help you put your house on the rental market. To find an agent in your neighborhood, check out the National Association of Realtors Web site at www.Realtor.com.

Your agent can help you calculate a monthly rent for your home and refer you to a real estate attorney to help draw up a lease. Be sure to incorporate rules into the lease about what tenants can and cannot do in the house.

Godfrey also advises you to ask for a damage deposit and take photos of the house in case you return to a banged-up home. And make sure someone else is watching over your home while you're gone. Your real estate company can refer you a concierge service or a professional management company to act as a landlord.

A friend may be even more diligent, according to Godfrey, but be sure to leave them with a list of clear directions and contacts for your handyman, and plumber.

Gerri Willis is a personal finance editor for CNN Business News and the host for Open House. E-mail comments to 5tips@cnn.com.