Planning a (Debt-Free) Dream Vacation

Most people agree that a vacation is supposed to be relaxing, but planning for one can be just the opposite. Still, poor planning can cost money and time, causing headaches and frustration when you're supposed to be getting away from it all.

Some people like to book a ticket and see where life takes them. Others prefer cruises or tours where the planning is taken care of for them. I prefer to plan my trips, researching and budgeting as much as I can while I'm at home to make the vacation as smooth as possible. If that sounds like the route for you, today I'm going to share my method, step-by-step, for budgeting and planning a vacation, including spreadsheets you download and customize.

This method is effective in planning trip logistics and budgets, laying out how to do the following:

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5 little-known websites that will save you time and money when booking airfare online

When booking airfare online, most people think of the popular online aggregation sites. You know the ones: They have the fancy commercials, catchy jingles, and washed-up celebrity pitchmen. While those sites aren't inherently bad, there are a few well-documented problems with relying solely on these larger engines:

  1. Many of the aggregation sites neglect to include smaller, budget carriers.
  2. Larger airline companies may temporarily exclude or intentionally block these aggregation sites from fares.
  3. Short-term specials or incentive sales aren't usually aggregated either. They're often only found by visiting the individual sites of the carriers.

Obviously, there isn't just one website capable of giving you the best deal every time. I wish it were that easy.

Many larger carriers make a significant amount of money off of the loyalty factor — meaning those individuals and companies who choose to fly the same airline every time for whatever reason. Because of this, they're not necessarily in a rush to make all their fare data open and available for the world to dissect. Continue reading...

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How to Earn Free Plane Tickets and Cash Back by Shopping Online

When my husband and I went to Italy in 2006, we spent $2500 on plane tickets. We're planning to spend much less for our next hop across the pond because as of this month we have over 80,000 airline miles — just enough for two tickets to Europe.

I used to think frequent flier miles were only awarded to, you know, frequent fliers. Or people who use an American Express for big company expenses. I certainly didn't think little ol' me who gets on a plane maybe once a year would be able to rack up enough miles to matter.

Then I stumbled upon Free Frequent Flyer Miles, a guide written by Gary Steiger, air-mileage earner extraordinaire. I couldn't believe there were so many ways to earn miles. Soon after, I learned about sites that offer quarterly cash rebates. From these two discoveries, my online buying process developed. Continue reading...

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How to Use Couchsurfing to See the World

What if I told you there was a different way to travel? A way to see the world outside of the hotel chains, guidebooks, and tourist traps. A way to intimately experience the real culture of everyday life. A way to connect with like-minded travelers and interact with some of the most hospitable locals you could possibly find.

Well, it's not too good to be true thanks to CouchSurfing.com. Sure, it takes some effort, a little kindness, and a dash of confidence. But let me reassure you, it's well worth it. My ultimate goal is to help take you from the "I would never do that" phase into the "huh, this might be something I should look into" phase. I hope simply to pass along just a small portion of the incredible amount of hospitality I've received from the site and the community in the last couple of months.

What exactly is Couchsurfing?
Technically, I believe it's referred to as a "hospitality exchange network". But in reality it's a social networking site, much like Facebook or Myspace, but that focuses on enabling fellow travelers to connect, meet, and even host each other. And yes, it's free.

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More about...Frugality, Travel

How to Find Great Deals on Vacation and Travel

My wife and I have begun to explore the idea of taking a trip later this year. We're in the preliminary stages of our research and budgeting. Though we aren't ready to book anything yet, it's fun to look at what's available, and to dream of where we might go.

Over the weekend, I polled my followers on Twitter to ask their advice for finding great travel deals. Here are some of the tips and websites they recommended. I'm sure I'll refer to this list often in the coming months.

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The razor’s edge: Lessons in true wealth

Our friends have a profound effect on our personal finance habits. Some friends can lead us to spending and to debt. Others offer insight into the virtues of thrift. For me, my friend Sparky has been the latter. Through his example, I learned that frugality can help me achieve my goals.

"Develop a plan that is so amazing, so glowing, that you are willing to walk blurry-eyed to work every day to make the money necessary to reach the light." — Sparky's advice to GRS readers in 2006

After my friend Sparky graduated from college, he drifted. He couldn't hold a steady job, and he didn't stay in one place for long. He traveled to Mexico. He moved to New England. He lived in various cities in Oregon and Washington.

"I don't know how you can do it," he told me once when he saw our new house. "You have a home and a wife and the same job you had five years ago. I'd hate that." He lived as a First World nomad. Continue reading...

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The Nonconformists’ Guide to Personal Finance

My short life as a daytrader

In my second year of college, I decided to take out $10,000 in student loans and become a daytrader. I could earn far more than the low 4% rate the loans came with, and I planned to finance my education with the winnings.

Sounds like a great idea, right?

There I was, hanging out in the school library, taking up two or three monitors with stock tickers running across the screen and Excel spreadsheets tracking my trades. A copy of Barron's would be spread out beside me, and the Wall Street Journal wasn't far away.

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Cheap vacation: Be a tourist in your own hometown

Last weekend, long-time GRS reader Vintek came to Portland. Kris and I joined him and his wife for a Saturday morning culinary tour. On our four-hour trek, we visited a bakery, a cooking store, and a brewery (where I drank beer for the first time — seriously). Along the way, I saw places and learned things about the city that were new to me. Afterward I realized how fun it would be to actually spend a weekend touring Portland as if I didn't know anything about it, as if I were visiting it for the first time.

With record gas prices and soaring airfares, a hometown vacation is a great option for frugal folks. Last fall, Mrs. Micah noted that hometown tourism can save money and sanity because:

  • You can save big on hotel rooms by not having any.
  • You can pack meals from home.
  • You save gas and other travel expenses.
  • You stay in your comfort zone.
  • You can use your knowledge of the area to pick cheap attractions.

But you don't have to pinch pennies if you don't want to. You'll still save money even if you stay in a nice hotel, dine in fancy restaurants, see a show, and take a couple of tours. Because you have no travel costs, and because you're familiar with the area, your vacation dollars go further in your own city. Continue reading...

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Bargain Summer Vacation Destinations

My recent series of interviews with author Tim Ferriss has given me the travel bug. I find myself plotting grand vacations (or mini-retirements). But I don't have the money to spend on a trip to London or a cruise to Alaska. My sights are set a little lower.

Fortunately, several recent articles have addressed this subject. On Sunday, The New York Times published a list of 31 places to go this summer.

"The summer of 2008 is starting out like a cruel joke, with air travel increasingly a nightmare and with wildly escalating gas prices threatening to make the road trip all but obsolete," the authors write. "The summer vacation is still an inalienable right, however. And there is no reason to forgo it this year. It will just take a bit of creativity — and perhaps the willingness to stay a little closer to home this time around — to pull it off in 2008."

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How to take a sabbatical

photos of people and places on sabbatical

In his book, The 4-Hour Workweek, Tim Ferriss proposes that we shift our focus from end-of-life "macro" retirement to more frequent mini-retirements, which might be spaced throughout a working career. Consider it a type of sabbatical, but one that you can take multiple times throughout your working life -- and not reserved for academics or the super rich.

Ferriss took time to speak with me about his notion of mini-retirements. Last week, I published the first part of the interview, in which he discussed using mini-retirements to get more out of life. In today's excerpt, he provides some real-life examples of how to put this concept in action.

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More about...Books, Retirement, Travel