Passenger air travel must have one of the most complicated, opaque pricing systems known to man. The price of a ticket depends on date of travel, date of booking, time of arrival, time of departure, one-way or roundtrip, how many seats are left, the price of oil, and who knows what else. I mean, this is an industry that overbooks on purpose because they gamble on how many people will miss their flight, and will start to charge for restroom access by the second any day now.

Sites like Travelocity and Expedia have made buying your own airfare much more simple, but if you’ve every tried to make a complicated booking with an extended layover, open jaw, multiple cities, or international transfers it’s still quite a maze. In the old days you’d ask a travel agent and hope they were good, but now you can ask the crowd at Flightfox.com. Thanks to reader Mike for the tip.

Simply enter your trip details and offer a bounty ($19 minimum) for the best flight booking in your own opinion. In addition to a low price, you may prefer a certain airline, have a lot of baggage, require no stopovers, or be willing to endure extra stopovers if it saves money. Ideally you’d choose the best option, pay the bounty, and walk away with a better result than you’d have gotten otherwise. If you don’t like any of the options, you owe nothing.

If you’re already a savvy frequent flier, then you can sign up and earn money as a Flight Expert deal finder. Flightfox takes 25% of the fee and you keep 75%. According to Techcrunch, about 5-10% are indeed moonlighting travel agents, and the rest are just well-versed travelers.

I definitely plan on trying this the next time I have a multi-city trip. Anyone use it yet?

Update: About to fly? Get 25% off Flightfox with this link!

I just got back from my trip to Orlando, where I tried the new car rental website AutoSlash.com to book, and previously wrote an introductory summary of their features. To briefly recap, the website takes advantage of a unique feature of car rental reservations to continuously check for lower prices over time and re-book you whenever there is a price drop.

Here is the price history of my one week rental of a mid-size car in April 2011 from Orlando International Airport (MCO). I later realized it included Good Friday and Easter weekend, which I think increased the demand of cars.

• Day 1 – $665.61 including all taxes and fees, with Payless. This was really the lowest price I could find at the time across Kayak, Expedia, etc.
• Day 2 – $346.18 with Dollar Rent A Car at .
• Day 3 – $320.41 again with Dollar.
• Day 38 – $273.68, final price with Dollar.

As you can see, there was a flurry of activity in the beginning, nothing for a long time, and then finally one last price drop at the end. This is only a theory, but I think that the folks behind Autoslash do a price search for a week or so after your rental reservation is first made, and again a week or so before your actual rental date. Or perhaps this is just a result of how the rental agencies vary their prices over time.

Regardless, I was really happy with my experience, and will use them again in the future. They found a better price than I could have found, with really zero effort on my part. Many of these rental agencies are clones of each other anyway. I picked up my car from Dollar with no issues with my special coupon code, and drove away in a huge Ford Crown Victoria with 9 miles on the odometer since that’s all they had left. I declined all additional insurance coverages from them, and returned it with no problems. This last part is more of a testament to that specific Dollar franchise, but it increases my confidence with places that aren’t Avis or Hertz.

The following is a guest post from reader Chris, who shares a quick and dirty (and cost-conscious) examination of Round-the-World Travel. He writes about about making a life of long-term travel and other related topics at ChrisCarruth.com.

$10,000 goes a long way. That’s a healthy drop in the retirement bucket, a sizable boost to any portfolio, a new(er) car or, as I’m about to advocate, an adventure of spirit and culture and affirmation that most never embark upon.

Would you believe me if I told you that you could travel the world for $10,000? Hopefully, by the end of reading this you’ll see the opportunity for what it is. Of course we aren’t talking about stopping at the nearly 250 UN recognized nations, but rather circumnavigating the globe while stopping at a selection of countries and cities. Your time frame, your itinerary, your budget (and your sensibilities) will set the limits of your travels, so keep them in mind at all times.

Being readers of MyMoneyBlog.com, I think it’s safe to assume that you’re all fairly versed in saving methodologies and tips and tricks and are in, at least, a decent financial state. If you’re a new reader or simply don’t have that kind of scratch lying around, I didn’t leave you out. I’ve left some time honored travelers tips at the bottom to both save money for your travels and to pinch pennies while on the road. General rules of this study:

• I am traveling solo.
• I have gear and vaccinations.
• I have $10,000.
• I will travel for 3 months – 1 week in the US. 5 weeks in Europe and 6 weeks in Asia.

Consideration #1 – Airfare

Costs: $1,700
Remaining budget: $8,300

Airfare these days is not only the most economical choice, but also the least logistically imposing method of traversing the globe. There are two main schools of thought when it comes to RTW airfare – have it your way or go prepackaged. Customized itineraries allow for greater flexibility of schedule, freedom of destination and directional independence, while “pre-packaged” RTW tickets typically want you flying East-to-West (or vice-verse, no hopping back and forth), have a handful of stops and must be used within a certain date (usually within one year from purchase).

My focus on traveling will be South East Asia and Western Europe in a west-to-east route. I’ve opted for an itinerary from Boots’n’all Travel, who partners with the Airtreks to bring all this in at $1299 (as of September 2010, see current RTW specials here) . There are always some hidden fees, so let’s buffer that up to a straight $1500.

Flight itinerary – SE Asia & Europe Budget Ticket: San Francisco or Los Angeles – Manila – Borneo (Kota Kinabalu) – Singapore – Angkor Wat (Siem Reap) – surface – Saigon (Ho Chi Minh City – Bangkok – surface – Kuala Lumpur – London – Amsterdam – surface – Paris – San Francisco or Los Angeles from US$1299

Note: This sample itinerary is good through September 30th. Each month Boots’n’all offers different routes, but the prices, and locations, generally stay the same.

In the interest of creating as realistic a scenario as is reasonable, I’ll dish up the fact that I don’t live in San Fran or L.A. I’m a Colorado Springs resident…a quick check on Kayak.com shows that round-trip airfare from my home to the Bay Area and back runs less than $200. Done (and subtracted from our budget).

On a side note, if you’re concerned about the environment impacts of air-travel, you’ll be happy that the sustainability movement has more than a foothold in our modern travel climate. Carbon offsetting is an option as are bio-fueled jets (not commonly available…). Of course, these will up your costs and for the sake of staying under budget I’ve left them out.

Consideration #2 – Lodging

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This is a interview/guest post with blog reader Ariel Hoffman, who recently spent a year traveling around Asia with his girlfriend Michal with a combined budget of only $10,000 – and managed to come back with $3,500 of it! I love to read nonfiction travel essays, so not only are there some great frugal travel tips below, it was also very exciting to read about their adventures. Thanks again for sharing, Ariel!

What was your inspiration to go on this adventure?
In Israel, it is mandatory to serve in the armed forces for at least 3 years. After that you just want to get away, and Asia is the perfect destination for someone who’s just saved up 3 years worth of the army’s 100$-a-month salary. Also, Israel’s a pretty small country, so there isn’t much domestic travel to be had like there is in the US.

The itinerary my girlfriend (Michal) and I came up with was mostly about avoiding the rainy season, and minimizing air travel. Air travel is expensive and boring, and you try to avoid it if you have a lot of time to spend.

How did you come up with your budget? Did it end up costing more or less than you thought?
We sat down and did some serious homework, mostly on websites like lonelyplanet.com and their forums. The budget they offered sounded ridiculously low, so we nearly doubled everything we read about, and came up with a rough estimate of about 10,000$ for the two of us, for the entire year.

What we realized, however, is that not only were the estimates online pretty accurate, but also that two people don’t spend exactly twice as much as one – lots of things are shared (such as meals, transportation, hotel rooms etc.) and so it’s more like budgeting for a person and a half rather than two.
We were very pleasantly surprised when we came back home to count our remaining traveler’s cheques and see we still have about 3,500$ left over for next time!

How did you fund it? Did you save up the cash upfront, borrow some money, work while on the trip, or some other combination?
In preparation for our trip, we both took on extra work and saved up every Shekel we made. It took us about 5 months. Once we reached our goal of 10,000$, we exchanged all our cash into traveler’s cheques – a great way to keep your money both liquid and safe when abroad. Luckily for us, the exchange rates were in our favor the whole time, which gave our savings an extra 2%-5% throughout the journey.

Walk us through a typical day on your Year in Asia trip.
Most days would begin with trying to find breakfast – not always an easy task. Most Asian countries do not serve what we would consider breakfast, especially my vegetarian Michal. Although chicken porridge and spicy rice is very nice, it’s not everyone’s idea of the right way to start your day. After eating some novel type of cookie in spiced tea, we would set off to whatever National Monument/UNESCO World Heritage Site/Giant Temple/Yearly Festival was in the town on that day. After a day’s tour of the attraction we would start hunting for a suitable lunch, which meant looking around for a street stall with a good crowd, or a local restaurant with a queue. Nothing says fresh like a long line of customers, and Asian vendors normally close their stalls every day when they’ve exhausted all their stock, so food is never kept overnight and doesn’t have time to spoil. Another plus is that the food is not made of pre-cut ingredients, which makes preparation slower, but at least you see exactly what you’re getting so there are no surprises.

Evening was normally a time for sitting on the beach, going to some performance or sitting in some tea-shop with friends. For a while we had a small kitchen in our room, so I would cook dinner for us while Michal practiced yoga. In China we bought a Wii, and at night we’d plug it in and invite friends over for kart racing – it’s OK to enjoy modern fun even when on the road!
We spent a lot of time on trains and buses, getting from A to B. Sometimes as long as 27 hours! Israel’s longest train ride is only 4 hours long.

What are some basic money-saving tips you might offer us readers?
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