Have you ever tried to price out and buy a series of flights to take you around the world? If you have, you probably don’t want to repeat the experience. Despite the expectation (fair or not) that we should be able to buy or book anything online without having to talk to someone, pricing out a round-the-world flight package has not changed much since I first bought one in 1993.

Indie, a new services from BootsnAll, has unveiled a leap into the present: a way to book multi-stop tickets around the world from a web interface.

I’ve known Sean Keener at BootsnAll for many years and used the site long before that. It’s been running since 1996. we teamed up (with a lot of other great travel sites) to give away a trip around the world a couple years ago, sending one lucky winner and her dad on the trip of a lifetime, geared up and exploring the planet. See who participated here. I’ve always admired Sean’s drive and bulldog intensity and when he decided to make it possible to price out and reserve a trip around the world online, I knew eventually he’d figure out a way to get it done.

Now it is done, so if a circle-the-globe flight package is in your future, go to the Indie site to check out your options. Unlike many of the trips like this you can book, theirs are refreshingly free from restrictions. You can reverse direction, put in 20 stops if you want, and travel for more than a year. There are some rules you can’t escape—like having to plan out all your departure dates in advance—but otherwise this presents a blank slate.

As I’ve discussed before on this blog, you may not need something so comprehensive, but for those who want to have the biggest expense—airfare—paid and done in advance, this Indie tool is a nice option for figuring out what it’s going to cost you. Here’s a video with more info.

If nothing else, this tool will give you a sense of whether your itinerary is batshit crazy for the amount of money you have saved or whether it’s easily doable. You can try different options and see whether trying to hit six continents in 12 months is really a smart thing to do, or whether you should prioritize. Have fun!

Want to fly around the world, but you don’t want to wing it as you go? With a round-the world ticket (or around the world ticket if you’re covering all the bases when Googling), you can set up your main airport stops in advance. When you’re ready to book it, your flight plan is set. Write one check or input your credit card once and you’re off and running for a year.

As you’ve probably noticed if you’ve done any research on this though, the prices are all over the map—because the choices are all over the map. So which routes are the cheapest? And which would cost you your whole travel savings for the year?

To get an answer to these questions, I posed them to someone I know at Airtreks, one of the best-known and longest-established companies selling round-the-world tickets. Nico Crisafulli handles public relations for the agency, so I asked him for some insider tips.

The Cheapest Round-the-World Tickets

“We do well with getting from the U.S. to Asia, Asia to Europe, U.S. to Europe (and vice versa), and locating killer combination fares throughout those continents. We find big discounts by stringing together two or three one-way tickets. We also have deals across the South Atlantic and Indian Oceans.

On their site this week, for instance, is a good RTW combo for hitting a good number of inexpensive destinations, from $2,400 to $3,000 depending on season:

New York – Hong Kong – Singapore – surface – Kuala Lumpur – Cochin / Kochi – surface – Bombay / Mumbai – Cairo – Istanbul – surface – Athens – Vienna – surface – Paris – Reykjavik – New York

There’s another that hits Munich and Rome near the end instead, for about the same price.

Here’s another route, similar price:

New York – Vancouver – Shanghai – surface – Kunming – Chiang Mai – surface – Kuala Lumpur – Cochin / Kochi – surface – Goa – Delhi – London – New York

And one more for the west coasters:

Los Angeles – Tokyo – Singapore – Kathmandu – surface – Delhi – Istanbul – London – surface – Paris – Los Angeles

Seeing a pattern here? Major world capitals and competitive big airports continually show up on the lowest-priced itineraries. See if where you want to go most is near one of those.

Shorter Routes to Consider

If you don’t have your heart set on actually circling the globe, you can often hit more destinations with a “circle the Pacific,” “circle the Atlantic” or “tour the Americas” option that makes a loop. This route, for example, can come in under $2K if you time it right:

Miami – Sao Paulo – Buenos Aires – Santiago – La Paz – Lima – Bogota – Miami

Shave it down to as low as $1,200 with this shorter route:

Miami – Guatemala City – San Jose (Costa Rica) – Lima – Bogota – Miami

This one skirting the Atlantic starts at $1,849:

New York – Bogota – Rio de Janeiro – Paris – Madrid – New York

The Most Expensive Round-the-World Tickets

First of all, the way to blow the most on these tickets is to buy them through one of the airline alliances. You’ll invariably pay more, have fewer choices, and have more restrictions. Unless you can pay for it with miles, it’s a raw deal for all but the simplest routes, and only then if you can get mileage that will bump you up to elite status. (That in itself is worth a lot.)

Otherwise, the southern hemisphere can really sock it to you. “I think the most unexpected costs are when people try to travel across the South Pacific—Australia/New Zealand to South America and vice versa—especially when stopping over in remote places such as Easter Island and Tahiti. A dearth of airlines serve those spots,” says Nico.

For this route, the price goes up to a range of $3,724 to $4,350:

Los Angeles – London – Nairobi – surface – Dar Es Salaam – Johannesburg – surface – Cape Town – Kuala Lumpur – Sydney – Nadi (Fiji) – Los Angeles

“Strangely, stopping in Hawaii on a trans-Pacific journey gets pricey, as does island hopping in Micronesia and that area.

Trans-Africa flights are notoriously expensive (i.e., flights between countries in sub-Saharan Africa). Try to do more than a few and you’ve got a major case of sticker shock. People tend also to think they can add Africa for a song, but it’s not really true. Northern Africa is better and also Kenya, but things get more complicated trying to do more than one or two African cities. Getting down to South Africa and its region will always spike a ticket price, as will Victoria Falls. We’ve actually got good prices to get to Maldives and Seychelles on Emirates though.

Also trying to hop around the USA (depending on the season, of course) makes prices jump. Keeping a U.S. itinerary to no more than three stops helps.”

Hitting every continent–a crazy idea if you only have a year anyway–will really blow the budget. Those options start at $5,344.

If you do want to get to these other regions that add on a lot, consider alternate methods to flying and look at other ideas such as package tours that bundle hotels and flights together (like from London to Morocco). Within Europe you can easily hop a train or take a budget flight booked at the last minute to add another city.

Airtreks’ RTW planning section of the site is a goldmine for anyone pondering a trip around the world. Check it out and save yourself a lot of headaches (and money).

Most people I’ve met who are backpacking around the world are adjusting reasonably well, but a fairly large segment struggles, especially in the first month or two. The ones who have it worst are the ones who leave London and land in the chaos of India with fresh shiny backpacks, ready to be scammed. It’s not fun getting ripped off badly within 24 hours of arrival.

Here are some novel things to do before you take off that will get you ready for a trip that is planned for months, a year, or more. Try these and you’ll have that worldy-wise, grizzled seen-it-all look about you from the start instead of the deer caught in headlights look.

1) Wear the same two outfits for a week. The wardrobe you have stuffed into a backpack will be limited. Get used to it.

2) Eat in the very cheapest ethnic restaurants in your city. Find the hole-in-the-wall places where you live, the ones where you see that particular ethnic group dining. If they failed a health inspection or two in the past, even better. They’ll give you a little taste of your upcoming dining experiences.

3) Eat at street stalls. Whether your city has hot dog carts, falafel stands, taco trucks, or something else, spend a few days straight eating lunch at these places. You will be getting lots of meals this way when you’re a budget backpacker on the move.

4) Spend a night in the worst motel you can find, either in your own town or when you take a road trip/weekend getaway. Odds are, this motel will still be better than many of the places you will be spending your nights, especially if it has hot water. Which brings us to…

5) Take nothing but cold showers for a week. Sure, it sucks, it’s uncomfortable, but it’s reality in much of the world if you’re on a shoestring budget. At the cheapie guesthouses level, hot water can double the price of your room. You won’t have it regularly, especially in tropical places.

6) Spend the afternoon walking around with a loaded backpack. Stuff everything you were planning on taking with you into your backpack, walk out the door, and keep going. Don’t forget that other smaller bag that will hold your gadgets, books, etc. if you’re taking one of those too. Walk for a half hour at a time, take a short break, and do it again. Stop somewhere and get something to eat, finding a place to put down that big pack and whatever else you’re carrying. If possible, come back on the public bus. There was your simulation of a day on the move.

7) Pay for everything with cash and keep track of your expenses. You will be on a budget and you will need to keep monitoring that budget to see if you’re on track.

8) Hoard your change. This exercise will feel the silliest at home, where every store always has change, but things will change in a hurry when you’re in developing countries (even Mexico), so get used to holding onto all those small bills and coins.

9) Turn off the cell phone, iPhone, or crackberry and open your senses. It pains me more than anything to see travelers staring at the little blue screen or thumbing out text messages while wonderful things are going on around them in a place they’ve never been before. (It’s also like putting a sign on their back that says, “I’m distracted. Rob me!”) Yes, I know, social media can be addictive, so break the habit now. Get some practice now experiencing, learning, and observing with no interruptions instead of cranking out more forgettable chatter. Spend a whole day having real face-to-face conversations with all gadgets turned off.

10) Navigate a new neighborhood or city. Land in a new place, bring or get a map, and spend the day finding places on foot and by bus or subway. Walk into areas that make you feel uncomfortable—though you probably want to do this in the daytime.

I doubt you can find a place with a squat toilet like you see in the photo above, but if you can get some practice on it. If not, go camping for a weekend and practice your squatting position in the woods. Work those leg muscles in the gym—you’ll be using them a lot just to go to the bathroom.

Taking a trip around the world is a big undertaking and one of the biggest chunks of the budget is going to go toward airfare. One way or another, you’ve got to at least get across the oceans before you can start traveling overland.

Ed Perkins has a rundown on different options for circling the globe in this SmarterTravel column, Finding cheap round-the-world airfares.

The thing is, they’re not really “cheap” no matter how you do it. With taxes and gotcha fees like fuel surcharges, you’re generally looking at a minimum of $2,000 for the most basic ticket in economy class, or about $5,000 for business class. That would be for something like San Francisco – London – Moscow – Beijing – Hong Kong – San Francisco. If you are trying to hit multiple continents, the price will rise. The itinerary pictured at the top from STA Travel starts at around $2,400 for students.

The least expensive option is to get it through a broker that patches together different airlines depending on which ones are cheapest for a particular leg. The hotbeds for these companies are San Francisco, Toronto, and London. I bought my first round-the-world ticket from Air Brokers and they’re still around. AirTreks is the other biggie in the U.S., with a solid reputation. Both have a trip builder function to price out itineraries and you can see example fares here. These agencies are a good bet if your itinerary is pretty set and you’re going for a year or less. They have negotiated agreements in place and commit to blocks of tickets (like the bucket shops of old) and are able to buy tickets abroad where they are less expensive.

A more pricey and less flexible option is to go with one of the airline alliances such as Star Alliance or OneWorld. You’ll pay twice as much, but you’ll be on well-known name brand airlines and you’ll usually earn frequent flier miles. If you’ve been a business road warrior for years like in Up in the Air, you might even have enough miles to cash in for a ticket.

The last option, and the one most employed by travelers on their second or third trip around the world, is to patch together flights as they go. Or to just buy the most basic RTW ticket from one of the specialist agencies and then fill in the other flights by purchasing locally in Bangkok, Delhi, Cairo, etc. There are so many budget airlines now, especially in Asia and Europe, that you can now often get most of the way around the world for cheap by just buying tickets along the way. This way you’re not locked into a specific time frame or itinerary. See this handy tool from WhichBudget.com to see who connects specific cities. Or just crack open a good guidebook to where  you’ll be.

Here’s a bit more detail from two articles I wrote a few years back for Transitions Abroad: Around the World Travel and Fly to the Clusters and Save.