Almost free: how to work & play overseas for a month the Web 2.0 way

I am currently in the middle of a month long trip around North America. Its a mix of work and play and it has cost a lot less than you would expect. Why? Because I have used a few clever strategies and a whole lot of web services and technology so that I can work and play and save money.

This post sets out how its possible to work and play overseas for a month or more without neglecting your business or spending too much.

Conferences, meetings and expos

Possibly one of the first things to consider is whether you travels can be tax deductible. In most countries you can claim a substantial portion of your travel expenses if you have a legitimate reason to be traveling. In my case I have chosen to attend two fantastic web-focused conferences, SXSW and Web 2.0, and mix in a few good meetings in between to allow me to make a reasonable claim with the tax man.

Accumulate points and use them wisely

I love loyalty reward programs, especially the American Express rewards. I use my Amex card to pay for anything I possibly can, even media bills for my agency. This enables me to accumulate a significant amount of rewards points each year, which I then use for long distance airfares. This is the best possible way to use points. Purchasing consumer goods is a bad use of points.

Airfares are usually the biggest travel expense. On this trip it could have cost a small fortune as I have flown from:

  • Sydney to Los Angeles
  • Los Angeles to Austin, Texas
  • Austin to Mexico City
  • Mexico City to Miami, Florida
  • Miami to Denver, Colorado
  • Denver to San Francisco
  • San Francisco to Los Angeles
  • Los Angeles to Sydney

That’s a lot of miles in a month and a rough retail value of well over $4000AUD. But thanks to my points I only paid a few hundred dollars. As soon as you know your airfares are free, your travel options open right up.

Book accommodation online and late

I use a few different websites to book travel. Expedia, Kayak, Webjet and more. You can use them to price flights and accommodation months before you depart in order to get a feeling for the costs in each location. However, in most cases its best to book at the last minute. Sites like Rates To Go and Last Minute sell the unsold stock for hotels around the world. The longer you wait, then cheaper it can be. The travel industry will do almost anything to shift unsold stock at the last minute.

Cultivate good contacts and friendships online

I have been fortunate to have traveled extensively over the year. Along the way I have made a lot of good friends and contacts. Likewise I have made a lot of valuable contacts and friends online via sites like Twitter & Facebook and even through this blog.

It means that many places I go I already know some locals, and knowing locals can be great. They can point you in the right direction much better than any guide book.

It can also result in very generous offers of free accommodation. On this trip I have been lucky to spent a week in Florida and 5 nights in the Colorado Rockies staying with friends for free. At an average hotel cost of $200 per night that represents a considerable saving (Approx $2400AUD). I even skied at a top resort today for free.

Naturally, I encourage all my friends to travel to Australia so I can reciprocate their hospitality. We have hosted many foreign friends in Australia over the years and will do so in the future. We’re all in this together.

Managing work from another country

Of course I can’t just take off for a month and hope everything will be OK with my business. I am fortunate to have a great team who can manage the day-to-day operations of the agency and they’re doing a fantastic job. As far as we are concerned, its business as usual. And that’s the way it should be.

But we have also set things up for me to be totally contactable and able to work. Email, Twitter and SMS are used daily for updates and questions. So far Twitter as been the primary source of communication between me and the office, my family and friends. Its fast, efficient and free.

We also use for more detailed video calls. ooVoo allows me to talk face to face with the agency, clients or family for free. All I need is some free wireless at the local cafe or library to set up a full video conference call.

My iPhone is set up with Global Roaming and data downloads but so far I have only needed it for one client call. I also have Twitter on my phone so I can be in constant contact.

I have also used Twitter for finding people and places in different cities. The day I arrived in Austin I put a message on Twitter to see if anyone wanted to meet for a beer or coffee. Ten minutes later I had made a new friend and subsequently went to several parties I hadn’t known about. Even in Mexico City I got some assistance via a Twitter contact. It has been an invaluable travel tool.

The Search function of twitter is also amazing for finding out more details of the events I have been to. Just look at the #SXSW search at to see what I mean.

My office and I also share documents online via Google Docs, allowing me to quickly read and edit without downloading or even opening an email. In fact, email has been used very little on this trip. Is that a sign of the times?

The large time difference between the US and Australia means that I can work while everyone at home is asleep, and they can conversely be working / responding while I am asleep. We have a few hours a day where we overlap for realtime conversations.

With a little strategic planning, clever use of the latest web applications and effective social networking you really can travel and work at the same time and save money doing it.

2 Responses to “Almost free: how to work & play overseas for a month the Web 2.0 way”

Great tips. The online world has definitely made it easier to do business just about anywhere as long as you have an internet connection.

The real problem is when can you get away from your business.

Comment by Jared O'Toole on March 27th, 2009

There is another site Wego Australia which is not bad for comparing flights and hotel prices.

Comment by George on January 17th, 2013

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