Planning 2 Months in South America and How I Outsourced it Productivity / Travel

Recently, we decided that we’re ready to get out of the rainy season here in Costa Rica, which is usually fine in the mornings, but very rainy, foggy, and cold in the afternoons – at least up in the mountains where we live. So, we’re going to be spending September and October in South America this year, followed by a couple weeks in the States to visit family (and go to Disney World – yay!). We’ll come back to Costa Rica mid-November. As you can guess, we’re pretty excited about the whole thing.

Hiring a Personal Assistant

However, since September is less than two weeks away, this doesn’t give us a lot of time to plan the trip. And with how I tend to plan (ie. way too much web research), I knew I’d need some help. So I decided to hire an assistant. I chose not to go with a tour company because of the high costs, and because we want a fairly flexible itinerary, including some free volunteering and maybe even couchsurfing. So I went to my favorite outsourcing site, (affiliate link) and was able to find an awesome virtual assistant (Cindy) in Australia for just $5.56/hour.

This is the first time I’ve ever hired a personal assistant or outsourced personal tasks. In my business, I outsource programming, customer service, blogging, SEO, and more. And I love it! I couldn’t run my business without the help I receive every day from my team. But personal tasks? Isn’t that too…personal to outsource? Would I just be a control freak and end up doing the work all over again myself anyway? While I’m still not quite ready to have someone answer all my e-mail (when my family writes, I’d like to respond personally, for example), I thought it wouldn’t hurt to get someone to at least help with coordinating multi-country flights, and finding good accommodations and activities.

The Details of the Trip

Galapagos Tortoise

I posted my project on oDesk, including a detailed description of exactly what I wanted, including:

  • Finding the cheapest flights and buses for a trip to Colombia, Ecuador (including the Galapagos islands), Peru, Chile, Argentina, and Brazil
  • The best accommodation in several categories (free/couchsurfing, hostel/B&B, mid-range hotel, and vacation rental)
  • A list of activities and volunteer opportunities in each area with prices and details
  • A list of average high and low temperatures in each area at that time of year, etc.

My entire project description was actually about 3 pages long, with a lot more detail about what I was looking for in each of these areas, including some tips on how to find cheap flights and what activities and accommodations to rule out. (I have learned to be very detailed when outsourcing in order to get the results I want.)

I had about 30 people apply for the job, some for as low as $2.22/hour, but Cindy impressed me the most with her prompt communication demonstrating that she truly understood what I wanted. It’s great working with a native English speaker who understands every nuance and comes from a similar cultural background. She finished putting together the initial flight itinerary the next day, and I quickly realized that I had overbooked us. We weren’t getting enough time in each location, and would probably feel rushed. Plus, the many flights across South America really drove the cost up – I wasn’t about to pay $14,000 in airfare! Buses are an alternative, but I didn’t realize how big South America is! It’s a 30-50+ hour bus ride in between most countries, often through winding mountain roads. I shudder to think how our 5 and 7-year old kids (not to mention their parents) would hold up on a journey like that. But it might be fun to try once; I hear the buses are quite nice.

In the end, we decided to cut out Chile, and save Colombia until the end of the trip, flying directly from there to Orlando through Jet Blue Buddy passes. We’ll get to spend more than a week in each country, sometimes 2, and hopefully have plenty of days “off” to just relax or catch up on work. This is really just long enough to give us a taste of these countries, but we can always come back if we fall in love with a place. Cindy did take longer than I expected on the project, but this is partly because I kept changing my mind about what I wanted. I think I’m going to have her continue helping me with other tasks, too, if she’s willing.

Update (Aug 19, 2010): Cindy just informed me that we need to apply for a visa to Brazil in advance in order to get in. Unfortunately, we don’t have to time to put all the documents together and wait for the consulate to prepare the visa before we leave on our trip, so we’re going to have to cut Brazil out of the itinerary. At least we hadn’t bought any plane tickets yet! We’ll be back to Brazil another time when we came spend longer there and actually learn a little Portuguese.

Update2: Okay, now we’re cutting out Argentina and Brazil to save on airfaire, and to give those two countries the time they deserve on a later trip. This will be a slower-paced trip now, just Colombia, Ecuador, and Peru.

More than a fun vacation

Children in Peru

We’re not planning out what we’re doing every hour, or even every day of this trip. For a lot of activities, I think we’ll wait until we get there and see what feels most appealing at the moment, after talking to the locals. But we have a good list of things to do in each place, and we’ll make sure we get to the major attractions like Machu Picchu and Iguazu Falls. We’re also really excited to volunteer for a week at a school in Peru, Aldea Yanapay!

I hope this will be a great adventure for our family, something more than just a “fun” vacation, although I’m sure it will be fun. I want to meet new people and make new friends, stand in awe of some the world’s natural and man-made wonders, experience new cultures, foods, and sounds, open my eyes to new ways of living and thinking, learn more about the history, language, and life of the people and countries I’m visiting, grow closer to my wife and kids, and hopefully make a positive difference in someone’s life along the way. It’s a tall order, but for some reason, I have no doubt this trip will meet every one of my expectations. And I like to think that I will be made better in the process, too. Oh! How I love to travel!

Brandon is a location independent entrepreneur, musician, worldschooling father, and the principal author of this blog. He's all about reaching his potential and enjoying life to the fullest in each moment.


  1. I think it’s genetic, this love of travel. Your sister is also addicted to the traveling bug. I really love to travel (though would prefer to be able to stand on a transporter platform and just beam myself to the next location, rather than dealing with the airports and long flights). But my love of travel pales in comparison to my sister, Kristin, who was perhaps born with a passport attached.

    I’m hoping to make some lifestyle modifications to enable me to do more traveling abroad… or course, starting with my visit to Costa Rica in January :)

    This looks like a wonderful itinerary. I’m glad you found some help and are pleased with the results. It’s a challenge to find someone who is as competent and thorough as you are, and hard to let go of control… but this sounds awesome.

    Delighted you’ll be able to do some volunteering – I know that’s been a goal since your first trip to Panama. Can’t wait to hear how it goes and see all the pictures.

  2. Oh how I love that you love to travel too! So excited. There is more than one way to plan a trip, and I’m glad you found Cindy to help us out. :) She is doing an awesome job!

  3. Yes, the travel bug. I definitely have it bad. I think I would travel somewhere new every month if I could. For now I will live vicariously through you and your family :) I think it’s great you guys are planning to volunteer in Peru. What a great experience for everybody! I’m sure this trip/vacation will be everything you hope for.

    And I can’t wait to see you guys when you come here. It’s been way too long.

  4. Hey, Brandon! Affiliate link doesn’t work in Google Reader through RSS for some reason.

  5. Hey Brandon, Let me know if you have any questions about Buenos Aires. Tons of museums and parks. Lots of short term apartment rentals for reasonable rates.

    Check out Puerto Madryn for whales and penguins. The whales migrate there from September through December. Took one of my daughters there for a kayaking adventure and it was amazing.

    Long distance buses in Argentina are the way to go. Three classes, semicama, cama and ejecutivo. Cama and ejecutivo are not much more than semi-cama and really comfortable. Much better than air travel here.


  6. Wow how fun! I love hearing about all the neat things you guys are doing. It’s fun to learn about all of these different places I’ll probably never get to.


  7. Great you could get some help making the arrangements for your trip. It should be an exciting, fun and interesting couple of months.
    I’ll look forward to reading your posts.

  8. If you want to go to Brazil you can get a visa at one of Brazil’s embassy locations in South America. I got mine in La Paz, Bolivia and it only took a few days of processing. If your going to a city with an embassy that you’ll be at for 4-5 days it’s worth trying out. Just be sure to have all the documents they need ready or it may delay the process.

  9. @Maxim – Thanks for the heads up. The oDesk link is now fixed.

    We called Brazil’s embassy here in Costa Rica, but it would have taken more time to process (after we prepared all the necessary documents) that it just wasn’t worth the stress. The trip will be a lot more relaxing now, and we’ll just save Brazil and Argentina for a later date.

  10. Sounds like an awesome trip. All the places I want to go to. You will be happy you left Brazil to its own trip. There is so much there, that you could easily spend a month there seeing everything. Have fun.

  11. Wow you kids!! I should have been checking this blog along with Jennifer’s all the time! What an amazing experience for your family. Hopefully whenever we next get to see you, you’ll be able to tell us all the details of how you’ve made this work–I’m filled with admiration!!

  12. Maurine Brug Says: October 23, 2010 at 2:54 am

    Long time reader / first time poster. Really enjoying reading the blog, keep up the excellent work. Will definitely start posting more in the future.

  13. This is a great post and very informative. I need precisely the same services on an on-going basis and promptly created an oDesk account and a job description.

    I’m in the process of creating a detailed project description. You mentioned you wrote a three pager that covered everything you needed. Would you consider posting it or e-mailing to help others to outsourcing their travel plans?

    Love the blog and the great ideas!


  14. Sure, Logan, I’ll send it to you. Thanks for the comment!

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