The Problem:

My brother and I like to ‘freestyle’ travel.

Once a year we choose some spot on the globe, buy roundtrip tickets, and explore the place without any preparation.  No hotel reservations, no guided tours, no one to escort us around town.

Just show up and survive!  As you can imagine, our trips are full of unplanned adventure.

The difference between a good vacation and a great one is usually determined by one important variable:  how quickly we meet someone in-the-know.  Guidebooks are informative and useful, but meeting a local who can recommend things to do and places to go is infinitely more productive.

So how can we leverage technology to improve our travel experience?

The Solution

Before you purchase your tickets, check out Kayak.com.  It will run your itinerary through all the major travel engines, ensuring you get the best price.

If I’m headed to a large city in the USA, I usually try PriceLine.com for discounted pricing on five star hotels.  Go straight to the section for naming your own price and bid ridiculously low.  It works well in places that are undersold, like LAX.

CraigsList.org is a good place to search for vacation rentals.  For example, hotel prices in New York start at about $200 for a night for a depressed property.  On CraigsList, you can get a clean, fully furnished, one bedroom condo for just $150/night.

TripAdvisor.com is a good site for getting feedback on places to stay and things to do.  I also like the ’36 Hours’ section of The New York Times (nytimes.com).  Be sure to drill down into the readers’ comments.  You will find good insight there.

Lately I’ve become a fan of Yelp.com – especially on my iPhone.  Yelp provides user generated reviews of everything from best place to get a sandwich to finding a gym for a quick workout while on the road.

The iPhone has a built-in GPS, so after choosing Yelp’s recommended place for breakfast, iPhone will display your real-time position on a nice little map, helping you navigate to the target destination.  It works very well.