We just returned from a 15 day vacation in the Rockies that was truly a vacation; I checked my email once or twice a day and did very little work. The trip we just booked to Mexico, however, won’t be a pure vacation nor “mini-retirement.” Rather, it’s our first big test of how well I can conduct my business from a remote location.

Thanks to a comment left on my cheap travel post, I’ve been using Kayak a lot lately. Today I booked an incredible deal on a multi-city itinerary. Check this out: Chicago -> San Francisco -> Guadalajara -> (stay for 3 weeks in Ajijic, then bus to Sayulita) -> Puerto Vallarta -> Salt Lake City -> Chicago. Total price with taxes and fees and paper ticket shipping: $568.89. Unbelievable. After spending 2 or 3 weeks near in Ajijic near Lake Chapala, we’ll take a bus down to San Pancho and Sayulita for another 4 or 5 weeks. After that it’s back to visit family in Utah for the holidays before returning home to Chicago.

I still use Travelocity when first checking for the lowest price on trips that have completely flexible dates. Once you get it narrowed down to +/- 3 days, Kayak is is the way to go!