“It’s just too hard…” People often say to me. “…the airport security strip search, the extortionary bag fees, the long flight, my knees being crushed against the seat in front of me, customs, immigration, not knowing the language or the currency, the hassle of transportation, the fear of being ripped off, and then there’s the [...]

Travel back in time with me… May 2006 I was starting to plan my traveling career break. I was a novice. I had never traveled for longer than a 2 week vacation, I had never stayed in a hostel, and I had never backpacked. I didn’t have any role models who had done something similar. [...]

It’s time for a little Sherry update. I try not to do these too often so that I can remain a mystery and therefore more interesting…but here goes – the mystery is revealed in a short post. Where am I now? I’ve been in Boston now for 5 weeks house-sitting and haven’t really written a [...]

“I wish I could do that.” A phrase I have heard often regarding people’s reaction to me quitting my career of 14 years to go travel around the world on a mini-retirement. Normally this phrase is followed by “but…I have a family/house/pet/no money/insert dream killing word here…” This ‘wish’ is the sole reason we created [...]

The Iceland volcano grounded air travel in Europe last week; it was a frustrating week for travelers. I know their pain because I too am grounded…here in the US. I’m waiting to travel. It’s hard for me to stay grounded and be patient waiting to travel; I have trouble taking my own advice -> Have a [...]

If you are going to travel around the world, it requires patience. I hear from many people who want to travel, but they have to wait for the right time to begin their journey. Sometimes they have to wait for money, for a school degree, banking enough time off, for a wedding, for a child [...]

I get many emails from travelers all over the world asking me questions about my travels.  Here are some of the recent ones that are great to share with everyone!  If you have a question, don’t hesitate to ask! Q:  from Dave – Brooklyn I came across your blog and was very impressed by your [...]

I recently realized that I have been without a ‘typical’ job now for longer than I’ve ever held a job at a particular company – 3 ½ years. My typical length at an employer was about 3 years before I would move on and up. I’ve been traveling and  blogging now for 3 ½ years; [...]