Good on you for taking the plunge! A big step quitting your job to do this. Agree, do it when you're young, traveling the U.S. on motorcycle has been #1 on my bucket list for over 30 years, I keep putting it off. Now I'm 55 and have finally realized I have to put more effort into making it happen since I'm not sure I'll physically be able to do it when I retire.
I'm also a teacher (music), ride a DL650, and live in New England (Nashua). My best friend growing up was Greek, his family took me there one summer, a phenomenal experience. The blog looks interesting, I'll be following.
2009 Wee Strom ABS (current)
1987 Harley FXR Low Rider Sport (current - with 206K miles)
2009 Aprilia Mana 850, 2006 SV650, 1984 Yamaha Virago 1000 (all sold)
Silver Strom Club Member #11
Wee Farkles: Russell Day Long Seat, Madstad with Moose Adventure Shield +4'', SWMotech Centerstand, 1'' up & back bar risers, Givi XS308 Tankbag, Aprilia mirrors, Framesliders, Fenda Extenda, Elka Shock.