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 Low Rider Sport (current with 200K miles)
2009 Aprilia Mana 850, 2006 SV650, 1984 Yamaha Virago 1000 (all sold)
Silver Strom Club Member #11
Wee Farkles in order of importance: Russell Day Long Seat, Madstad with Moose Adventure Shield +4'', SWMotech Centerstand, Givi XS308 Tankbag, Aprilia mirrors, Framesliders, Fenda Extenda, Elka Shock.