i'm on a similar path. never traveled much in my pre-er life. just the caribbean, bahamas, some northeast areas and florida. so i am not at all acclimated to travel.
i'm easing myself into it with roadtrips around the country. so far did blue ridge mnts, smokys and a trip up and down the east coast. next i will try summers away in a foreign land like three months in toronto. if i take to that i'll try going farther offshore.
within 3-5 years i see myself selling the house and becoming a perpetual traveler, living in each place for a minimum of 3 to 6 months. my goal is not to go around the world but to get a better sense of where i am so that by the time i die i will know where i was. i can think of at least 20 countries i'd like to experience and at 6 months each that alone would take 10 years.
anyway, that's the plan. now to see what life has in store.
there's tons of information on the web to get you going. when i first started researching i thought i could just bop around the planet and stay anywhere as long as i liked. but it doesn't quite work like that. so one website i find particularly useful to get an idea of the logistics of perpetual travel is
Visa and embassy information for all countries - Projectvisa.com.
another one i like a lot is
www.cia.gov/library/publications/the-world-factbook/index.html which gives really good information on each country.
there are also considerations for someone like me who is gay and would rather not find myself dealing with too much homophobia. for instance, i thought i would like to spend some time in belize until i recently came upon this article (referenced by some one on thorntree)
Belize News - Belize's Leading Newspaper | Belize's Breaking News - Amandala Online
and so for my special needs there are websites which monitor homophobia worldwide such as
LGBT rights by country - Wikipedia, the free encyclopedia and others.
so far my approach is working well for me. my first roadtrip had me running quickly back home but my last one kept me on the road for two weeks. i also find that i was happier traveling than i am in my house. this home just isn't what it used to be. time to hit the road.