Here are the steps I would take:
- Wordpress is a great CMS for those who are new to CMSs. It's free, it's easy, there's great a great support community.
- Find out which pages on your site are getting traffic (check your analytics)
- Determine which pages on your site have inbound links (SEOmoz has a great module for this)
- Copy the content on these pages to your new site (inside wordpress, or whatever CMS you end up using)
- 301 redirect the old URLs to their new home inside Wordpress
- Create a sitemap for your new site