Cruising World Magazine - Cruising World is a magazine for "cruisers" - people who sail full time - and wannabe cruisers. The print magazine is (in our opinion) better than the website, but we like to check out the articles and pictures.
Cruiser's Forum - I signed us up for this forum a few months ago and was initially intimidated by the number of people there who can call themselves real sailors. I was afraid to post anything for fear of being laughed out of the discussion (at that time, I had no idea what terms like "tack," "jib," and "spinnaker" meant). Now that we've taken sailing lessons and done a little sailing on our own, I've started commenting on some of the posts. This site contains a lot of advice, a lot of encouragement, and a lot of messages from people who desire to live off the beaten path. It's nice to know we aren't alone in that respect.
SetSail - This is a collection of blogs written by individuals, couples, and families who are currently sailing. It's a little slow right now, but it should pick up in a couple of months. Our favorites are the family blogs, as we'll eventually be sailing with our son.
Seven Seas Cruising Association - This site is really for people who are already cruising, but it has a discussion area for sailing and finances. Oh, and it provides updates on piracy issues.
Sailboat listings - I spend way too much time looking at this site. Still, there *are* a lot of great boats out there that don't cost a ton of money. It gives me hope.
These sites serve as reminders that help keep us focused and hopeful.