Had an interesting dinner-time discussion last night with my wife. To make a long conversation short we are now working on plans to cut our ties to shore and go cruising.

No, we aren't cutting out tomorrow or next year. This is a ten-year plan. There are several major steps we need to cover along the way, if all goes great it may happen sooner than 10 years but our goal is not later than 2018.
A bit of background, we are both in our mid-30's with two boys (4 and 2). I have some sailing experience, mostly dinghies (Laser, FJ, Capri 14, Harpoon 5.2) and a few summers as weekend crew on a Freedom 28. My wife has been sailing several times keelboats primarily on San Francisco Bay and most recently in the Harpoon 5.2 on Lake Michigan. She really enjoyed the recent sails. Better yet, the kids enjoyed the sailing.
I wish I had gotten my own boat years ago but my thoughts of living aboard in Alameda, CA were disturbed by large student loans and a job in Germany, then came grad school, more loans, house, kids, etc.
Jist of the conversation last night was - why are we working so hard to earn money to save for retirement when we might not be healthy enough to enjoy it then. Therefore, let's take a multi-year break in middle age before the kids head off to college and have some adventure.
So, the major tasks in front of us:
1. Improve sailing skills - both of us need to get more experience, probably starting with some formal training.
2. Sail regularly - time to head for the lakes, maybe buy a small dinghy or rent keelboats.
3. Get ocean experience and explore boats - time to charter
4. Increase the sailing kitty - this seems to go against the 3 previous steps
Stay tuned for further adventures!