My dad bought a C&C 27' Mk3 sailboat last year. We haven't been on any long excursions yet, though it's been nice to just sail around.
If you guys are comfortable enough sailing, you should totally do some sort of trip. I don't know where you are, but I bet there are some channel islands or barrier islands to head out to. Get a friend to join you and you guys could sail nonstop. If not, you can just drift while you sleep. I have worked on boats my whole life, but I had never been out far enough to just cut the engines, turn on the proximity alarms, and pass out for the night. It's pretty soothing.
After getting my sailing experience in on someone elses boat and dime, I dream about getting a ~35ft mono-hull and cruising around the Caribbean, if not pulling a transatlantic crossing. There is such a cool culture around it. I met so many sail-bums who just crewed boats aimlessly, and met a few more respectable fellows that captained boats to destinations as a job.
Obviously, I would go bigger and swankier for my dream craft, but I can see kicking down $10k in the next few years for a boat in decent shape. How else will I ride out the initial wave of zombie apocalypse.
I ended up meeting the guy I sailed with in a harbor bar while I was bumming around latin america. I had nowhere to be, so a couple beers later, I was on the docket as a crew member. I'm glad he wasn't smuggling coke, or rather, I am blissfully unaware of it if he did. I have never been through such customs bullshit as floating into Key West. They separated us and put us in interrogation rooms and left us sitting for a good two hours. I answered everything with a smile despite being treated like shit, and I suppose it's their job more or less, but goddamn. US Customs can suck it.