Let's clarify some terminology- there is "sailing" and there is "cruising."
Sailing is fun. Cruising is a different kind of fun, requiring a different mindset.
Sailing is like driving a 10 000 truck down a winding icy mountain road with bald tires and no brakes. if you know what you're doing, or believe you know what you're doing, it is a whole LOT of fun. If you're clueless, it can get real unfun real quick. At the very least, start by crewing on a boat during the local clubs regular weekly races. EVERY skipper is ALWAYS looking for fresh railmeat, either to replace crew or to simply find a greenhorn who doesn't know that the skipper is a moron.
If you like it, then consider buying a boat of your own, and take at least a basic keelboat course so you aren't a danger to yourself or others. You're boating in a busy area. Remember: big truck, downhill, icy, no brakes, bald tires.
Don't work backwards, and buy a boat then decide whether you are going to like it.
Once you're good with sailing, now it's time to find out how you feel about cruising.
How do you know if you'll like cruising?
Try a cruising simulation:
1.Empty your clothes closet and dresser into the tub. Turn on the shower for 10 seconds.
2. Remove clothes, pack in garbage bags, park them in corner of your kitchen.
3. stuff a phone book under one leg of the table and smaller books under one leg of each chair. Every couple of hours, move the books to different legs.
4. Make sure there are fewer chairs
5. Remove the hot water knob. Leave hot water dripping slightly.
6. Remove three burners from the stove
7. Unplug the fridge.
8. Remove the toilet seat. Take toilet seat to kitchen. Put toilet seat on 5 gallon bucket. With a book wedged under one corner. Bathroom is now off limits. Except for fully clothed cold showers. Twice daily.
9. Sleep on the countertops.
10. Set all timers and alarms
in house to go off at random times.
11. At least once a day, tear up three $100 bills.
12. Carefully plan your meals. Remove all other food from kitchen. Take one quarter of your provisions and place in sink under dripping hot water.
Lock yourself and your spouse in the kitchen on Friday night. If both of you come out and at least one of you is smiling on Sunday night... you might like cruising.