The Hardships of Cruising

Sean, great minds think alike.
I can relate a number or incredible sailing weekends on my small boat. Anchoring out to watch fireworks on the forth of July, anchoring off the lone Cypress at Pebble Beach to watch Tiger woods and Bill Murrey play golf, hooked up to a mooring ball to go to the First Night Celebration in Monterey, anchored off Angel Island in the SF Bay, All are a weekend sail away on a small boat, and all are a part of cruising.
Islandbound, just because you are close enough to commute to work durring the week, does not mean you are not cruising. Spending a month on the hook in San Francisco Bay, sailing up the Delta, and to all the interesting areas in the bay is a real adventure, and you can dinghy in and take the train to go to work anywhere in the bay area.
Just some ideas to get your feet wet. I am sure that there are areas within reach of your location that would lend to some great weekend sails on a 25 footer. You may have to forego the water maker and wind generater, but even a boat that size can be made quite comfortable for the short term.