Personally, I like to do a bit of everything...which is in my nature (why I eat a lot of combo platters too...lol).
I am lucky enough to have a slip at my house, so most of the time, the boat sits there, ready to go in 5 minutes. This is really fun for those windy days when you might have a couple hours here or there to go for a quick sail. I am not on open water though and I have a 0.5 mile canal to go through and then a 3 mile somewhat narrow channel before I get out to good sailing grounds (although I usually sail the channel in one direction or the other). The Mac cut about 1-1.5 hours off of my quickie sail time that I used to have with my former keel boat...with that boat, there was a 3 hour minimum time to have any fun.
But another thing I will do at times is rent a short term slip somewhere else..like out in the Gulf. Beaches in my part of the bay are not all that nice, they are ok for a while, but they get old compared to what is available in the Gulf. Many marinas don't like to do short term rentals (up to 1 month) but if you find one with empty slips, you may be able to talk them out of their usual "policies". So, this is kind of cool, put the boat at a new place, explore for a few weeks, and then go home. This also makes it easier to do "day sails" from a more exotic location.
Of course, the trailer is nice too and we will sometimes keep the boat on the trailer for a couple months and during that time, take it someplace just for the day. We are still working on a multi-day trailer trip. Good point above with the people who come and talk to you on the ramps though...a real time killer that is..but I hate to just cut someone off too, when they are enthusiastic and interested in my boat. So, in reality, it does take longer than the "checklist". I know all about checklists as I am a pilot too (although inactive these last few years)..by the time you do all the hangar talk, park the car, pack your lunch, etc..it always takes longer than the operational "checklist" you have to go through to actually get the plane off the ground. Yes, if I were really disciplined, put some blinders on and didn't do anything other than what was absolutely necessary, I could go fast...but how much fun is it to rush..this is supposed to be a leisure activity afterall.
Anyway, I have been systematically modifying my boat now for 1.5 years to make things go faster and this is helping considerably. But still, there are a lot of peripheral activities required to get a family of 6 out on the water, and the preparation time is proportional to the amount of time you will spend on the water. Everything from planning the meals, packing the coolers, finding all the cords for the cell phones, emptying the pottie out because your 3 year old must use it, even if only on the boat for 5 minutes, etc. Those of you without kids have it pretty easy as far as this goes, you don't have to pack all the beach buckets, shovels, containers for the shells, etc.
I know, they will get older and hopefully start helping more. See, unlike Duane and his family, I have this mentality that if I don't make it fun for them..ie, in terms of doing most of the work, they won't want to go anymore. With younger kids, you also get caught in this quagmire that it will take much longer to teach them something than to just do it yourself and get out on the water. I know that this is wrong in the long run, and I am slowly trying to remedy it..mostly by going out with one kid at a time so that the frenzy of the whole family isn't there to raise the stress level.
But then there are also the safety issues, for example, I can't have my 4 year old daughter helping me raise the mast...even though she is probably the toughest one of the bunch. She was great last weekend when we would get caught in 22+ mph puffs and heel over to 35 degrees for a bit. "see Daddy, I'm holding on tight" she will say as she grabs the lifeline with both hands and things that I didn't secure well are flying around in the cabin....my wife would have have had us heading back for home with the engine about then. I pretty much have to keep it around 10 degrees or less when scream-o-meter(s) are on board..otherwise, they don't have any fun and I don't get to do what I enjoy.
