You''re not stupid. This is just the way I started cruising, except that I went solo (so who''s stupid now, huh?). I spent two weeks living and coastal cruising a Catalina 22 in a Long Beach-Santa Rosa-Catalina triangle. Here''s what I learnt:
1) Pack everything as if the boat will be turned upside down and shaken violently. I had the fun of seeing everything I owned go flying across the salon whenever I was heeled over hard (what I didn''t see was what was happening to my battery and fuel cans belowdecks!). After two days, I had stowing gear down to an art. Bring many shock cords of all lengths/diameters: they will be like babysitters for all your gear. And little brass eye-hooks that will screw into your woodwork inside the cabin, to hook the cord onto. Of course, you must also put everything away as soon as you''re finished with it, or expect to see it on the decksole later.
2) Have charts and a good coastal cruising guide. You can practice a bit of navigation with just a folding compass, a walking ruler and pencil (and then see how accurate you are with the GPS). A hand-held compass is useful for taking relative bearings along the shore and finding where you are on your chart, and for taking sightings before and aft of the beam along shore to see if you''re dragging anchor. Cruising guides have a storehouse of great information at your fingertips, esp. about good anchorages along the way. This can turn a long, cold, windy run all the way across Santa Monica Bay during a Small Craft Advisory into a cozy anchorage in Paradise Cove at the foot of Pacific Pallisades, only because you know where it is. Choices are good. Since you''re familiar w/ Channel Islands, you know Pirate''s Cove is not the only place you can run to when the wind is up. Learning a bit about navigation/piloting was one of the most satisfying parts of my first cruise. (The day I crossed the channel from Anacapa to Catalina they were recalibrating all the GPS satelites, so I spent all day out of sight of land, relying on my chart-figuring done the night before and my boat''s compass. I was dead-on to the Isthmus. I''m glad I had practiced for a few days before I really needed it).
3) Tacking upwind is tiring, wet work in a small boat. Take that weekend trip, but just go down the coast a day. Then feel how different it is beating your way back up to Ventura. Divide the number of coastal miles from Cabo San Lucas to Homeport by the number of coastal miles you made good beating into weather, and you will know the number of days you''ll be sitting at the tiller pounding into swells that are higher than your deck, wishing you''d reduced sail an hour ago. It will make going only as far as Tijuana sound like a great idea. Green water washing over the cabinhouse into the cockpit? Hope you brought a jacket. . .
5) A whisker pole to keep your headsail filled while running downwind is one of the beautiful things in life. You will make up a happy song the first time you see it work. It''s worth twice the price you will pay for it. I''d go without food for a day just to have one with me.
4) A good Coleman camping ice chest will stay cold 3-4 days, if you don''t open it constantly. Plan stops at marinas for ice/shopping accordingly. Block ice lasts twice as long as cubes, if you can find it. Deli meats don''t live very long in a cooler. Cutting a piece of insluation to fit inside the cooler, across the top of the food, will extend ice-life. I used an old kickboard.
5) Have absoultely clear expectations about what you and your crew are going to be expected to do: how much time @ tiller, how long your working days will be, who cooks for whom at what times, who''s hoisting and dousing sail, etc. Make all important decisions together the night before you''re likely to have to make them (like tomorrow''s first choice distance/destination and an alternate). You both need a big picure of what''s going on. (Okay, I didn''t have to worry about this singlehanding, but think about trips on your friend''s 30 and how easliy misunderstandings happen. For every foot of boatlength under 30'', multiply aggravation factor by 2).
6) Tools and spare parts are essential. Have a good supply of electrical and rigging parts and pieces, and the handtools to use them. Don''t forget thrust pins for the outboard (right behind the prop). My own Honda seems to like to snap them. I replaced more than one of these in two weeks.
7) Plan some "days off" at anchor to repair & maintain equipment, sails, and just relax. Take half a day to see the Aquarium of the Pacific in Long Beach and grab a burger, or whatever, then continue the next morning. Don''t be like your dad driving across country on vacation, trying to make "good time." You''re purpose is to enjoy yourself, right?
Okay, some other random thoughts:
a) you will need some way to recharge your battery (assuming you have one: if not, bring plenty of spare batteries for all of those hand-held radios/receivers you mentioned). Sometimes you can get shore power if you rent an overnight slip, so an auto battery charger (and a shop-grade extention cord) is just the ticket. Consider installing a good solar panel. They really work.
b) 10 gallons of drinking water sounds like just enough for two men for 3-4 day stretches You get dehydrated quickly on the water. The wind itself draws water from your body. For drinking, I''d use the rectangular 2.5 gal. containers with the pull-spigot and handle that you see in the supermarket, instead of 5-gallon jugs. They will stow anywhere and won''t fall over and spill. Don''t punch an "air hole" in the top when you use one, so that it won''t leak. For non-potable water, you can conserve it several ways. One is to wash dishes/utensils with seawater, and then rinse using a spray bottle of fresh water. It sounds ridiculous, but it works very well. If you make sure that everything that touches your ice chest''s H2O is clean, you can even get cold drinking water from the drain plug, assuming that you''re not doing things like throwing open packages of bologna into it. Try this out on your next daysail. Just make sure things are rinsed off before they go into the chest. And know that when you drain your ice-chest, you are draining "cold" from it, even if it''s melted "cold."
c) good luck installing enclosed heads on a 20'' weekender. You mean complete with plumbing? Treat your chemical toilet well, and she will treat you well. I think it would be less inconvenient to use that for a while than to remodel your boat. I slept next to mine the whole trip, and never knew it was there when I wasn''t using it. Keep a small bucket or other container (or even better, an old rubber hot water bottle: it won''t spill) handy just for urination, especially during the night. That''s when you don''t want to be fumbling around with a chem-toilet: in the middle of the night, in a pitch-dark cabin with no room to stand, bobbing on every little swell, trying not to wake your partner, pulling up boards from the V-berth, with an urgent call from Mother Nature threatening to make an emergency breakthrough? And how are you going to make sure of you''re your aim in the dark? Get the idea? Now stop laughing at my hot water bottle. Real convenient while beating to weather, too.
d) consider a small inflatable tender. Maybe only blow it up at places you stop at for more than a day. Think: if all moorings are full, you will need to get from your anchorage to shore SOMEHOW, and swimming while holding a bundle of dry clothes over your head lacks a certain panache. Besides, how will you bring stores back to the boat?
e) stow enough fuel to motor two full windless days @ half throttle. Besides, you may actually want to make some distance before noon along the California coast. I believe your boat is a light-air performer. I don''t believe it''s a no-air performer. It''s not un-seamanlike to motor through a duldrum morning, if you''re trying to get somewhere. At night, drop the hook.
f) little conveniences will make the difference: a radio (plenty of batteries), books, etc. will make living aboard a weekender more tolerable.
g) find out about any documentation, etc. you will need at your Mexican port-of-arrival. Even in California, harbormasters sometimes asked me for a copy of my boat''s registration to match to my ID when renting a slip.
h) you''re going to need more anchor line: I''d double what you have for each anchor, or at least be able to snap-shackle those two lengths together, but then you will only be able to throw over one hook, and that''s dicey.
i) throwing some chain ballast down below can''t be a bad idea. Do it. Just watch your waterline on a small boat like that.
j) choose the person you take along carefully: a month on a tiny boat will strain the best of friendships. In the end, you will know everything about him that bothers you, down to small mannerisms and smells. Stay flexible and light-hearted.
k) in a little open cockpit like that, you will want to stay warm and dry. Invest in some type of bad-weather clothing. If you get wet, you''ll be miserable for hours and hours.
l) always eat breakfast. It gets blook sugar up, gives your muscles fuel, and gives your brain glucose to burn. You''ll be stronger, faster, and clear-minded.
I think you have a great idea, if a bit ambitious. I''d just make my first cruise in that particular boat a bit shorter. Try San Diego and back, or Tijuana. Your crew may not be as gung-ho as you. You''ll still have plenty of experiences that will make you a better sailor, and will still have some great stories to tell those other friends who backed out!