Originally Posted by funsailthekeys
To be quite honest it would be cheaper and less wear and tear on the boat to truck it to Texas and leave from there.
Deacon, Welcome to SailNet. There's definitely something to be said for the advice above, although if you're going to the trouble of shipping why not go all the way to Florida and save a transit of the Gulf of Mexico (not much to see there).
I researched (but have not sailed) most of this route when we had our boat in the Pacific and needed to get home to New England. The route is long and some parts of it would not be much fun.
West Coast to lower Mexico -- no big problems here presuming you leave SF in late summer and move on to Mexico in November. Mostly just a series of coastal hops of several hundred miles each.
Central America -- Crossing the Gulf of Tehuantepec requires a good weather window. Winds from El Salvador to Panama are variable and can be very light requiring time on the engine. There are numerous places to anchor and provision along this coast.
Panama -- The passage from Cabo (Punta?) Malo to the Canal is often a bash to windward, but it's only a hundred miles or so. The Canal will cost something just above $1000 by the time you're through to the Caribbean. One issue is that you need to be able to make six knots under power -- they will tell you the minimum speed is 8 knots, which you'll have to say you can do, but they won't push you much above six during the transit. If you can't do six knots and if you miss a lock transit, it can be very expensive.
Panama - Belize -- an offshore route is best and not much fun until you reach Belize as you'll be challenged by headwinds and contrary currents much of the way.
Belize to the Caribbean -- best done by coastal hops passing west of Cuba and on to southern Florida. Hence, Bahamas and Thorny Path to the USVI. This is a weather sensitive route -- wait for winds from the right quadrant and scoot to the next place before the wind changes.
Given the size of your boat my guess is you would be hard pressed to do it in one winter season. Some of these areas offer nice cruising gounds (Costa Rica, western Panama, Belize, etc) so it would be a shame to rush through them. Assuming you leave the US in November, you would probably want to spend the next summer in Costa Rica or Pamana and continue on into the Caribbean in November of second year. It's not a good idea to leave Panama before November as many late season storms are spawned in the western Caribbean.
When we planned the trip I was planning to leave San Diego in November and be in Florida in early May and then on to New England in late May or June. That's do-able if you've got good speed and range under power, but if you arrive in Florida in May / June, you wouldn't want to go much further until the hurricane season is over in November.
So you can see, it takes a lot of time and puts lots of miles on your boat (miles that won't be without cost in wear and tear). Add in the cost of the Canal and a couple of extra years of insurance premiums, and you're probably talking about a considerable percentage of what it would cost you to "truck it". Putting a boat on a truck on the west coast in late October / early November would have you in the Bahamas / Caribbean by Christmas.
Think hard about how much time you'll have and whether you'd rather spend that time on Central America's coasts or in the Caribbean.