I would like to give you a little encouragement. If you want to include over the water transits into your itinerary, just get yourself to where boats are getting ready to leave. Grease your chain, a bottle of vaseline will do wonders. Strap it to the leeward shrouds and off you go. Most trips will just be a few days at most.
Be cheerful and willing to take the wee hours watches, offer to cook and bring some grub. You will be fine. I have taken bikes, drag queens, air conditioners, scooters and even a washing machine - just because I wanted to do it. Remember - opportunity is where you find it and in your case, it will not be in Central Mexico at a Wifi hotspot but at the marina/yacht club.