waterbat, I sailed Newport to Bermuda 4 times on a 31' kit boat that I finished myself. Also I sailed in one leg of the Bermuda 1-2 race on a 30' racing boat. That one made me a little nervous mostly because it was so light, we were traveling at speeds that were on the verge of out or control and we where flying a spinnaker at sea or where until a mast head shackle broke on my watch one night.
It can be done fairly easy if you have the skill; equip the boat properly including safety gear; have a sea worthy vessel and some good luck. If this is an idea that was recently thought up and you do not have the experience or finances to do it properly.....well good luck....I hope to see you and trade some sea stories in San Pedro.
I met a guy in St. Thomas one time who sailed down the Amazon and up the Eastern Caribbean on what was not much more than a canoe with a mast. We let him sleep on my boat one night so he could get some reasonable rest. He woke up very early left me a thank you note and the last sighting of him by me was way in the distance on his way to Culebra, PR. I hope he completed his journey safely.
Funny, my daughter chartered a boat the other day for my wife and it as a Christmas surprise present. It had a captain and I wasn't aboard 10 minutes when the capt. told me it was his dream to sail over to Mexico and down the coast of Central America with his wife and 2 dogs. We had a good conversation for a few hours.
Somewhere on a beach in Belize