Do you like to be well prepared before starting on a new adventure, or do you prefer to jump in head first and learn from your experiences and mistakes. Both can be extremely educational, and both will lead you down interesting paths. 

   When Eben first started sailing he chose a 50/50 of the two options, he read one encyclopedia and then jumped right in to sailing. It gave him 6 months of wild adventures with his buddy Jordan; it also gave me a horrific maiden voyage

   However you choose to prep for your next trip, knowledge, however you acquire it is a step in the right direction.

Question posed: Do you have any suggested books to read prior to leaving to sail the Caribbean?
   There is a pile of technical books and encyclopedias that we have onboard in case we need to learn how to fix something or learn something. We have opened them a handful of times in our five years of sailing. We use google more than we use these books! So I can say you could probably do without a lot of these. But they did majorly save our butts once, when we were in a crunch, without wifi, and were clueless as to how to hip tow a boat with a dinghy. Due to this we are hesitant to throw them out. 
   One that we were told is a must, which is almost the Caribbean bible of sailing, is Bruce Van Sants’ Gentleman’s guide to Passages South. We are SO glad we bought this. We have used it extensively, took his advice to heart, and it was always out in the cockpit with us for every sail from Miami to Puerto Rico. Unfortunately that is where his book ends, in PR. For everything from there on we have been using the Cruising Guides by Scott and Doyle for the Virgin Islands, Windward and Leeward islands. They are very informative about all the anchorages along the way, the hot spots to see, and the local history. We HIGHLY recommend all of the above books. They were crucial for us.

Other Subjects

   If you are trying to wrap your brain about food storage, meal prep, cooking, and recipes, and how all of that works on a boat, The Boat Galley Cookbook is a great source of knowledge (it’s more than just a cookbook). I don’t own my own copy, but I will admit to reading over Windtraveler‘s and writing a bunch of the recipes in my little notebook. Shhh don’t tell Carolyn and Jan! The blog is also a huge wealth of information and is definitely worth checking out. There are new posts almost daily.
   There is also this other book, which I haven’t read yet, but was asked to send in a few excerpts for (not making any royalties on it!) Voyaging with Kids was written by three boat families to answer the A to Z about sailing with children. You may want to take a peak at that before jumping in head first yourself.

   I am sure that are 101 other books other boaters can recommend, but with Van Sant, Cruising guides, and Google, you are pretty much covered.