Dreaming of cruising the Caribbean

It sounds as if you're in love with the idea of escaping somehow to "The Islands", but are not necessarily interested in owning a boat or making a long-term lifestyle change. Nothing wrong with that. Many of us dream daily of white sand beaches, palm trees, and cold Coronas. (Hey, didn't I see that on TV?)

My question to you is why does your escape have to involve a boat? Why not rent a shack on the beach for a few months? Why not settle in there, enroll your kids in school, and get to really experience island life up close and personal? You don't need a sailboat to do this.

I have friends who headed for the islands years ago. They do not own a boat, but hey have rented and worked in Puerto Rico, Aruba, and now live in St. Thomas. They are living the "Island" lifestyle, boat-free.

If you remain committed to the idea of cruising, my advice would be to get charter certified, charter a couple times with your family, and see if you still have the dream. If so, start boat shopping.

Good luck!

You should take a bareboat charter certification class to brush up on your sailing skills and learn navigation and boat systems. I recommend ASA since I am an ASA instructor. You can find a sailing school near you on the ASA website: Learn to Sail and Earn Your Sailing Certification With the ASA

You might be able to lease a boat long-term by contracting with an owner of a boat coming out of charter. Often those boats go up for sale and don't sell right away. The disadvantage of doing that is that it won't be outfitted for cruising, and will have the bare minimum for electronics. You might be able to purchase a boat that someone else has already been cruising on, then turn around and sell it when your cruise is finished. Some friends of mine did that, owned the boat less than 3 years and sold it for almost what they bought it for. To make this strategy successful you need to choose a boat that is in high demand. Work with a broker and letting him/her know you'll be looking for a buyer within a year.

2nd the ASA type sailboat class even if you do not buy a boat! Few charter companies will charter for that long of a period and some have area limits that may not fit yours if you want to do more island hopping. Best bet may be a private owner charter.

You really need to know if your family actually shares your desire to spend 6 months on a boat. I personally would hate to be near a boat with 3 kids who were unhappy with the routine and closeness that you will find on most boats under about 50' and then even that large can get small after a week or so.

You probably need to do a lot more planning on where your going to start and where you will be going and what the conditions are at that time of the year for that location. For a 6 Month non hurricane trip means you would be in the islands somewhere between late November and June. Depending on where, that could be a lot of different type weather and sea conditions in those months.

Your ASA type classes for certification will answer many of your technical issue problems but not the family ones! Your wife should be capable of taking over if you become disabled and she would do well in also attending these classes. Another option is to possibly take a vacation/ certification sailing class. Not sure they would accept children but you could check out private classes with most schools. I know of may couples that attend and have a great time. You may consider this as a introduction to your wife if arrangements need to be made for the kids to stay home for the vacation / class.