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Dreaming of cruising the Caribbean

1735 Views 6 Replies 6 Participants Last post by  Greatdays
My wife and I are dreaming (can´t be called planning yet) of taking a 6 months sabbatical and cruising the Caribbean with our 3 daughters (6,8,10). No sailing experience to speak of, just a couple of weeklong charters with captain and a sailing course 16 years ago. However, in trying to understand the feasibility of such a dream coming true, money is an important factor to consider, and a large chunk of it are the boat and acquiring the skills.
My questions (for now) are, If we were to take a 6 month trip (non hurricane season) and never sail again, what's the best way to come about a sail boat, do I have to buy it and then sell it, or is there a market for long term rentals? Second, what's the best way to learn the skills to do such a trip safely?
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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!
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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.
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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.
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Another vote for the ASA classes. But the instructor is everything in these classes so pick a school with a good rep. Even better, pick one in the Virgin Islands and take your wife. THAT is the way to introduce her to the sailing life.
ASA Classes - Best money I ever spent. I took a week long Virgin Island ASA course through a sailing school and it was an amazing experience. sck5 is right though, it really is the teacher you get.
Belize or Panama ASA??

Thanks to all, I will do as you say, so my next step is an ASA course for the little woman and myself. AlanBrown to answere your question, I am from Costa Rica and rented a Condo in Roatan while living in Honduras so we are thinking of taking it up one notch by going for the boat plan. However, your advise is something to keep in mind as an alternative in case cruising becomes too complicated to fit into our current situation.

Virgin Islands is a little expensive and complicated to get to from Costa Rica, does anyone have experiences with the Belize or Panama ASA operations?

Thanks againg for your input.
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