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Bahamas cruising in a small boat
We did a similar trip in a Crealock 37 with six foot draft, and there were times when a smaller boat would be nice. If your boat is seaworthy, size truly doesn''t matter. We saw people sailing on Deerfoot''s and Catalina 22''s, and we all watched the same sunsets, caught the same fish, and walked the same beaches. Comfort and storage are issues, but hopefully by now you have been on your boat in bad conditions and are happy with how she behaves. Storage issues are solved by going light and simple. Lot''s of pros and cons, but ultimately, you will be happier going now with what you have than staying ashore and wondering "if." I never met a single person cruising who had any regret other than not doing it sooner.
One caution I would give you is that you shoule give the weather a healthier respect on a smaller boat. Be prepared to wait in Miami as long as it takes to make the crossing. There is a small and conveniant yacht club (the Miami Yacht Club)where you can anchore and wait (and wait, and wait...).
Otherwise, GO! I have downsized to a Dana 24, and would gladly take it around the world if I could convince my wife...