Re: Where in the world to learn in August?
I've seen good results (wife) from Colgate's Offshore Sailing School. Tortola is a great place to sail. They have a school in Fort Meyers/Captiva as well. Ask them what happens if a tropical storm ruins the trip. Can't be the first time they've dealt with it. Typically, you're going to have many days notice of the potential.
While it is hurricane season, the odds are actually in your favor that you won't get hit on a single week in a specific location. But, best to know the deal if one is on the way.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.