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How far do you want to drive? You can rent them in Melbourne at the Hobie dealer, and sail in the inter-coastal Indian/Banana Rivers (really lagoons) Usually have 10 to 15 knot winds in the afternoons. As far as O'town, I can't help you. Mickey may rent them, but I don't know for certain.
I found this by doing a "Google Hobie rental in Orlando" and this is one thing that popped up
Not many people seem to know about it but there's a small marina on the lakefront near the Comtemporary Resort where you can rent boats. 12' Sun Fish Sailboat 2 guest maximum $9.43 per ½ hour 14' Hobie Cat Sailboat 2 guest maximum $11.79 per ½ hour My niece, who is mad on sailing wanted to do this.
The website says: "Please present a Walt Disney World Resort ID Card, passport, or a valid driver's licence. Sales tax not included. For information on specialty cruises (seasonal) or additional recreation offerings, please inquire at the rental window, touch 57 on your WDW Resort room phone, or call WDW-PLAY." *Requires reservations.
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TC
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