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Anyone know of Caribbean resort areas where one can rent a boat for day sailing? I know there are a zillion beach dinghies for rent, but they generally don't want to you sail out of their line of sight. There's also endless bare boat charters, and crewed tourist trips. What I'm interested is none of that, but just a decent 20' to 30' sailboat I can rent for a day while my significant other cruises the jewelry shops and related things on shore.

Thanks

GJ
 

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Anyone know of Caribbean resort areas where one can rent a boat for day sailing? I know there are a zillion beach dinghies for rent, but they generally don't want to you sail out of their line of sight. There's also endless bare boat charters, and crewed tourist trips. What I'm interested is none of that, but just a decent 20' to 30' sailboat I can rent for a day while my significant other cruises the jewelry shops and related things on shore.

Thanks

GJ
I'm in turks and caicos right now and just took out a Hobie cat for an hour for the first time ever. I know it's not what you have in mind. But I was just so happy to get my sailing fix today.... I was starting to get depressed.
 

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I don't think anybody is going to rent you a 20 to 30' boat to single hand for a day.
I used to have a relationship with several bareboat companies to rent a bareboat for a day, if I had a charter off the cruise ships in St. T., but as I said, we had a relationship and they knew me and my abilities.
There are beach cats in many places and I don't think they monitor where you go, but if you have no local knowledge, you would be wise to stay within rescue range should something break or you get becalmed.
 

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The Bitter End Yacht Club on Virgin Gorda in the BVI has a full range of watercraft on offer, from windsurfers and Hobie cats to IC24s (see Fleet for the complete list).

The North Sound, where the BEYC is located, is one of my favorite protected anchorages. It offers a very large area for sailing with the full trade winds but without the big Atlantic swell usually encountered in the Caribbean.
 
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