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Travel companion with special dietary needs

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I'd like to plan an island getaway for my Mom's 80th birthday in the fall of 2013, along with my sister. My challenge is to find a place where I can work with my sister's dietary restrictions. She doesn't eat in restaurants typically because she must have food specially prepared without oil and fat. Lately she's eating a vegetarian diet, which makes it even more challenging. Does anyone have experience with a resort where they will make special meals for people? In my experience Disney hotels, for example, are very good about this. A condo with our own meals to cook is an option, but I think Mom would prefer to be served on this occasion.

Mom is not very active, so beaches and water sports are less important. Historic sites, good music/entertainment, short excursions, and excellent service probably suit Mom's needs best. I appreciate any suggestions you have that I can explore.

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