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St. Barth's & Anguilla - too "STUFFY"?

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I’m not well off but I found some fair deals to Anguilla (CuisinArt Spa) and St. Barths (Sofitel Hotel Christopher) but worry that although they are both splendid islands, that there are no reasonably priced restaurants, etc. and that I would feel somewhat out of place. How are the people who frequent this island? Down to earth or a bunch of rich, pretentious, high-falutin people? I don’t want to feel like I need to leave the hotel in search for a reasonably priced meal because I don’t want to spend $90 on room service for a basic dinner for two. I want to enjoy my vacation so I don’t want to “think twice” at what the price of everything is (like a drink at poolside).

Also, how are the driving conditions in both islands? I’d rather not pay so much for a taxi (I heard at least $15 each way in Anguilla). I heard the roads are “hilly” at St. Barths.

Anyone been to those two hotels and have feedback?

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