Yes, you need to make a car reservation ahead of time. You can try the TTOL sponsors list. Most of them are still in business, although some you may need to call, as opposed to reserving by email.

For Italian in Simpson Bay, the most popular place is probably Izi, although there is also Sal & Peppe and Isola. Isola is at Simpson Bay Resort. At SBR is also Le Patrona, which is Mexican (as in the COUNTRY, not Tex Mex). I enjoyed our meal there, but some others have not liked it. Don't go, if you're looking for Tex Mex. For seafood, the best place WAS Skipjacks, but I don't think they have reopened since the hurricane, although they were working on it.

For beaches, suggest you go to Mullet, which is a BEAUTIFUL beach, but can be crowded. Toilet is a porta potty. Rosie's there serves great ribs and chicken. Chairs and umbrellas for rent, and you can take a cooler there with you if you like. Also you might try Karakter, which is in Simpson Bay, more upscale eats, free chairs and umbrellas when you eat. As a result, do NOT take your own cooler there. Orient Beach is stunningly beautiful now, but almost no services. If you like a beautiful deserted beach, Orient would be your best bet. Bring your own cooler, umbrella, blanket, whatever, for a spectacular day on a mostly deserted beach. There are only a couple of places to eat on Orient now, down close to, and at, Club Orient, or what remains of it.

If you have any other questions, please post!