Last trip we were in Grand Case on Sunday. We had dinner at Calmos Café. Great food, live music and feet in the sand.
For the SB, I would open another thread and ask that question. Somebody will have an answer.
I would talk to your charter co. about mooring at SBH. Our problem was we had to go so far out to find good spacing that we were closer to Gros Ilets than the harbor. We only showered and slept on the boat so it wasn't a big deal.
On SBH I would rent cars and explore the island. driving there is an experience.
For dining on Anguilla we had a fantastic meal at Sandbar in Sandy Ground (Road Bay). Its a tapas place run by a couple from San Francisco. It was outstanding.
Our dinner at DaVida on Crocus Bay was wonderful, too.
In SBH, Eddies is fantastic. You have to have a burger at Le Select. We spent a great day on the beach with lunch at
La Case De Isle/Cheval Blanc. I understand that Shellona (used to be Do Brazil) is supposed to be good, too.
Others that have been good to us are Maya's, Le Repaire, and La Gloriette is a low key lunch spot on the other side of the island.