I'm going to start giving you some of my opinions on the restaurants and bars in Anguilla (because I know how much you all value my opinion). We'll start with the places that are on the agenda, and then I can give you some thoughts on some additional places that you might want to hit if you have some free time, or are staying extra days.
We described The Pumphouse briefly below, but here is a little more detail in case that and its website wasn't enough for you. The Pumphouse is in Sandy Ground, on the side of the road that borders the big salt pond, which you can see on the right in the photo at the top of the page. It's an old pumphouse (imagine that!) that would pump the salt out of the pond to eventually sell. Salt production and exportation used to be Anguilla's primary commercial activity prior to the advent of tourism there about 25 years ago.
It's a fun bar with a pretty good menu of bar food, including some good local stuff. They frequently have live music, including Musical Brothers on Thursday nights. We'll be there that night, and you'll get to enjoy their fine reggae stylings, and a mix of original songs and covers (both reggae and other songs you know that they've made into reggae). It's always a fun crowd, and seems to be an even mix of locals and visitors. Some people have been coming to the island for years and always go back there. Some are there for the first time. We have frequently run into people there that we've met on the island, including hotel employees and just random people that seem to be everywhere. And everyone hangs out and has fun together.
It gets crowded, but not super-crowded, and it's never too hard to get up to the bar to get a drink. It's kind of a wooden shack with a concrete floor, some high and low tables, and the bar is on the left when you walk in. The band plays in the back, where some of the pumphouse equipment still sits. Very informal place - as Korinne noted below - wear comfortable shoes!
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