Yep, I was there in April of 2007 for 14 days. There is ALWAYS swell somewhere on the island. I stayed in a house right above Freights (super mellow, usually longboard wave). We didn't surf there much considering my biggest board was a 6'0''. We spent most of our time 5 minutes away in Southpoint (by the lighthouse). Southpoint was a bit more fun but never good in the morning. On average it was waist to head high when i was there. We also surfed Brandons a few times. This is a little bit north of Freights (when you see the old fort, you are there). Brandons was super fun. Mostly lefts with the occasional right. Every time i went there it was about shoulder high and ripable. We also drove up to Maycocks (Northwest part of island) for a day. This was the best part of my trip. even though its nearly impossible to find. It was head high and milk glass with my crew and another crew from France. Shared the waves for 6 hours that day. Had to surf Soup Bowls when we were there so we drove across the island and caught it about chest to head high and choppy.
Couple things to keep in mind.
1. Every beach i mentioned was reef break. And its really shallow. I only got wacked once at Southpoint though because of the skecthy climb out.
2. Urchins, urchins, urchins- Holy crap they are everywhere. I didnt wear boots but just walked out to knee deep and then paddled the rest.
3. Wear a tee shirt when your surfing. No matter what SPF you will burn, and burn bad.
4. when you order a rum and coke, they give you a bottle of coke, and a bottle of rum
Thanks for the reply, after reading your post I'm more inclined to find a place closer to Brandons. Originally, I located a place just above freights, but since Im traveling with multiple land anchors I going to opt for the punchier surf.