I would not sail the windward side. I enjoyed Montserrat a lot. There is not a lot there - most was destroyed by the volcano. As far as I know there is only one place to drop anchor and check in - Little Bay. Be careful as shipping traffic comes in night and day. Even though there is no "channel" make sure they have a clear path to the dock. Most of the island is in the volcano exclusion zone. Roads are very narrow but it is possible to rent a car at the airport and drive around. Expect that if you get close to shore you are going to be sailing through clouds of ash.