Since we own a place on St. Thomas, I don't really have first hand experience on places to stay. My family has stayed at Windward Passage before and it served its purpose of being a place to stay prior to taking the ferry the next morning. I have read about people saying not to go out at night from there and personally, I think that is a bit dramatic but I would definitely be cautious at night. Regardless, this doesn't sound like what you are looking for. My condo is in the Bolongo Bay area so I am very familiar with Bolongo Bay Resort, as we walk down there a lot for food and drinks. It is an older hotel but seems to be clean and taken care of...it is not the Ritz though. The beach is OK. It is a bit rocky in spots and not the perfect white sand beach you dream of but the views are great. It has a nice pool that overlooks the bay and we have always been happy with the food there at Iggie's. There is also another restaurant at the opposite end of the beach called Mim's that has amazing food. They are known for their curry lobster, among other things. Bolongo is on the southeast side of the island so you are looking at about a 20 minute cab ride, which is not as far as Red Hook or Sapphire but certainly further than Emerald Beach. If it were me, I would just stay at Emerald Beach. It is close to the ferry and airport, has a great beach and a restaurant on site. I know people who have stayed there and thought it was just fine.