Parking in town is usually better when there are no ships in town. Most people try to park in the Ft Christian parking lot across from the court house, but it frequently fills up during the week by 10:00 a.m. You can usually find parking close to the Holiday Inn Windward Passage - there are several lots in the area. Some people park at Havensight, do a little shopping there (Gourmet Gallery, Dockside Books, etc), and then take a taxi to town.

Red Hook is just as bad or worse. The shopping area where Chelsea Drugs and Subway are located usually has some parking in the back - again, you should shop there if you're going to use their parking. Other than that, it's whatever you can find along the road. There's a parking lot beneath American Yacht Harbor, but I don't know the rates/details about parking there. Many people find parking at the mall, and take a local safari to Red Hook and back.

Parking beneath American Yacht Harbor is free, there is also a parking lot at street level, we've never had a real problem finding a spot you may need to circle a couple of times.

If you want to pack at Fort Christian, get there early for parking spot, last year we gat the around 11-11:30 and the lot was full.

We never had a problem parking thank god.

As far as Red Hook, we ALWAYS got a parking space in the underground parking lot across from Duffy's.

In Charlotte Amalie, we go there about 9 and walked around a bit, so we didn't have a problem parking in front of one of the stores. Also you could park at the Havensite Mall and walk all over town. It's not that bad.