Re: Hotel in/near Charlotte Amalie
You didn't mention price point or amenities. If you are interested in local color, there are a number of smaller hotels/B&Bs in and around Charlotte Amalie. We're not talking about the Ritz and there is always the risk of an ever-changing scene from year to year, but you might check out the Green Iguana by Bluebeard's Castle or Hotel 1829. We've stayed at these places, as well as the nearby Galleon, which had a good breakfast a few years ago, but the cleanliness of the room was not up to our liking. The Green Iguana is at the top end of the 99 steps, so you may want a taxi there if you aren't up the the climb. These places are all walking distance to the waterfront. It's been a few years since we've stayed at these places--maybe 2 years for the Green Iguana and more for the others.
Another interesting B&B is the Island View, but it's outside the downtown area and you'll need a taxi to get to and from dinner. We stayed there last year and would go back.