If you are looking for a creative and fun Virgin Island vacation, you may want to consider one of the many resorts that can help you enjoy the island both by land and by water. There are hotels that will let you stay on island and then take a boat to explore. There are yachts to be chartered or boats to be had for day sails.
If you really want to take a sailor's vacation, you should look for local sailing lessons in your area so you can learn your aft from your stern. Many lakes, rivers and ocean communities offer sailing lessons at reasonable rates. Learn the craft and enjoy!