Sunny All The Time, Open 24 Hours

With a yearly temperature low of 72 degrees, it's always a great time to plan a Virgin Island vacation. As for prices, the Virgin Island prices are relatively low all year round. For a decent accommodation, one can expect to pay about $125 USD per evening. Flights, too, are often cheap—especially if you plan in advance. Known as a sailing touchstone of the world, you can plan to catch a sailing race or activity while you are there, with sailing regattas happening on the Virgin Island at least once per month.