Let’s be real. When you book a trip to Florida or the Caribbean in the winter, you’re picturing one thing: scorching sun, piña coladas, and sweating by the pool. You are probably packing five swimsuits, three pairs of flip-flops, and zero long sleeves. That is a rookie mistake. You'll end up in the gift shop spending $80 per sweatshirt for every member of your family! While your friends back home are shoveling snow, you will  have beautiful, warm days. But here is the catch: