Vancouver, British Columbia
When the rest of the nation is zipping up their winter parkas and scraping the frost off their windshields, Vancouverites can be found strolling casually along the Sea Wall, eating lunch on a sunny patio, or even playing a round of golf (seriously - there are golf courses that are open year-round).
In January, Vancouver has daily highs of 6.9 degrees Celsius (44 degrees Fahrenheit) and lows of 1.4 degrees Celsius (34.5 degrees Fahrenheit). Although it's not in Florida or Hawaii, the weather is warm enough to make being outside enjoyable. Additionally, it's not unusual for Vancouver people to enjoy a few extra warm and sunny days in the middle of winter; it's like getting a bonus sneak peek of spring. While snow is unlikely to fall in Vancouver at any time of year, the chances are good that you'll see some of that infamous Vancouver rain if you go there in the winter. If it starts to rain, bring an umbrella or a raincoat, but don't let that stop you from seeing the city.