"Winter" in Charleston is a strange mix of freezing cold days and gorgeous sunny, but brisk, afternoons. Luckily though most days are quite beautiful and the outdoors begs to be explored. With a jacket.
Sullivan's Island is a short ways outside of the city of Charleston and one of my favorite beaches. Plus you can take a puppy or two and let them frolic about in the water. And use you as a towel later :) It also has a main strip of delicious restaurants a quick walk from the beach that are perfect for brunch, or a post-beaching beer. Most even allow dogs on their porches. My personal favorite for those types of days is Cafe Medley which serves casual quality food. For a spectacular date night Obstinate Daughter provided a lovely atmosphere, great food, and excellent service. Plus seeing the winter sun set from their second story restaurant was a treat.
One of the most exciting new shops in town is Candlefish. It's a great store from the makers of Produce and Rewined, but my favorite part is their Workshop in the back that they open up to guests. I attended a candle-making (of course) class and had a great time with friends (and wine!). They've also recently started partnering with local artisans and I went to a soap-making class with Old Whaling Company. I love smelling that soap so much I might never use it. LOL!
An especially striking aspect of Charleston is the loyalty between local artists, artisans, and farmers. Many restaurants will list right down to the specific location where all of their fresh ingredients come from and do so with great pride. Like Candlefish, local businesses are always on the lookout for how to support each other. Even in the dead cold of winter it's always cozy in Charleston <3