Like a good wine, the chic-est clothes only get better with time, and there is plenty of chic at Second Skin. Uncluttered and easygoing, the folks here rack up 1950s swim trunks beside flowy pastel chiffon blouses and Art Deco costume jewelry.

Old Books is pretty self-explanatory. This Front Street bookshop not only offers beautifully bound first editions and addictive beach reads, they also organize literary history walking tours. Stop in on a Sunday and browse to the sound of local piano player James Jarvis.

You know it’s true—guys almost always give a better manicure. Guys Do Nails owner Dynh Le has transformed his historic Princess Street storefront into a hip, vintage-y manicure mecca where comfy oversized leather pedicure chairs sit behind hammered copper foot baths.