The Gaff is one of those only-in-Port-A spots where the line between indoors and outdoors blurs in the best possible way — open air, cold drinks, and Jim Dugan bringing live music to a crowd that came for a good night and stayed for another round. While you're there, the pizza alone is worth the trip, though the parrot bites have their own devoted following.
After the music fades and the night wraps up, Beached Inn is just a short walk away — the kind of place where a sunset from the porch and the sound of the surf make the perfect end to an evening out.