I recommend bringing a dress that can double as a pool cover up, one that’s suitable for wine tasting, and a short dress for a night out on the town.
Weddings can be a tricky occasion to dress for, sometimes I even recommend wearing a jumpsuit if it’s a more vintage-inspired wedding and you want to stand out.
When traveling, you can wear more active-inspired dresses or something a bit lightweight and loose. I would wear a tennis dress or something fitness related for road trips or on a plane.