Fast answer
For a first Locorotondo evening, keep the plan compact: use Via Nardelli and the belvedere before dinner, stay in the old town when you want the simplest walk-back, and treat San Rocco or other event nights as live checks. Countryside and masseria dinners belong to car-led stays with booking, route, and return transport confirmed. Local wine belongs as context, not as a producer shortlist.
If you only do one thing
Default to a view walk on Via Nardelli, then an old-town dinner plan that you confirm the same day for venue, hours, table, and event pressure. If you are sleeping in the contrade, decide the dinner, driver, taxi, or return route before leaving the property.