Start with coffee and breakfast sandwiches or pastries at a popular local café; they typically open early (around 7:00AM) and are a reliable on-the-go start.
Short visit to Maymont’s park and historic estate—grounds are open until about 5:00–6:00PM depending on season, so allow a quick stroll for sunset views.
Modern Israeli tasting-style dinner—Zahav is a top local destination (open for dinner evening hours, closed some weekdays—Sept 19 is a Thursday so it should be open); reservations strongly recommended.
Short 30–45 minute drive to Newport to walk the Cliff Walk and tour The Breakers; Cliff Walk is always open (outdoor), The Breakers mansion tours are typically open 10:00AM–5:00PM in September.
Head north on US-1 / I-95 for a scenic coastal stretch; plan for approximately 3.5–4.0 hours driving plus short stops in coastal New Hampshire if desired.
Take a short ferry cruise to one of the nearby islands (check ferry schedules) or visit a local brewery for a tasting; ferries often run afternoon schedules in September.
Farm-to-table and wood-fired cooking in a popular Portland restaurant—book ahead; dinner service continues into the evening and is a great finale to the trip.