Pick up your reserved mid-size SUV or sedan for the trip; confirm one-way drop-off at Portland (PWM) and that insurance/roadside assistance are added. Expect counter service at airport desks from early morning.
Stroll the waterfront promenade and colorful historic homes to soak up Charleston's architecture and lowcountry atmosphere; outdoor self-guided exploring is available anytime.
Take the ferry tour to Fort Sumter to learn about the Civil War’s opening shots — ferries run several times daily; check the National Park Service/ferry schedule and arrive early for boarding.
Classic seafood and Southern dishes in a historic waterfront setting — a relaxed first-night dinner option; confirm dinner hours and reserve if possible.
Walk the scenic Riverwalk and, if time permits, tour the USS North Carolina (battleship tours often open around 9–10am) to learn naval history; check ship/tour hours in advance.
Continue north via I-95/I-85 towards Richmond; this longer drive is roughly 4.5–5.5 hours depending on traffic — schedule a couple of short rest stops.
Head north on I-95 through Connecticut and Massachusetts toward Maine; expect roughly 5.5–6 hours of driving with a planned coffee/stretch stop midway.
Drive the Park Loop Road, stop at scenic overlooks and visit Cadillac Mountain for sweeping coastal vistas; the park is open year-round, but check seasonal visitor center hours.
Evening commercial flight back toward South Carolina (may require a connection); book a flight that departs after car drop-off and airport check-in (allow 1.5–2 hours before departure).