After collecting your rental car, head to Burlington Waterfront Park for an easy first look at the city and Lake Champlain. The drive from Burlington International Airport is about 10–15 minutes; downtown parking is generally metered or paid, so check the posted limits and consider using a garage rather than moving the car repeatedly. Allow about an hour to stroll the shoreline, watch the boats, and take in the Adirondack views—late afternoon is especially pleasant here, though the waterfront can be breezy even in summer.
Continue along the waterfront to ECHO, Leahy Center for Lake Champlain, only a few minutes away on foot or by car. Plan roughly 1½ hours for the hands-on exhibits about the lake, local wildlife, and regional ecology. Check the museum’s current closing time and admission prices before arrival, since hours can vary seasonally; if you park once downtown, walking is simpler than dealing with another space.
From the waterfront, walk uphill toward Church Street Marketplace, Burlington’s lively pedestrian center, in about 10–15 minutes. Spend the next hour or so browsing the independent shops and street-level cafés, then stop at Lake Champlain Chocolates for Vermont-made truffles, chocolate bars, or a café treat to take along for the road. This is a good time to wander without a strict agenda—Church Street is compact, and the best parts are often the side streets and small storefronts just off the main promenade.
For dinner, make your way to Hen of the Wood, ideally with a reservation; it is a polished, seasonal restaurant where the menu follows Vermont farms and nearby producers. Budget about $60–100 per person before drinks, and allow two hours for a relaxed meal. It is walkable from Church Street, though a short ride or your parked car may be more comfortable if you have luggage; after dinner, keep the evening gentle, since tomorrow’s drive to Portland is best started early.
Leave Burlington around 7:30 AM for the drive to Portland, allowing roughly 4½–5 hours plus a fuel and coffee stop. The practical route follows U.S. Route 2 east before joining I-93 and I-95 south; traffic is usually manageable, though August construction and Boston-area congestion can add time. Once in Portland, leave the car at your hotel or use a downtown garage rather than trying to street-park all afternoon. Plan on approximately $45–70 for fuel and parking.
After settling in, drive about 15 minutes to Portland Head Light in Fort Williams Park in nearby Cape Elizabeth. The lighthouse itself is viewed from the grounds, with excellent rocky-shore paths and Casco Bay outlooks; allow about 1½ hours. The park is open from sunrise to sunset, and parking is paid seasonally—roughly $5–10 depending on the day—so comfortable shoes are worthwhile. Return to Portland and spend the late afternoon wandering the Old Port, where cobbled lanes around Commercial Street and Fore Street mix brick warehouses, independent shops, galleries, and working waterfront views. It is compact and best explored on foot; allow about 1½ hours.
Have an early dinner at Eventide Oyster Co. in the Old Port, ideally arriving before the busiest dinner period or joining the waitlist online. The menu centers on Maine oysters, lobster dishes, and other seafood, with a realistic budget of $35–60 per person before drinks. Afterward, drive or walk east toward the Eastern Promenade—about 10 minutes by car from the Old Port, or roughly 25 minutes on foot—and finish with an easy waterfront stroll overlooking Casco Bay. Sunset is especially pleasant from the grassy slopes near the promenade; bring a light layer, since the ocean breeze can feel cool even in August.