Morning: Land at Portland International Jetport, check into a boutique hotel on the waterfront, and enjoy a sunrise walk along the Eastern Promenade with sweeping views of Casco Bay.
Afternoon: Meander through the cobblestone streets of the Old Port, sampling lobster rolls at a harbor‑side shack and browsing art galleries and artisan boutiques.
Evening: Dine at a farm‑to‑table restaurant in the Old Port, then drive to Portland Head Light at Cape Elizabeth to watch the sun dip behind the Atlantic.
Find HotelsMorning: Board the Casco Bay Ferry for a scenic island hop, stopping at Peaks Island for a bike ride and coffee by the shore.
Afternoon: Return to Portland and head south to Ogunquit Beach, strolling the famous Marginal Way trail that hugs dramatic cliffs.
Evening: Savor fresh clams at a waterfront eatery in Ogunquit, then catch a sunset from the historic Perkins Cove.
Find HotelsMorning: Drive to Kennebunkport, exploring the charming Dock Square and the scenic Walker’s Point garden (the Kennedy family summer home).
Afternoon: Continue to Kittery for a leisurely walk along the Kittery Point lighthouse and a taste of the famous Kittery Seafood Shanty.
Evening: Return to Kennebunkport for dinner at a seaside bistro, then enjoy a quiet night stroll along the moonlit Brandy Cove.
Find HotelsMorning: Travel north to the iconic Pemaquid Point Light, climbing its granite tower for panoramic ocean vistas.
Afternoon: Head to Rockland to visit the Farnsworth Art Museum and browse the bustling harbor’s craft shops.
Evening: Dine on locally caught fish at a harbor‑front restaurant, then catch a sunset from the rocky bluff at Rockland Breakwater.
Find HotelsMorning: Arrive in Camden and take a leisurely walk along the historic Camden Harbor, watching the sailboats sway in the breeze.
Afternoon: Ride the scenic Mount Battie Auto Road to the summit for breathtaking 360° views of Penobscot Bay and the surrounding mountains.
Evening: Enjoy a farm‑to‑table dinner in downtown Camden, then linger on the waterfront to admire the lights reflecting on the water.
Find HotelsMorning: Enter Acadia National Park via the Park Loop Road, stopping at Jordan Pond for a short hike around its crystal‑clear waters.
Afternoon: Drive up to Cadillac Mountain for the classic “first sunrise” view, then explore the historic carriage roads by bike.
Evening: Descend into Bar Harbor, savoring a lobster dinner on Main Street before a leisurely stroll along the waterfront promenade.
Find HotelsMorning: Take a relaxed walk on the Sand Beach within Acadia, feeling the soft sand and listening to the surf.
Afternoon: Enjoy a final lobster roll at a local market, then head south on the scenic route back toward Portland, stopping at any missed viewpoint.
Evening: Return the rental car at Portland International Jetport and depart, carrying memories of rugged cliffs, historic lighthouses, and charming coastal towns.
Find HotelsTotal Estimated Cost per person: $638
If you have extra time, add a day in Bar Harbor to explore the quieter western side of Acadia or take a whale‑watching tour from Portland. To shorten the trip, combine Day 4 and Day 5 by staying in Rockland and using it as a base for both the Pemaquid and Camden areas, which reduces driving time while still hitting the highlights.