Morning: Arrive at the Residence Inn Portland Downtown and get settled into your room. Take some time to relax and unpack.
Afternoon: Enjoy a leisurely stroll along the Old Port District with its charming cobblestone streets and browse unique shops and boutiques. Stop by a café for a light snack.
Evening: Dine at Fore Street, a renowned restaurant offering fresh local seafood and cozy ambiance. Take a gentle walk by the nearby waterfront afterward.
Find HotelsMorning: Take a scenic drive down to Higgins Beach (about 20 minutes from downtown). Enjoy a calm beach morning with soft sand and gentle waves.
Afternoon: Head a bit further south to explore the quaint town of Old Orchard Beach. Take it slow with some beachside shopping and a casual lunch overlooking the ocean.
Evening: Return to Portland for an early dinner at Eventide Oyster Co. followed by relaxing views of the sunset from the Portland waterfront.
Find HotelsMorning: Take a ferry ride from Portland to Cushing Island. Enjoy a peaceful walk on the island’s nature trails and quiet beaches, ideal for relaxing but gentle movement.
Afternoon: Have a packed picnic on the island or return to Portland and grab lunch at a harbor-view restaurant. Spend some time browsing local shops.
Evening: Embark on a Casco Bay Sunset Cruise, a relaxing way to see the islands and coastline as the sun sets.
Find HotelsMorning: Drive about 40 minutes to Kennebunkport. Wander the charming downtown shops, galleries (window shopping), and cafes.
Afternoon: Relax at Goose Rocks Beach, a serene spot for beachcombing and soaking in ocean views.
Evening: Enjoy dinner at The Boathouse Waterfront Hotel’s Shore Road Restaurant for fresh seafood with a waterfront view, then return to Portland.
Find HotelsMorning: Start with brunch at Central Provisions, a popular spot for creative comfort food. Then slowly explore the Portland Farmers Market if open, or relax at the hotel pool or lounge.
Afternoon: Take a gentle stroll or rent a kayak from Portland Paddle to paddle around the calm waters of Casco Bay—easy and low impact water activity.
Evening: Light dinner at Duckfat known for casual dining with Maine flair. End the night with a quiet walk at the Eastern Promenade park watching the harbor.
Find HotelsMorning: Drive 30 minutes to Freeport, home to the famous L.L.Bean flagship store and many outlet shops. Browse at your leisure.
Afternoon: Enjoy lunch at a local café such as Harraseeket Lunch and Lobster Company, then stop by the Wolfe’s Neck Woods State Park visitor area for scenic views without hiking.
Evening: Return to Portland and dine at Street & Co. for Mediterranean-inspired seafood in a cozy setting.
Find HotelsMorning: Enjoy a relaxed breakfast at Hot Suppa, known for classic southern-inspired dishes. Take a last walk along the waterfront or visit any favorite local shop for souvenirs.
Afternoon & Evening: Prepare for departure and safe travels!
Find HotelsTotal Estimated Cost: $1,280
If you want to extend your trip, consider adding a gentle day trip to nearby Boothbay Harbor for coastal views and lighthouse sightseeing via a leisurely ferry ride. For reducing your trip duration, focus on just Portland and nearby beaches, skipping further day trips to keep the pace slow and minimize driving time.