Morning: Arrive at the Residence Inn Portland Downtown and settle in. Take some time to relax and freshen up.
Afternoon: Enjoy a leisurely stroll along the Old Port district, exploring quaint cobblestone streets filled with unique boutiques and artisan shops.
Evening: Dine at Eventide Oyster Co. for fresh seafood in a cozy atmosphere near the waterfront.
Find HotelsMorning: Take a relaxing Casco Bay ferry ride to one of the nearby islands like Great Diamond Island or Peaks Island with beautiful waterfront views and light walking.
Afternoon: Have lunch at a waterfront café on the island and enjoy some light shopping at charming local stores.
Evening: Return to Portland and unwind with a sunset cruise around Casco Bay, taking in the stunning coastal skyline as the sun sets.
Find HotelsMorning: Head south to Two Lights State Park and nearby Ogunquit Beach for some peaceful beach time and gentle ocean breezes.
Afternoon: Have a leisurely lunch at Clam Shack in Ogunquit, known for its classic Maine lobster rolls and seafood.
Evening: Enjoy a scenic drive along the Ocean Avenue in Perkins Cove, stopping for an early dinner or dessert by the harbor before heading back to Portland.
Find HotelsMorning: Visit the Portland Museum of Art to enjoy impressive collections without strenuous activity.
Afternoon: Explore Munjoy Hill area with its charming cafes and unique shops. Stop by the Portland Head Light for iconic views and photo opportunities.
Evening: Dinner at Fore Street Restaurant featuring locally sourced ingredients in a warm ambiance.
Find HotelsMorning: Leisurely morning strolling through the Commercial Street Waterfront and visiting artisanal shops and galleries.
Afternoon: Join a gentle kayak or paddleboard rental from a local outfitter to explore calm waters around Portland Harbor.
Evening: Casual dinner at Duckfat, famous for their fries and cozy atmosphere.
Find HotelsMorning: Drive to Spring Point Ledge Lighthouse in South Portland for peaceful waterfront views and easy walking.
Afternoon: Lunch at Harbor Fish Market & Grille with fresh seafood and harbor vistas.
Evening: Take a quiet evening boat tour of Casco Bay focused on relaxation and picturesque views.
Find HotelsMorning: Enjoy a slow breakfast at Becky’s Diner, a Portland classic.
Afternoon: A final stroll along the waterfront or a visit to Deering Oaks Park before packing up.
Evening: Depart from Portland feeling relaxed and refreshed.
Find HotelsTotal Estimated Cost: $690 (for two people)
If you wish to extend your trip, consider adding an overnight stay on one of Casco Bay’s quieter islands like Peaks Island to experience local charm and seaside relaxation. For a shorter trip, focus on Portland’s Old Port, waterfront activities, and one scenic ferry or sunset cruise to maximize relaxation without extensive travel.