Portland Maine 5-Day Adventure Itinerary

Begin your day with breakfast at Hot Suppa, famous for its Southern-inspired dishes. Then embark on the Portland Food Walking Tour with Tastings to sample some of the best food that Portland has to offer.

Have lunch at The Honey Paw, known for its creative Asian-inspired dishes. In the afternoon, take part in the Portland Best of Maine Lighthouse Scenic Cruise to see some of Maine's most beautiful lighthouses from the water.

Enjoy dinner at Duckfat, renowned for its Belgian fries and paninis. Conclude your day with drinks at Rising Tide Brewing Company.

Start your morning with breakfast at The Green Elephant, which offers delicious vegetarian options. Then take part in the fascinating Portland Private Charter on a Vintage Lobster Boat tour.

For lunch, head over to Central Provisions for small plates that pack big flavors. Spend your afternoon visiting New England Distilling for a tour and tasting session.

Dine at Street & Co., known for its seafood dishes prepared in Mediterranean style. End your evening by exploring Old Port's vibrant nightlife or enjoying live music.

Kick off your day with breakfast at J's Oyster, where you can enjoy fresh seafood right by the water. Then join the Portland Guided Bike Tour Around The Peninsula to see more of Portland's scenic spots.

Have lunch at Petite Jacqueline which offers French bistro classics in a cozy setting. In the afternoon take part in an exciting activity:  Portland Schooner Tall Ship Cruise on Casco Bay. Enjoy sailing around Casco Bay on this historic vessel.

End your day with dinner at  DiMillo's On The Water. This floating restaurant offers stunning views along with delicious seafood dishes.

Start your final day with a delightful breakfast at Becky's Diner, known for its hearty and classic American breakfast options. Afterward, take a serene walk along the Eastern Promenade, where you can enjoy beautiful views of Casco Bay and the surrounding areas.

For lunch, head to Portland Lobster Company to savor some of the freshest lobster rolls in town. In the afternoon, embark on the Portland Best of Maine Lighthouse Scenic Cruise to witness some of Maine's most iconic lighthouses from the water.

Conclude your trip with a memorable dinner at Scales, renowned for its seafood dishes and waterfront views. End your evening with a leisurely stroll through Old Port, soaking in the vibrant atmosphere and reflecting on your wonderful trip.