5-day trip to Portland, Maine Itinerary

Start your day with a scenic drive to Cape Elizabeth and visit the iconic Portland Head Light, one of the most photographed lighthouses in the United States. Enjoy a delicious brunch at Salt & Straw while taking in the breathtaking ocean views.

Explore the picturesque town of Freeport and indulge in some retail therapy at the famous L.L.Bean Flagship Store and other outlet shops. For lunch, savor the flavors of Maine at Harraseeket Lunch & Lobster Company, known for its fresh seafood.

Return to Portland and experience a memorable dinner at Ox Restaurant, known for its exceptional farm-to-table cuisine. Afterward, enjoy a nightcap at Departure Restaurant + Lounge, a rooftop bar offering panoramic views of the city.

Embark on a scenic drive to explore the natural beauty of the region. Visit the stunning Multnomah Falls and hike through the lush trails of Oneonta Gorge. For a quick snack, stop by Pine State Biscuits for their famous biscuits.

Discover the enchanting Columbia River Gorge and enjoy a picnic lunch amidst the breathtaking scenery. Afterward, indulge in a wine tasting experience at Willamette Valley, known for its world-class wineries.

Return to Portland and treat yourself to a delightful dinner at Andina Restaurant, offering a fusion of Peruvian and Latin American flavors. End the day with a visit to Voodoo Doughnut for their unique and delicious doughnut creations.

Start your day with a guided tour of the Portland Underground Shanghai Tunnel Tour with Beer Tasting, where you'll learn about the city's intriguing history. Grab a quick bite at Screen Door for their famous Southern-style brunch.

Explore the historic Pittock Mansion and enjoy panoramic views of the city. For lunch, head to Lardo and indulge in their mouthwatering sandwiches. In the afternoon, take a leisurely stroll through the Portland Japanese Garden and immerse yourself in the tranquility of nature.

Embark on a thrilling Portland Ghosts, Poltergeists, and Psychopaths Walking Tour to uncover the city's haunted past. Afterward, enjoy a spooky-themed dinner at Sweedeedee, known for its comforting and delicious dishes.

Start your day with a scenic bike ride along the Portland Steel Bridge and explore the charming neighborhoods of Portland. Enjoy a delightful breakfast at Blue Star Donuts, known for their gourmet donut creations.

Discover the city's vibrant food scene with the Portland All-Inclusive Walking Food Tour, where you'll sample a variety of local culinary delights. For a refreshing drink, visit Pok Pok and try their signature Thai-inspired cocktails.

End your trip with a memorable dinner at Nong's Khao Man Gai, known for its authentic Thai cuisine. Afterward, embark on the Portland Ghosts Boos and Booze Haunted Pub Crawl to experience the city's haunted pubs and enjoy a few drinks along the way.