Start your trip by flying into Portland International Jetport. Check hotel and flight prices here. After checking in at your hotel, spend the morning exploring the Old Port district. Wander through the cobblestone streets, browse the boutique shops, and grab a delicious brunch at one of the charming cafes. In the afternoon, head to the Portland Head Light, located in Fort Williams Park. This iconic lighthouse offers breathtaking ocean views and a glimpse into Maine's maritime history. In the evening, enjoy a seafood feast at one of the many renowned waterfront restaurants.
Start your day with a visit to the Portland Museum of Art. This world-class museum houses a diverse collection of artworks, including pieces by Winslow Homer and Andrew Wyeth. Spend the morning soaking in the beauty of the exhibits. In the afternoon, explore the Victoria Mansion, a stunning example of pre-Civil War architecture. Take a guided tour to learn about the mansion's history and marvel at the intricate details. In the evening, attend a performance at the State Theatre, a historic venue known for hosting a variety of live shows.
Embark on an outdoor adventure by visiting Casco Bay Islands. Take a ferry to Peaks Island and spend the morning exploring its picturesque landscapes, charming neighborhoods, and local art galleries. Rent a bike to leisurely ride around the island. In the afternoon, head to Eastern Promenade Park, a waterfront park offering stunning views of the city skyline. Take a leisurely stroll along the Eastern Prom Trail or have a picnic in the park. In the evening, enjoy a sunset cruise on Casco Bay to admire the scenic beauty of the surrounding islands.
On your final day, take a day trip to the charming coastal town of Kennebunkport. Start your morning by exploring Dock Square, the heart of the town, with its quaint boutiques, art galleries, and seafood restaurants. Visit the stunning St. Ann's Episcopal Church, situated on a rocky promontory overlooking the ocean. In the afternoon, take a scenic drive along Ocean Avenue to admire the magnificent coastal mansions. Stop by Walker's Point, the summer residence of the Bush family. End your day with a relaxing beach walk along Gooch's Beach.
When in Portland, make sure to visit the Portland Observatory. This historic tower offers panoramic views of the city and harbor. Another hidden gem is the Allagash Brewing Company, where you can take a tour and sample their renowned Belgian-style beers. Locals also love exploring the Portland Trails, a network of scenic walking and biking paths that connect various parks and neighborhoods. Lastly, don't miss out on visiting the Holy Donut for their famous potato donuts made with local ingredients.