The Eastern Promenade stretches along the eastern edge of the Portland peninsula, overlooking Casco Bay. It is easily accessible from downtown Portland and is a popular destination for locals and visitors alike. The park features a picturesque waterfront promenade that runs parallel to the shoreline, offering unobstructed views of the bay and its islands. Visitors can enjoy panoramic vistas of sailboats, fishing boats, and ferries navigating the waters, as well as views of nearby lighthouses and coastal landmarks.

The Portland Observatory is situated on Munjoy Hill, providing panoramic views of Portland Harbor, Casco Bay, and the surrounding coastline. The hillside location offers a strategic vantage point for observing maritime activities and signaling incoming ships. Built in 1807 by Captain Lemuel Moody, the Portland Observatory is the only known remaining maritime signal tower in the United States. It was constructed as a private enterprise to provide a communication system for merchants and shipowners to track approaching vessels and facilitate trade in Portland's busy harbor.

Similar to the Eastern Promenade, the Western Promenade offers stunning views of Casco Bay, with vistas of islands, sailboats, and coastal landscapes. The park's elevated position provides sweeping views of the surrounding area, making it a popular spot for sightseeing and photography. The Western Promenade is home to several historic landmarks and monuments, including the Western Cemetery, a historic burial ground dating back to the early 19th century. Visitors can explore the cemetery's picturesque grounds and learn about Portland's history through its gravestones and memorials. It is also home to historic mansions formally occupied by Portland's elite.

Situated on the rocky coastline of Cape Elizabeth, Portland Head Light overlooks Casco Bay and the Atlantic Ocean. The lighthouse is part of Fort Williams Park, which offers stunning views of the surrounding coastline and nearby islands. Portland Head Light has a rich history dating back to 1791 when it was commissioned by George Washington and became Maine's oldest lighthouse. The original keeper's quarters still stand nearby, offering insights into the life of a lighthouse keeper during the 19th and early 20th centuries.

One of the 3 lighthouses you can see in South Portland.

Once called the "most photographed house in the state" of Maine, the Wedding Cake House, known formally as the George W. Bourne House. George was a prominent ship builder and businessman that had grown up in the house next door which is now the Waldo Emerson Inn. His father built the federal brick house as a wedding present for George and his new bride Jane in 1825. The “icing” was added 26 years later starting in 1852 after a fire destroyed the barn.

Walker's Point is situated along the rocky coastline of Kennebunkport, approximately 4 miles southeast of Dock Square and the town center. The property encompasses a scenic stretch of shoreline overlooking the Atlantic Ocean. Walker's Point is a private estate owned by the Bush family. The main residence, known as the Bush Compound, includes a seaside mansion that has served as a summer retreat for generations of the Bush family. The compound features stunning views of the ocean and surrounding landscapes.

Take a short scenic drive along the beaches and then further up along the fabulous rocky coast leading to Walker's Point along Ocean Ave.

Dock Square is situated in the heart of Kennebunkport's downtown area, near the Kennebunk River where it meets the Atlantic Ocean. The square is a focal point of the town's bustling waterfront district and is easily accessible by foot from nearby attractions and accommodations. The square offers scenic views of the Kennebunk River and the bustling harbor, where lobster boats and sailboats can often be seen coming and going. Visitors can stroll along the waterfront boardwalk or relax on benches to take in the maritime scenery and watch the activity on the water.