5) Kennebunkport, Maine
Cute, laid-back, and classy – Kennebunkport is the best of both worlds rolled into one fantastic coastal town. Maine is known for its rugged and rocky coastline, and Kennebunkport is no exception. There are plenty of sandy beaches too, making this small town of less than 4,000 a popular tourist destination. However, as a resident you get to enjoy four glorious seasons in this picture-perfect place. Boating, surfing, paddle boarding and swimming are popular summer activities. Dock Square is an ideal location for dining al fresco and people watching. It’s also the home of many boutique shops and art galleries. Whale-watching and foodie walking tours are other activities for residents to further appreciate what a special little town they call home. Fun Fact: The famous Walker’s Point compound is summer home to the (President) Bush family and has hosted numerous world leader guests.