A career-driven couple looks to make the leap from Greenwich, Connecticut, to their island fantasy destination of East Hampton, N.Y., where they can finally enjoy the fruits of their labour.

A woman dreams of owning an island home on Martha's Vineyard since childhood, and her husband jumps on board when he visits the island and falls in love with the laid-back vibe and outdoor activities.

A Boston accountant wants to escape city life by finding a beach getaway on Aquidneck Island. He seeks a bachelor pad near the water and downtown Newport.

A couple that has spent most of their lives teaching on boats is ready to put down roots on dry land with their two kids, and hope to find a turn-key home on Aquidneck Island in Narragansett Bay that has a large yard close to the beach.

After spending many summers on the island, a couples sets out to make their dream come true and find a forever home on Nantucket.

Tired of their boring lifestyle in rural Ohio, a couple is ready to liven things up at their favourite childhood vacation spot of Indian Lake. They want a large turnkey home for their extended family as well as a dock on the open water.