Stiles Island is a wealthy and exclusive enclave separated by a bridge from the Massachusetts coast town of Paradise. James Macklin sees the island as the ultimate investment opportunity: all he needs to do is invade it, blow the bridge, and loot the island. To realize his scheme, Macklin, along with his devoted girlfriend, Faye, assembles a crew of fellow ex-cons - all experts in their fields - including Wilson Cromartie, a fearsome Apache.
As Macklin plans his crime, Paradise police chief Jesse Stone has his hands full. He faces romantic entanglements in triplicate: his ex-wife, Jenn, is in the Paradise Jail for assault, he's begun a new relationship with a Stiles Island realtor named Marcy Campbell, and he's still sorting out his feelings for attorney Abby Taylor. When Macklin's attack on Stiles Island is set in motion, both Marcy and Abby are put in jeopardy. As the casualties mount, it's up to Jesse to keep both women from harm.