Harwich

Nestled into a particularly picturesque nook of Pleasant Bay, this unapologetically grand resort is top-notch through and through—everything from the manicured lawns to private cabanas to the four stellar on-site restaurants has been meticulously thought out. There’s a world-class golf course, tennis, and an adults-only pool, but the real action is, as to be expected, at the beach, where you and the kiddos can take sailing lessons among other watersports and activities. Accommodations-wise, choose between sprawling rooms in the main house, rustic cottage-style suites, or a sprawling private villa.