"Grand Cayman may be famous for its SCUBA diving and offshore banking, but with several daily non-stops from New York and Boston, it’s increasingly drawing families to its powdery, placid western Caribbean beaches. On the island’s Seven Mile Beach—one of the loveliest stretches of sand in the world—you'll find the 266-room Kimpton Seafire Resort & Spa, with a boutique atmosphere that manages to be both child-friendly (two pools, a kids' club) and hip (colorful, contemporary design and a lobby scene replete with pool table, library, and daily happy hour). The food is also strong: Hit beachside Coccoloba for fish tacos and ceviches; Ave, the resort's primary restaurant, for epic breakfast buffets (including house-made cronuts); and the sceney Avecita for progressive Spanish fare like white anchovy toast and prawn tartare, served up alongside craft cocktails at the chef’s counter. You can always snorkel and parasail right off the hotel’s beach, but you’re also just a short ride from Stingray City (where you can stand on a sandbar and touch giant rays as they swim by), world-class gardens (look for the endangered blue iguana), golf, and roadside jerk chicken. Hit Rum Point to toast the sunset—or maybe you'll prefer doing that from your own private balcony."