Grand Cayman

Grand Cayman's best-known attraction isn't a beach or a building but a sandbar in open water. Stingray City began, according to the commonly told local history, when fishermen anchored in the North Sound to clean their catch, and the discarded scraps drew wild southern stingrays that gradually grew comfortable around boats and people. Decades later, dozens of rays gather reliably at the same shallow sandbar, and boat tours bring visitors to stand waist-deep and interact with them directly.

Seven Mile Beach, despite the name, runs closer to six miles along the island's western shore, but the shortfall hasn't dented its reputation — consistently fine white sand and calm, protected water along nearly its full length, backed by the island's densest concentration of resorts.

The Cayman Islands' lack of direct income or corporate tax has shaped the islands well beyond finance — it supports a large offshore banking sector that keeps the local economy unusually wealthy for the region, which shows up directly in higher hotel, dining, and activity prices than most Caribbean destinations.

That same wealth has funded genuinely well-regarded dive infrastructure. Grand Cayman's underwater wall, where the reef drops off dramatically into deep water close to shore, draws a dedicated diving crowd, and the deliberately sunk USS Kittiwake, a former submarine rescue ship, has become one of the region's most-dived artificial reefs since going down in 2011.

George Town, the capital, functions as both the cruise port and financial district, giving it an unusual mix for a Caribbean capital — cruise-ship souvenir shops sitting a few blocks from international banking offices, a direct reflection of the island's two main industries operating side by side.