Willemstad, the capital of Curaçao, is unlike any other city in the Caribbean. With its pastel-colored buildings lining the waterfront and a layout shaped by Dutch colonial planning, the city blends European design with Caribbean culture. Its historic center, divided by Sint Anna Bay into Punda and Otrobanda, has been recognized as a UNESCO World Heritage Site.

Cancún sits on the northeastern tip of Mexico’s Yucatán Peninsula, where the Caribbean Sea meets a narrow stretch of sand shaped by ancient Maya trade routes and modern development. While widely known as a resort destination, Cancún’s roots trace back to a quiet fishing area near important pre-Hispanic sites, with nearby Isla Mujeres and the mainland serving as part of a broader coastal network connected to inland Maya cities.

Lyttelton is the largest settlement on Lyttelton Harbour, an inlet on the northwestern side of Banks Peninsula, and provides a frequent landing spot to those who are Christchurch bound.

Saint John is a culturally-rich seaport city on New Brunswick's Bay of Fundy. History and natural wonders combine to make this locale a hidden Canadian gem.

Tenby sits on the Pembrokeshire coast of southwest Wales, where medieval walls still encircle a compact town above the sea. Its history as a fortified port is visible in stone ramparts, narrow lanes, and the ruins of Tenby Castle, which overlook the harbor.