Colonia del Sacramento is where time lingers. Founded in 1680 by the Portuguese and later contested by the Spanish, the town’s past is etched into its cobblestone streets and weathered facades. The Barrio Histórico, a UNESCO World Heritage Site, is compact enough to walk in an afternoon yet layered with centuries of stories. Visitors can explore remnants of the original city walls and climb the iconic lighthouse for sweeping views of the Río de la Plata.

Honolulu, the capital of Hawaiʻi and the largest city in the Pacific, blends the energy of a major urban center with the deep roots of Native Hawaiian culture. Set on the island of Oʻahu, it’s home to iconic beaches, royal history, and a rhythm all its own. This sunny capital city is the main portal to the larger Hawaiian archipelago, and the perfect base for exploring Oahu.

Though it's San Diego County's smallest city in both size and population, Del Mar is one of its most widely known due to prominence of its Del Mar Race Track & Fairgrounds. The City of Del Mar with about 2 square miles of land for its 5,211 residents, the city gives up almost one quarter to the fairgrounds. But its beaches stretch from Del Mar Shores Beach Park in the north edge of Torrey Pine State Reserve and the La Jolla Underwater Park in the south.

Sheffield, once the global heart of the steel industry, has evolved into a city where industrial heritage meets green landscapes and a growing creative scene. Known historically for innovations like stainless steel, Sheffield still celebrates its roots at sites like the Kelham Island Museum, where restored machinery and interactive exhibits tell the story of the city’s engineering legacy.

Carriacou, the largest of Grenada’s sister islands, offers a slower pace of life and an intimate window into traditional Caribbean culture. Known as the “Island of Reefs,” it is surrounded by vibrant coral systems that have long supported fishing and sailing traditions.