Santiago is one of those metropolitan joys where the more you look, the more you find. Funky cafes and dance clubs dot Bellavista, Forest Park art collections range from pre-Columbian to contemporary, and architecture runs the gamut from the 16th-century San Francisco Church to mirrored office towers. Shop with the locals at Mall Panora¡mico and give your palate meals to remember with hearty Chilean fare.

Chile's fourth largest city, Vina del Mar in Valparaiso, is also a popular summer beach resort. A Mediterranean climate prevails and an appealing array of sandy strips beckons, including Renaca, Miramar, Las Salinas and Casino. Renaca's calm waters and great waves make it a hit with families.

Only 70 miles northwest of capital Santiago, Valparaiso is Chile's main port and known for its bohemian, artistic vibe and lovely vistas. Its UNESCO-designated historic downtown offers charming colonial architecture, great seafood restaurants, markets and stores. Take 100-year-old funicular Ascensor Artilleria or climb Cerro Concepcion for stunning ocean and city views. Back at street level, visit writer Pablo Neruda's house.

Christ Church is located on the southern end of the island of Barbados, on the vibrant South Coast. Have fun travelling from beach to beach in a reggae boogie-bus and in the evening, charter a sunset cruise or head out to a seaside club and dance the night away. Sunbathe, snorkel or jet ski at a choice of beaches. If you prefer a quieter beach setting, it’s very easy to find one. The island has many long, isolated stretches of perfect white sand and crystal blue waters.

Antigua has hundreds of beaches, from the bustling Pigeon Point to the kitesurfing paradise of Jabberwock Beach. It's fun to mix it up—a day spent in a secluded cove, another spent people-watching at a tourist magnet. When you’re tired of sun and sand you can shoot ‘em up at Reservoir Range, where archery and air pistols are a fun way to work out any lingering pre-holiday stress. A tour of the Antigua Distillery is a spirited way to experience a true taste of the island.

U.S. citizens still need to jump through a few hoops to visit Cuba, but as visitors from around the world know, this island offers some amazing opportunities for cultural exchange. Havana is a mix of old-world architecture and of-the-moment culture. Head out of the capital city to the small town of Trinidad to see more Spanish colonial architecture. It’s a UNESCO World Heritage Site and a fantastic home base for a visit to the Valley of the Sugar Mills, a pocket of land that formerly served as the centre of Cuba’s sugar industry.

In the sweltering Georgia heat, no place is as cool as Athens. This hip college town is home to the University of Georgia, Pulitzer Prize winning authors and famous rock musicians. Explore the downtown area, where Victorian buildings are filled with an eclectic combination of independent coffee shops, restaurants and boutiques. Named "Live Music Central," Athens' busy music venues are known around the world. Check out The 40 Watt Club, where The B-52s and R.E.M got their start.

Dubbed the Queen City, Charlotte reigns over a 300-square-mile (482-square-kilometre) hodgepodge of neighbourhoods that spin out from the banks of the Catawba River. From brewery-heavy art districts to historical corridors dripping in charm, consider Charlotte a crowd pleaser.

As Baja California Sur’s capital, La Paz is mostly used as a jumping-off point for Cabo San Lucas’ beach resorts. However, its old-world charm and pleasant waterfront promenade featuring international art and restaurants overlooking the grey whale–inhabited water are reasons worth sticking around.