Refer to Vancouver Island as Victoria Island and risk a chorus of eye-rolls from the otherwise-friendly locals. Yes, Victoria is the main city on the island, but there are many distinct flavours to its logging and fishing settlements. Food and wine enthusiasts flock to the Comox Valley farm region, while the more outdoorsy types get their fix along the remote, forested beaches of North Vancouver Island. Visit the UNESCO Biosphere Reserve at Clayoquot Sound and you’ll return full of cocktail-party factoids.

Known as the home of “the happiest place on Earth,” there’s more to Anaheim than thrilling theme parks. Bring your appetite to the Anaheim Packing District and Centre Street Promenade for some eclectic eateries and award-winning craft breweries. Explore the latest exhibits at the Muzeo Museum and Cultural Centre. Enjoy live music at the all-new House of Blues, now at the Anaheim GardenWalk.

Stretching 126 miles south towards Cuba, the stunning Keys are a perfect escape. Highlights along the way include Key Largo, Islamorada, Marathon, Big Pine Key and the irrepressible Key West. Come face to face with an amazing array of fish while snorkelling, diving or fishing in the warm turquoise waters. Creeks, coral and costumed shows are other lures along the way. Highway 1 is a spectacular ribbon tying together the islands and atolls of this paradise between the Gulf of Mexico and the Atlantic.

San Pedro is "La Isla Bonita" that Madonna made famous. Now it's a tourist mecca, but still boasts great beaches and plenty of dive shops so you can enjoy the sun, sand, and sea. Plan a side trip to Caye Caulker while you're here; it is less developed and more laid back, and has its own splendid swimming areas.

The landscape is dramatic—even a bit moody, with the Cuillin Range in the background—but outdoorsy kids will have a blast on the Isle of Skye. Plenty of water sports are available, and you’ll also find great hiking and even pony rides. Portree, the largest town, makes a great base for exploring this striking island.