Stretching along the southern side of Italy's Sorrentine Peninsula, the Amalfi coast dazzles with its mysterious grottos, craggy cliffs and shimmering bays. Grab a seat on the sea side of a regional bus to soak up views on the fabled route from artsy Positano to Amalfi. Ravello offers some respite from the crowds, plus the stunning Villa Cimbrone, which overlooks the Bay of Salerno. The historic section of Sorrento has winding streets filled with craftspeople. Capri is only a hydrofoil or ferry ride away.

Georgia’s capital, Tbilisi, is straight from the pages of a Gothic fairytale. A deep valley forms the backdrop to brightly colored turrets, cobblestoned streets, and a burgeoning art scene, while warm Georgian hospitality permeates the mix of contemporary and traditional restaurants serving up local favorites.

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 flavors 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.

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 center of Cuba’s sugar industry.

Is there anything better than stretching out like a cat in a warm patch of Jamaican sun? Only if you sprinkle your island vacation with a dash of adventure. Known fondly as “the land of wood and water,” Jamaica’s forests feature prime hiking and bird watching. History buffs can the heritage sites of Trelawny, while reggae and dancehall fans will love the authentic music clubs of Kingston. Montego Bay is perfect for snorkeling and shopping, while the spas of Ocho Rios can make any stresses melt away.

Sedona is a true oasis, a vacationer’s paradise in the middle of the Arizona desert. Here, you’ll find resorts and spas, canyons and red rock formations. Bell Rock and Oak Creek Canyon are great hiking spots, and the dramatic architecture of the Chapel of the Holy Cross is a religious experience itself. When the sun dips down below the horizon it introduces the best show in Sedona: the night sky.