Surrounded by water on three sides, Agios Nikolaos combines the sleepy feel of a seaside resort with all the amenities of a cosmopolitan port. Villas and tavernas spill over the town’s three hills to meet a harbor dotted with both mega-yachts and fishing boats.

Tiny Skiathos is packed with pine forests, archaeological ruins, and—most importantly—beaches. Shed your inhibitions at the nudist Banana Beach or have a more modest sun session at Koukounaries, which is peppered with lively cafes. Sail around on a chartered catamaran, hike to the dramatic medieval ruins of Kastro and tap into your spiritual side at one of Skiathos many monasteries.

The Singapore cityscape looks like it was ripped from the pages of a science fiction comic book. If you’re hungry for a true Singapore experience, sample the myriad street foods or take a cultural cooking class. The Botanic Gardens and the Gardens By the Bay offer a slice of horticultural heaven, and the observation deck of the Sands SkyPark makes you feel like you’re high above the clouds. The banks and walkways along the Singapore River bustle with local activity.