Tagaytay secures its place on most Philippines itineraries with its location above Taal Volcano's active crater. Views of the crater lake and a refreshingly cool climate make the town an enticing destination—not to mention the famously unfinished People's Park in the Sky.

Metropolitan Manila encompasses six cities and 12 towns. Located on Manila Bay in the South China Sea, and bisected by the Pasig River, the capital of the Philippines is historic and modern, rich and poor. A popular sight is the walled area called Intramuros. The capital during Spanish colonization, Intramuros has retained old dungeons and gunpowder rooms but added art galleries and theaters. The city is filled with museums, shops, parks and churches, plus enough nightlife to last until dawn.

Surpassed only by Manila in size, the Philippines’ second city combines colonial architecture and mountainous surrounds with a burgeoning cultural and culinary scene. As the gateway to both Bohol and Cebu Island, Cebu City impresses with chic rooftop bars and intriguing museums.

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.