Villa de Leyva, Colombia

Whitewashed colonial squares, emerald highlands and bohemian mountain town charm in Colombia's heart.

Walk into Plaza Mayor at sunset and you'll get it immediately—this is the largest colonial square in South America, all 14,000 square meters of it, framed by white-washed buildings that look like they haven't changed since the 1500s. The kind of place where your friend group can spread out on the cobblestones with beers from a corner tienda and watch the light shift from gold to purple over terracotta roofs. This mountain town sits at 2,100 meters in the Boyacá highlands, which means cool nights perfect for group dinners around fireplaces, and days exploring pre-Columbian ruins, vineyards, and fossil beds without the sweaty chaos of Cartagena. The best things to do in Villa de Leyva blend historical sites with genuinely weird roadside attractions (there's a museum dedicated entirely to one enormous crocodile fossil), making it ideal for groups who want culture but also don't mind being a little silly. It's three hours from Bogotá but feels like another century—your squad trip here is…