Santo Domingo’s most historic neighborhood is also its most romantic, lively, and cultural. Once the home of Spanish colonialists, who built the walled city as a model for the rest of the Americas, it’s an area brimming with museums, churches, shopping, theater, restaurants, and parks. Stay in a former colonial home turned boutique hotel, stroll the pedestrian Calle El Conde, dotted with shops, sidewalk cafés and street side art, and dine across lantern lit plazas. Along the way, visit the oldest sites in the Americas, including the first cathedral, the first paved street, the first monastery, the first hospital, the first university, and the first military fortress.