Head to Valparaiso’s Plaza Sotomayor to meet your guide in the afternoon. You’ll begin your excursion with an introduction to this historic port city from your guide, following along as you explore the town’s ‘Aduana’ building (part of an area owned by the Chilean military) along with the variety of French-influenced structures that surround this charming square.
Continue your trip by funicular, one of the most iconic transportation systems of this South American city, as you ascend to the Cerro Alegre and Cerro Concepción areas. In addition to gorgeous views of the ocean and greater Valparaiso, these two neighborhoods increasingly boast a thriving mix of boutique hotels, tasty eateries and eclectic retail outlets all housed in a colorful mix of charming buildings.
After leaving these hilltop districts behind, descend back down to Valparaiso’s Old Town, where you’ll have time to wander through its mix of narrow streets and ancient architecture. Finish the day by riding aboard 1950s-era trolley bus, famous as the second-oldest transportation service in South America, before ending at your original departure point.