Three kilometers north of Cachagua and 80 kilometers from Viña, curving tree-lined streets nearly block the view of the ocean at Zapallar, originally part of Francisco Javier Ovalle’s Hacienda Catapilco. After inheriting the property in 1884 and making a tour of European beach resorts, his son Olegario began to give away lots to his friends on the condition that they build houses within two years, and Zapallar quickly became an elite community for monied Santiaguinos.

The 1906 earthquake destroyed many early buildings, but Zapallar’s inhabitants rebuilt with a vengeance, creating some of the coast’s largest and most elegant properties. Now a zona típica national monument, Zapallar is an eclectic mix of colonial-style casas, neo-Gothic mansions, and fashionably rustic villas, on large lots with extensive gardens. The Rambla, a broad footpath, follows the coastline.

Many founding families still own properties here. Among the notable mansions are those of Manuel Vicuña Subercaseaux (1912) and Carlos Aldunate Solar (1915), both designed by Josué Smith Solar; the extravagant castle of painter Álvaro Casanova; and María Luisa MacClure’s Bavarian-style Casa Hildesheim.

Directly on the highway, the 39-room Hotel Isla Seca (Camino Costero s/n, tel. 033/741224, fax 033/741228, www.hotelislaseca.cl, US$130–250 s or d) consists of two separate units a short distance apart; despite the roadside location, traffic is not heavy and the spacious rooms, which include balconies, face the ocean. Some have Jacuzzis. There’s also a handsome bar/restaurant.

On the beachfront César (Rambla s/n, tel. 033/741507) is an upscale seafood restaurant with outdoor as well as indoor seating. To the south, reached either by the curving Rambla or by road, Chiringuito (Caleta de Zapallar s/n, tel. 033/741024) has better views, more charm (with its crushed-shell terrace and asymmetrical tables), and arguably fresher fish straight off the boat.