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Plan to spend at least two days in Valparaíso, where you can ride a few funiculars and explore the cobbled streets. While you're there, a good day trip is an excursion to Pablo Neruda's waterfront home nearby in Isla Negra. You'll want to take a day or so to stroll around the bustling beach town of Viña del Mar. After that you can drive north along the coastal highway, stopping for lunch in either Concón or Maitencillo. From there you can return to Viña del Mar or continue on to spend a night in Zapallar.