After pickup in select districts of Santiago (Providencia, Vitacura, Las Condes, and Santiago Centro) by private vehicle, your day trip starts with the drive toward Chile's coast. Wind through Curacavi Valley on your way to Casablanca, where you'll stop at an organic winery for a tasting of olives and wine.
Then continue toward the Pacific to reach Valparaíso, a port city and the country's 2nd-largest metropolitan area whose historic quarter is a UNESCO World Heritage site. With your guide, explore its architecture, houses, and elevators, and visit La Sebastiana, a former home of Pablo Neruda's. Then see five of the city's most significant sites: Plaza Sotomayor, Paseo Yugoslavo, 7 Esquinas, Paseo 21 de Mayo, and the Valparaíso Lighthouse.
Finally, leave Valparaíso and head to Viña del Mar, where you can have lunch at a restaurant (own expense) before visiting the Flower Clock (Reloj de Flores), one of the main attractions. You'll also see an original Moai from Easter Island before starting the drive back to Santiago, stopping along the way at Las Palmas. Your tour ends with drop-off at your pickup location.