The elegant La Playa Carmel lives up to its nickname as the “Grande Dame of Carmel.” Originally built in 1905 for a Ghirardelli heiress, the hotel served as a go-to retreat for Apple founder Steve Jobs. The cliffside property recently underwent a $3.5 million makeover with renovated guest rooms, a new bar and lounge, and more (rooms start at $299). Carmel lies within Monterey County, which was recently named one of the country’s Top 10 Wine Travel Destinations by Wine Enthusiast. Oenophiles can take advantage of the scene with the new Grapevine Express, a bus that stops at 11 tasting rooms. This month’s events include the Taste of Carmel (October 3) and the Carmel Art & Film Festival (October 9–13).