Lucas Wackford

As a kid, fall always meant piling into my aunt’s Volvo and driving up to Apple Hill. The day was filled with farm-hopping, cider tastings, spiral-cut apples, and fresh apple donuts still warm from the fryer. There’s a timeless magic here: crisp mountain air, rolling orchards, and that cozy small-town festival spirit. For me, Apple Hill isn’t just about apples—it’s about tradition, nostalgia, and the simple joy of slowing down with loved ones.

Carneros is where Napa slows down and breathes—rolling hills, coastal breezes, and sparkling wine before golden hour. For small groups, it’s ideal: private cottages, fire pits for late-night conversations, and world-class wineries minutes away. I’ve built this itinerary so you can park the car, exhale, and let each day unfold with intention—elevated but easy, celebratory but never rushed. Expect thoughtful food, terroir-driven tastings, and plenty of time together.

Aspen is more than a ski town—it’s an intersection of mountain adrenaline, cultural sophistication, and wellness retreat energy. Powder mornings roll into gallery strolls, après on sunlit terraces, and nights under starry skies. What keeps me coming back is how Aspen balances rugged wilderness with refined living—every trail, spa, and restaurant has its own character. Whether you’re here for the slopes, the festivals, or simply the crisp mountain air, Aspen has a rhythm that shifts with each season.

Lake Como is where old-world villas, glassy water, and modern design quietly meet. Mornings begin with mist on the mountains, afternoons unfold on a wooden boat between storybook towns, nights are for candlelit dinners and soft jazz on a terrace. I love how each village has its own rhythm—Bellagio’s bustle, Varenna’s romance, Tremezzina’s dolce-far-niente. This guide leans luxe but stays local: unhurried, detail-driven, and built around savoring the lake rather than racing around it.

Lake Tahoe is where I go when I want luxury and nature to meet seamlessly. It’s a year-round playground: powdery ski slopes in winter, glassy blue waters in summer, and crisp alpine air every season in between. Here, mornings start with espresso overlooking the lake and afternoons end with a fireside après-ski or champagne at the water’s edge. Tahoe’s magic is its duality—wild yet refined, adventurous yet indulgent.

There’s nothing quite like standing at the edge of Big Sur’s cliffs, where the Pacific feels endless and life slows into pure presence. This coastline is both grounding and elevated, where five-star dining meets barefoot walks on the beach. Carmel adds the charm: cobblestone streets, tucked-away galleries, and candlelit inns. Together, Big Sur and Carmel create a seamless blend of rugged nature and refined indulgence.

Healdsburg is where Wine Country slows down and levels up. I come here to design moments—sunset tastings under redwoods, chef counter dinners, and late-night rooftop cocktails—with everything walkable from the Plaza. Between SingleThread’s rarefied hospitality and The Madrona’s painterly charm, it’s a masterclass in indulgence. Come for the Pinot and Chardonnay—stay for the ritual of beautiful days well-planned.

San Francisco has always held a special place in my heart. It’s a city that transforms at night—alive with energy, art, and possibility. From social activations at W San Francisco, dinner with friends at Beretta on Valencia, to sweating it out on the dance floor at Audio, the city offers unforgettable moments at every turn. San Francisco truly embodies the feeling of a city that never sleeps, with a nightlife culture that is as diverse as it is inspiring.