Uncorking Memories: A Napa Valley Escape for Two Generations

Day one is all about signature Napa: wineries that define the region’s reputation for excellence and hospitality. Begin at Cakebread Cellars, known for its warm, approachable atmosphere and signature buttery chardonnay. Their casual, small-group tours offer an easy introduction to Napa Valley’s winemaking history, making it a great starting point for wine newcomers and enthusiasts alike.

In between tastings, stop at Oakville Grocery, a local favorite and the oldest continuously operating grocery store in California for a relaxed, casual lunch. Grab a sandwich or seasonal salad, and don’t miss their signature frosé.

In the afternoon, head to Far Niente, where the beautifully manicured estate, tucked into the hills of Oakville, feels like a storybook setting, perfect for photo ops. Don’t miss the cave tour, which offers a peek into their impressive barrel-aging process and a chance to explore one of the most scenic properties in the valley.

After your tastings, head back to your hotel to freshen up before dinner at Mustards. A beloved institution for over 30 years, Mustards blends elevated comfort food with a wine country sensibility. Think wood-fired meats, fresh local produce, and a wine list that celebrates the best of Napa.

Day two is all about the porch—slow sips, sweeping views, and cozy corners that make you want to linger. Start your morning at La Cheve, a charming, family-run Mexican bakery and café located in a historic building in downtown Napa. Known for its housemade conchas and breakfast burritos, it also serves excellent coffee, horchata cold brew, and a rotating menu of pan dulce. Fuel up here—today’s big breakfast will set you up for a day of indulgent tastings.

First stop: Stags’ Leap Winery, one of Napa’s most storied estates. (Be sure you are visiting Stags’ with the apostrophe after the s.) Choose their historic estate tour to hear tales of the property's speakeasy during Prohibition and the resourceful wife of the original owner, who disguised wine production as sacramental to keep it going. Or, lean into your porch-loving, wine-country-dreaming energy with their Porch Tasting, where you’ll sip wines while overlooking the rugged Palisades and the vineyard-draped valley.

Next, head to Caymus Vineyards, where time slows down on their idyllic patios. It’s the kind of place where you could easily lose a few hours nestled among blooming gardenias, redwood trees, and shaded courtyards. Founded in 1972 by Charlie and Lorna Wagner, Caymus remains proudly family-owned, rooted in land the Wagners have farmed for generations. Their bold, fruit-forward cabernet helped define Napa’s signature style, and that legacy is felt in every sip and in the relaxed, welcoming atmosphere that makes this winery feel more like a home than a tasting room.

End your day with dinner at Charter Oak in St. Helena, an inviting, ingredient-driven restaurant housed in a former winery. The menu is centered around open-fire cooking and seasonal produce sourced from their own farm, served family-style. Don’t miss their signature hearth-baked sourdough, crudités with fermented soy dip, and grilled meats; this spot embodies Napa’s relaxed yet refined culinary spirit.

Day three is all about exploring the contemporary side of Napa, where bold design, modern architecture, and innovative winemaking come together. Start your morning with a breakfast sandwich from Contimo Provisions, a local favorite known for its flaky, housemade buttermilk biscuits layered with farm-fresh eggs, cheese, and seasonal ingredients. Or, head to Oxbow Public Market and stop at The Model Bakery for one of their famous English muffin breakfast sandwiches (Oprah-approved)—they're griddled to golden perfection, with a pillowy texture that puts store-bought muffins to shame.

Your first tasting will be at Ashes & Diamonds, a standout for its mid-century modern aesthetic and minimalist tasting spaces that channel vintage California cool. The wines here focus on restrained, food-friendly styles that nod to Napa’s past while pushing forward with precision and balance.

Then head to Artesa, an architectural marvel built into a hillside with panoramic views of Carneros. Known for its sleek, modern design and large-scale sculptures, Artesa was also a filming location for the Tina Fey comedy Wine Country. It's as much a visual experience as it is a tasting one.

End your day with dinner at Farmstead at Long Meadow Ranch, a rustic-chic restaurant. The menu highlights organic produce, grass-fed beef, and wines from their own vineyard, all served in a warm, barn-inspired space that’s both relaxed and refined.

Day four is your exclusive (or let’s just say it—bougie) finale, the perfect way to end your trip in unforgettable style. This day is all about elevated experiences that feel personal, indulgent, and a little harder to come by. To embrace the elevated life on your last day, sleep in and enjoy room service.

Start with a visit to Scribe Winery, my personal favorite. Located just over the hill in Sonoma, Scribe offers a glimpse into a different side of wine country: relaxed, effortlessly cool, and deeply connected to the land. Set on a historic property with sweeping vineyard views and a lovingly restored 19th-century hacienda, Scribe feels more like a dreamy retreat than a traditional winery. Their wines (vibrant, nuanced expressions of pinot noir, chardonnay, and skin-fermented Sylvaner, among others) are consistently outstanding. But what truly sets Scribe apart is the experience: tastings are exclusively for members, making it feel intimate and intentional. I highly recommend becoming a member to enjoy their signature Hacienda tasting, which includes a curated flight paired with chef-prepared, seasonal snacks. And once you're part of the family, your return visit could include their beloved picnic tasting, a laid-back afternoon on the lawn with a chilled bottle and a blanket, soaking in the beauty of Sonoma. It's the kind of place that lingers with you long after the last sip.

Cap off your trip with a once-in-a-lifetime dinner at The French Laundry in Yountville. Chef Thomas Keller’s legendary restaurant is a three-Michelin-star experience known for its meticulous technique, flawless service, and tasting menus that highlight the best of Napa’s seasonal ingredients with French finesse. From the iconic blue door to the famously well-orchestrated nine-course meal, every detail is designed to surprise, delight, and leave a lasting impression. If there’s ever a night to dress up, toast big, and savor every bite, this is it.