Napa Valley's Silverado Trail

The bustling city of Napa, on the banks of the Napa River, features chef-driven restaurants, upscale lodgings, manicured parks and river walks, and multiple tasting rooms. The downtown dining scene is a delight, ranging from the ultra-authentic pastas and pies at Oenotri to Kenzo, a Japanese restaurant that boasts a Michelin star and a Wine Spectator Award of Excellence. After dinner, take in a show down the street at the outpost of New York City’s famed Blue Note, inside one of the region’s social and cultural hubs, the Napa Valley Opera House. For overnight stays, R&R abounds at options such as the big-city-chic Andaz Napa hotel and the impossibly romantic 1889 Churchill Manor B&B mansion.

This riverside food hall, located in Napa, is home to a number of local restaurants and producers, all gathered under one roof.

Bring a pour-over coffee from downtown Napa’s Ritual Coffee Roasters to Trancas Crossing Park near the base of the 167-year-old trail, and marvel at the kayakers launching into the current—a nice way to ease into the morning and simply observe.

This 33-acre park on the north side of Napa is ideal for kayakers, dog walkers, and anybody interested in experiencing the flora and fauna of the Napa River wetlands. Restoration of natural settings is a key focus of this park, which features a variety of trails and interpretive signs. Hall of Fame golfer Johnny Miller, a Napa resident, donated the property to the Land Trust of Napa County, enabling locals and visitors to explore before or after a wine-tasting excursion.

Who knew the placement of an apostrophe could prove so pivotal? In the Stags Leap district (no apostrophe) of the Napa Valley you’ll find a collection of wineries that all seem to specialize in Cabernet Sauvignon. These include Stag’s Leap Wine Cellars (apostrophe before the “s”), an esteemed institution that won big at the 1976 Judgment of Paris and helped put California on the world viticulture map. And don’t miss Stags’ Leap Winery (apostrophe after the “s”), a lovely and historic estate that dates back to 1893.

Raymond Twomey Duncan and Justin Meyer formed Silver Oak in 1972 with a firm commitment to one varietal, Cabernet Sauvignon, aged exclusively in American oak. This single-mindedness has paid dividends over the decades, establishing Silver Oak as one of the most consistent and food-friendly wineries in the Napa Valley. Visit the Oakville property, located just off the Silverado Trail, or the group’s Alexander Valley tasting room in Healdsburg.

Snag a terrace table at Auberge du Soleil, overlooking the valley. Its Michelin-starred three-course prix fixe menu changes regularly, but the overall gist is seasonal Cal-Mediterranean cuisine packed with local ingredients.

This 54-acre property, located on Howell Mountain to the east of the Silverado Trail, is a reminder that there are some terrific wines being made in the hills above the valley floor. If you like to mix politics with your pours, note that Cade Estate Winery lists California Governor Gavin Newsom as a co-founder. (Newsom is also a partner in nearby PlumpJack Winery and Odette Estate Winery.) Tastings here aren’t cheap—expect to drop $80 to $125 per person for a tour of the property—but you’ll be rewarded with epic views and some award-winning juice.

Drop your bags off at the unabashedly trendy though low-key Calistoga Motor Lodge. (Bonus: Hot spring water is pumped into the pools!)

Located at the northern tip of Napa Valley at the base of Mount Saint Helena, Calistoga is the less traveled, laid-back sister to the bustling downtown Napa. Calistoga’s local wine scene has attention-grabbing appeal—in part thanks to Castello di Amorosa, the medieval-style, multi-turreted castle on a hill built by Italian-style winemaker Dario Sattui. For a less traditional approach to grape juice, stop by the hipster-friendly Tank Garage Winery. It’s open seven days a week and specializes in blends with names like Yacht Rock, Backstage Pass, and Eddie. Wine is not the only elixir that people love here, certainly. Calistoga is the valley’s spa and hot springs capital, and visitors have flocked here seeking rejuvenation in mineral-rich volcanic waters since the 1800s. Spas and resorts range from casual to upscale, and most offer hot soaks, saunas, and massages. Calistoga is also a key spot to enjoy another Napa Valley signature experience: a hot-air balloon ride. Floating above the morning mist, looking out across the still valley as the sun peeks over the surrounding hills—can you imagine anywhere you’d rather be? While you’re in the part of wine country, if you find yourself passing through Fairfield, be sure to stop by the California Welcome Center there. The local staff will give you free maps, brochures, and inside tips on the area.