The Napa Valley unfolds like a vintner's dream: a 30-mile stretch of fertile land cradled between two mountain ranges, where world-class wines, innovative cuisine, and luxurious resorts create a sumptuous destination for those seeking the finer things in life. While its reputation was built on wine—some of the world's most celebrated Cabernet Sauvignons are produced here—today's valley offers much more than exceptional tastings.
This itinerary begins in the south with the city of Napa: Once a sleepy river town, it’s now a vibrant cultural hub with a thriving arts scene and innovative dining options. As you travel north along Highway 29 and the parallel Silverado Trail, each community reveals its own distinct character: sophisticated Yountville with its constellation of Michelin stars, historic St. Helena’s refined charm, and Calistoga's laid-back vibe and healing hot springs. Here's how to experience the best of the valley in just 48 hours.
Day One: Downtown Napa
Walk Around Napa
Begin your Napa Valley adventure at Oxbow Public Market, a 40,000-square-foot culinary wonderland that exemplifies the region's gastronomic spirit. Start with coffee and pastries from Model Bakery (their English muffins earned Oprah's seal of approval) before exploring the market's many artisanal vendors. The outdoor deck overlooking the Napa River provides a perfect spot to enjoy barbecued bivalves from Hog Island Oyster Co. or wood-fired pizza from Live Fire Pizza while planning your day.
Take time to explore downtown Napa's walkable core, where historic Victorian buildings house contemporary boutiques and tasting rooms. Pop into Makers Market for locally crafted goods or browse the curated collection at Copperfield's Books. For art enthusiasts, the Rail Arts District offers an impressive collection of outdoor murals.
Unique Wine Tasting: Napa Valley Wine Train
Board the Napa Valley Wine Train for a unique perspective on the valley. This restored vintage rail line offers a variety of multi-hour journeys through the heart of wine country. From the comfort of your plush seat in a century-old Pullman car, watch the landscape of brand-name vineyards roll past while enjoying a gourmet lunch and carefully selected local wines. The train's route offers views of renowned wineries like Grgich Hills Estate and Charles Krug, providing context for the valley's rich viticultural history.
Seasonal Italian Dinner at Oenotri
For dinner, secure a table at Oenotri, where southern Italian cuisine meets the region’s substantial local bounty. The restaurant's housemade salumi and wood-fired pizzas are the stars, but don't miss the daily-changing pasta selections that showcase seasonal ingredients from their four-acre culinary garden. The extensive wine list features both Italian varietals and local favorites.
Overnight Stay at Archer Hotel
Retire for the night one block away at the Archer Hotel, downtown Napa's sophisticated anchor. This urban-chic property offers stunning rooftop views from its Sky & Vine Rooftop Bar. Take advantage of the evening to enjoy a nightcap by the fire pits while watching the stars materialize above. (Alternative lodging options include the stylish Andaz Napa and the intimate Inn on Randolph.)
Day Two: Yountville, St. Helena, and Calistoga
Breakfast and Shopping
As your second day begins, head north along Highway 29, the valley's main artery, making your first stop at Honor Market in tony Yountville. This reimagined gas station epitomizes the valley’s blend of practical and luxurious, offering artisanal coffee, gourmet provisions, and a carefully curated wine selection alongside—yes—fuel pumps.
Continue to irresistible St. Helena, where Main Street offers one of Northern California's most charming shopping experiences. Stop at Olivier Napa Valley to sample their oils and vinegars, browse cookware at Steve's Hardware & Housewares (a local institution since 1955), and venture off the main drag to explore the artisanal food products at Napa Valley Olive Oil Manufacturing Company, housed in a historic barn since 1931.
Wood-Fired Lunch at The Charter Oak
Lunch at The Charter Oak represents wine country dining at its finest. Chef Christopher Kostow (formerly of the venerated Restaurant at Meadowood) creates sophisticated yet approachable dishes cooked over open fire. The stuffed Petaluma chicken and “Raw Vegetables From Our Farm” have achieved cult status, while the historic building's exposed brick walls and soaring ceilings provide an atmospheric backdrop. On a warm day, the lush outdoor patio is hard to beat.
Relax in Calistoga Hot Springs
Continue north and check into Indian Springs Calistoga, where California's oldest continuously operating pool is fed by natural geothermal geysers. The property's 17 acres feature gardens, meditation areas, and an Olympic-sized mineral pool built in 1913. Book a mud bath treatment—a Calistoga tradition—or simply lounge by the smaller adults-only pool surrounded by palm trees and mountain views.
Taste Wine With a View at Sterling
It’s time for another splash of wine, so take the aerial tram to Sterling Vineyards, where the hilltop winery offers some of the valley's most spectacular views. The Greek-inspired white stucco architecture houses excellent wines, but it's the gondola ride and panoramic vistas that make this experience unforgettable. Time your visit for late afternoon to catch the valley in its golden hour.
Michelin-Starred Dining in Napa: Auro at the Four Seasons
Conclude your weekend at Auro, where Chef Rogelio Garcia's Michelin-starred cuisine showcases the valley's bounty through a contemporary California lens. The restaurant's intimate dining room within the Four Seasons Resort provides a fitting finale to a weekend of indulgence. Garcia's constantly shifting tasting menu might include dishes like Japanese bluefin tuna or dry-aged Australian Wagyu, each course thoughtfully paired with wines that tell the story of the valley.
From sophisticated urban pleasures to rural charm, historic legacy to contemporary luxury, the Napa Valley offers an enriching escape that explains why this relatively small valley has achieved such outsized renown. While two days only scratches the surface, it's enough time to understand why visitors find themselves returning again and again to this remarkable destination.