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Winding Through Wine Country

Sample the flavors of the Napa Valley, Sonoma County, and the Anderson Valley on this scenic drive past rolling hills and endless vineyards

End:Stanford Inn By The Sea
2 - 5Days,11Stops,151Miles
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Stop 1


1290 Napa Town Center, Napa

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.

Plan your visit

Stop 2

Oxbow Public Market

610 1st St, Napa

This lively food hall is a perfect spot to taste fresh oysters at Hog Island, sample artisanal charcuterie from Fatted Calf, or indulge in truffles and caramels from Anette’s Chocolates. Pick up an organic wood-fired pie from the market’s Ca’ Momi, which has been certified by both the VPN (Vera Pizza Napoletana) and APN (Associazione Pizzaiuoli Napoletani). You’ll be sure to find something to savor in this 40,000 square foot facility, whether it’s a refined cappuccino at Ritual Coffee Roasters, a hearty IPA at Fieldwork Brewing Co., or a great read at Napa Bookmine.

Plan your visit

Stop 3


1020 Foothill Blvd, Calistoga

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?


Plan your visit


Tamber Bey Vineyards

1251 Tubbs Ln, Calistoga

Tamber Bey Vineyards is known for its Pinot Noirs and Cabernets, its herd of horses and, surprisingly, its cookies. Pair your tasting with a selection of the savory shortbread treats to bring out the best in the vintages.

Stop 5


401 Grove St, Healdsburg

The flawless-at-every-turn town of Healdsburg, at the north end of Sonoma County, was recently listed as the No. 2 “Best Small Town to Visit” in the U.S. by Smithsonian magazine. Indeed, Healdsburg is a pretty small town—with a population of a little over 11,000—but many of the names here have become pretty big. Take, for example, the lavish luxury lodgings like the Relais & Chateaux Hotel Les Mars; SingleThread, a farm/restaurant/inn trifecta that earned three Michelin stars; and Valette restaurant from local chef Dustin Valette. It’s easy to spend an entire day just wandering the environs of Healdsburg Plaza, lined with dozens of tasting rooms, each with their own vibe. Check out the big-city chic Cartograph with wines on tap, the stylish funky Banshee with its record player spinning vinyl, or sample some of Sonoma County’s acclaimed craft beer at Bear Republic Brewing Co.

Stop 7


13500 Airport Rd 95415, Boonville

This tiny town is hard to miss and impossible to resist for anybody driving to the coast along Highway 128. There are plenty of places to grab a bite here and you can sample the Pinot Noirs and other varietals at Foursight Wines, Bee Hunter Wine, or Seabass Family Wines. Pennyroyal Farm is another key attraction, and deservedly so. This 66-acre goat and sheep farm specializes in artisanal cheesemaking, and visitors can tour the creamery, meet the animals, explore the solar-powered barn, and sample the handcrafted wine. While this part of Mendocino County is definitely wine country, ale advocates will want to pay a visit to the Anderson Valley Brewing Co., a craft brewery known for its award-winning Boont Amber Ale and a Disc Golf course that is popular with locals.


Little River Inn

7751 CA-1, Little River

Five generations of innkeepers have been managing this inn. From lush gardens to a protected cove, you feel downright spoiled to be dining on local seafood and sipping on the North Coast’s award-winning wines.


Ole's Whale Watch Bar

7751 CA-1, Little River

Whale Watch Bar located at The Little River Inn is one of the North Coast’s favorite watering holes. Pull up a stool, order a pint, and keep an eye on the ocean for spouts.

Stop 10



Mendocino is a charming North Coast hamlet, perched on a wave-carved headland, sandwiched between thick forests and a restless sea. Its dramatic location is a natural magnet for artists, and you can often see them capturing the scene on their canvases. The town is meant for walking, so stroll the streets with shops selling local artwork, then pop in for a coffee and chat with the locals. Take a walk along the bluffs, especially at sunset on fog-free evenings. Victorian-era homes, converted into B&Bs in every level of poshness, look like gingerbread houses come to life. Mendocino also knows how to throw a good party, especially when it comes to food, and annual festivals celebrate mushrooms, wine, and crab, as well as the region’s largest inhabitants, whales.


Stanford Inn By The Sea

44850 Comptche Ukiah Road, POB 487, Mendocino

At The Stanford Inn by the Sea, pets are welcome, views are epic, and every stay includes mountain bike rentals and a daily chef’s breakfast using ingredients from the organic garden. Light your wood-burning fireplace and settle in for a good night’s rest.


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Road Trip Snapshot

Learn more about the amazing locations featured in this road trip. Ready to plan your trip? Print the itinerary or map your adventure to get started.

Stop 1Napa
1290 Napa Town Center, Napa
Stop 2Oxbow Public Market
610 1st St, Napa
Stop 3Calistoga
1020 Foothill Blvd, Calistoga
Stop 5Healdsburg
401 Grove St, Healdsburg
SPOTLIGHTOle's Whale Watch Bar
7751 CA-1, Little River
    Stop 10Mendocino

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