The Ultimate Long Weekend in St. Helena

  • Guides
  • on JULY 27, 2016
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St. Helena is the beating heart of the Napa Valley wine scene, so spend a long weekend here to experience the best in wine, dining, art, shopping, and small town life. We’ve created this 72-hour itinerary with three themes to show you the different sides of St. Helena. Read on to discover your perfect trip in St. Helena.

Day 1: Wine & Dine

One-Stop Shopping: Spend the rest of the morning exploring The Culinary Institute of America which is just down the road. Hop over there for wine and food. The student-run cafe and restaurant are open daily, and the corkscrew museum and gift shop are worth checking out.

Image Source: Trinchero, Yelp

Local Wine Tasting: Squeeze in more wine tasting at some of the local wineries, all of which are fantastic. We recommend Sinegal Estate for intimate, understated elegance, Anderson’s Conn Valley for powerful Cabernets, Trinchero Napa Valley for a lively and newly renovated tasting room, and Freemark Abbey for some great Napa Valley history and classic wines.

Insider tip: Most wineries close by 5 p.m., so head back into downtown St. Helena after hours for tasting rooms that stay open a bit later, like Orin Swift (open until 6 p.m.).

Dinner: Dine at Press, which not only serves some of the best steak in Napa Valley, but boasts the deepest Napa Valley wine cellar in the world. 1968 Cabernets? No problem. 1974 Chardonnays? Coming right up.

Insider tip: Order the Snake River Farms American Wagyu, cooked on an almond and cherry wood grill. Pairing with an aged Napa Valley Cabernet Sauvignon, creates a combination that’s tough to top.

Image Source: Arena Art Gallery, Yelp

Sleep: St. Helena’s charm doesn’t stop at nightfall. The town boasts some of the best overnight accommodations in Wine Country. Wydown Hotel keeps you in the middle of the action with a location right on Main Street, half a block from St. Helena’s best restaurants and art galleries.

The modern decor and attentive staff create a restful place to return to after a long day of adventure. If you’re really looking to relax, treat yourself to a weekend at Meadowood, one of Napa Valley’s most luxurious and comprehensive resorts. Tucked against the base of the Vaca Mountain Range and just a three-minute drive from downtown St. Helena, Meadwoood offers everything you’d expect of a Napa Valley resort: pools, spa, tennis courts, golf course, croquet course, and a three-Michelin-star restaurant.

Insider tip: Can’t afford Meadowood’s luxury pricing? Get a taste of the experience by lunching at The Grill, a relaxing restaurant on the golf course serving fresh, classic grill fare at less eye-popping prices than the Restaurant at Meadowood nearby.

Day 2: Art, Art, Art

Breakfast: Begin your art-focused day at Model Bakery on Main Street. Literally surrounded by art galleries, there isn’t a better place in town to fuel up for a day of artistic inspiration. Famous for their airy English muffins, the breakfast sandwiches and coffee are great choices too.

Insider tip: Try the savory tart, baked fresh daily with local vegetables on top like onion, mushroom, tomato, asparagus and artichoke.

Image Source: Arena Gallery, Yelp

Main Street Gallery Stroll: St Helena’s Main Street is packed with high end art galleries, showcasing everything from modern sculpture to oil paintings. Caldwell Snyder Gallery represents some of the best contemporary artists around, while the AErena Gallery is home to modern furniture, sculpture, and fashion collections.

Insider tip: Nimbus Arts is a locally owned art center and school with classes, seminars, camps, and more. Check out their website for events happening during your visit, like Paint & Sip on Saturday nights.

Shopping: Anyone who knows and loves fashion will argue that it’s possible to put art on feet, and Foot Candy certainly proves them right. The shoes displayed alluringly in this Main Street boutique are footwear at the peak of its artistic form, from strappy sandals to sleek knee-high boots.

Insider tip: Check out the back of the shop, where boutique designers sell their threads. Pick a trendy outfit to match that new pair of Jimmy Choos.

Lunch: Dining can be an art, and lunch at Harvest Table is like a classic oil painting with some bright colors thrown in to freshen it up. Chef Charlie Palmer opened his Wine Country kitchen in 2015 to rave reviews, and hasn’t stopped serving up satisfied diners since. The atmosphere is warm and welcoming, and the food is fresh and California-inspired, sourced from some of California’s most respected purveyors like Tolenas Farms Quail, Masami Cattle Ranch, and Sebastopol Berry Farms.

Insider tip: Order the crispy pig ear salad with cilantro and Yuzu vinaigrette for a light lunch.

Art and Wine: Combine two of St. Helena’s specialities with a visit to HALL St. Helena. Founded by former U.S. Ambassador to Austria, Kathryn Hall, the winery specializes in Napa Valley Cabernet Sauvignon and modern art displays. Grab a glass and stroll through the indoor gallery, or step outside to wander between towering modern sculptures by some of today’s most renowned artists, including John Baldessari, Jim Campbell, Nick Cave, and Jaume Plensa.

Insider tip: To truly geek out, sign up for the HALL Art & Architecture Tour, which guides visitors through a 45-minute tour of the property, wine in hand, available every Sunday at 11 a.m.

Paso Terra Seafood
Image Source: Terra Restauran, Yelp

Dinner: Who says art has to be on the wall? Terra creates it in the kitchen and serves it beautifully on your table. Named to the San Francisco Chronicle’s list of Top 100 Restaurants eight times, Terra doesn’t miss a beat when it comes to flavor, presentation, and service. Owners Hiro Sone and Lissa Doumani blend French and Japanese cuisines seamlessly with dishes like grilled scallops with Tosaka seaweed, and lobster tortellini with Shimeji mushrooms.

Insider tip: Save room for dessert – the apricot almond bisteeya with yogurt and wildflower honey is exquisite.

Day 3: The Local’s St. Helena

Image Source: Napa Valley Coffee Roasters, Yelp

Breakfast: Start the day at a local hangout, Napa Valley Coffee Roasters, located off the beaten path, one block west of Main Street. Order your morning beverage of choice and a muffin, and settle in to watch the wine industry elite do the same.

Insider tip: Grab a seat on the outdoor patio if you can: it’s perfectly positioned to watch the bustle of St. Helena waking up, from parents dropping children off at school to retired celebrities walking their dogs.

Image Source: Crocker & Starr, Yelp

Wine Tasting: Discover what the locals already know, that Charlie Crocker and Pam Starr make some mighty fine Cabernet Sauvignon at Crocker & Starr. The quaint winery is located just outside of town and offers private tastings by appointment.

Insider tip: If you have the time, reserve the Al Fresco Experience, a 90-minute tasting which includes cheese and charcuterie paired with Crocker & Starr estate wines.

Image Source: The Big Dipper, Yelp

Lunch: Combine wine tasting and lunch at Charles Krug, one of the valley’s original wineries. They fire up the pizza ovens from 11 a.m. to 4 p.m. on weekends, so you can order a couple pizzas and fill your glasses, then relax on the shady lawn.

Insider tip: After lunch, treat yourself to an ice cream cone at The Big Dipper. Located one block west of Main Street, this classic small town ice cream shop offers the good stuff—like Chocolate Orange Confetti—without the frills.

Image Source: The Cameo Cinema, Yelp

Dinner and a Show: Do as the locals do on weekend nights and enjoy a popcorn dinner at the Cameo Cinema on Main Street. This historic little theater was built in 1913 and received a facelift in 2015, including plush new seating and one of the best sound systems in U.S. It plays a mix of mainstream, independent, and documentary films, and hosts various events throughout the year, including the rapidly growing Napa Valley Film Festival each November.

Insider tip: If popcorn doesn’t quite do it for you, grab dinner at Cook Tavern before the show. Located just down the street, Cook Tavern has a solid American menu and beers on tap.

Drinks: End the day by walking over to Goose & Gander, a Wine Country public house (aka restaurant) and head straight for the basement bar. This bar was one of the epicenters of the craft cocktail movement that began in the U.S. a few years ago, and although legendary bartender Scott Beattie has departed, the cocktail program here is still strong. The low ceiling, aged wooden booths, and cozy stone fireplace transport you to a pub in England, but the cocktails brimming with freshly picked herbs, vegetables, and fruit bring you right back to California. Insider tip: Order the Cucumber Collins for a treat for both your eyes and your taste buds.

Whether you have one day, three days, or a lifetime, St. Helena is a gem of a town to explore. Grab your sunglasses, polish up your wine glass, and dive into wine country’s most picturesque treasure.


WineCountry Collective

WineCountry is made up of a dedicated and passionate team of wine, food, and travel aficionados. We diligently explore regions, both near and far, to curate the best ideas and resources. Whether you're musing over your next wine escapade, planning a romantic weekend away, embracing the Wine Country lifestyle at home, or are simply looking to be entertained for a moment, trust us to be your comprehensive guide.