St. Helena

Winemaker Chris Phelps has a pretty good résumé, having spent time at Pétrus in Bordeaux, as well as Dominus and Inglenook in Napa Valley. The St. Helena native now manages his own project, Ad Vivum, a single Cabernet bottling sourced from the Sleeping Lady Vineyard in Yountville. Phelps is hands-on, so expect a wide-ranging conversation as he's one of the valley's more erudite winemakers. Phelps' son Josh may swing through as well; his value-priced Grounded Wine Co. is one of the valley's burgeoning projects.

1400 Oak Avenue

The Clif Family tasting room is a popular spot, thanks in part to the food truck parked behind it that offers delicious bruschetta along with salads, polenta tots and organic whole roasted chickens. The main tasting room offers the full range of the winery's broad portfolio, while the next door Enoteca provides private (by appointment) wine and food pairing experiences.

709 Main Street

The tasting room here, housed in the property's original 1886 stone winery, is decidedly low-key. The tasting room staff includes hosts with 20-plus years of experience, and winemaker Adam Casto is likely to stop by during your tasting. Ehlers also partners with next-door Alila on a pairing menu.

3222 Ehlers Lane

This 1878-dated structure (formerly home to St. Clement winery and part of Spring Mountain Vineyard before that) was purchased by the Huneeus family in 2016 and renovated in 2020. Offering a broader approach to wine tasting, you can find both local and international artisanal wares, jewelry, sculpture, leather goods, clothing and more, rotating on display throughout the year. There's a speakeasy in the basement where vinyl records can be played during tastings of library vintages, and there's always an eclectic mix of small bites served. And while the 2,500-square-foot space has several swanky rooms inside, the haus sits perched atop a sprawling terrace of vines that looks east over the valley.

2867 St. Helena Highway N.

Wines from the Lewelling clan, one of St. Helena's longtime families, are now made by sixth-generation Haley Wight. The tasting room pours the family's small-production Cabernet Sauvignons, along with Wight's own Hayfork brand, which features more offbeat bottlings of Marsanne and Charbono. In a simply adorned room with a single table in the middle and a wooden plank over a couple of barrels forming a counter, you'll be hosted by either Wight or her brother.

1282 Vidovich Avenue

Winemaker Diana Snowden lives in Burgundy, where along with her husband, Jeremy Seysses, she makes the wines for Domaine Dujac. She comes back to her native St. Helena a few times a year to oversee her family's vineyards and winemaking, so you might catch her in the tasting room. If not, someone else from the Snowden clan will be on hand. Visits are intimate in scale, as the family hosts only a single small group at a time in their bare bones tasting room. You'll get to talk farming, winemaking and more with the folks who do the work themselves.

1432 Main Street

This family-owned property has been run by the Novak family since 1972, though its history dates to 1882. The quintessential St. Helena estate, Spottswoode sits in the heart of the town's lush and verdant west side. There are different experiences offered, including a vineyard walk or a tasting of library vintages. Visits are by appointment only, with preference given to existing mailing list customers, so reserve well in advance. Note: No children or pets permitted.

1902 Madrona Avenue

Previously the owner of 750 Wines, a retail operation in St. Helena, Monica Stevens has been around the Napa wine scene for nearly two decades. Her latest venture is this collective tasting room. Stevens pours wines from five-dozen boutique-size labels (Hobel, Hourglass, Zeitgeist and more) for whom running their own tasting room would be either too time-consuming, too expensive, or both. Clients fill out a questionnaire first, after which Stevens will curate a selection of wines to taste. The space is utilitarian, but welcoming, with a long single table in the middle of a room decorated with artwork by local artist Layla Fanucci.

1299 Main Street

Family-owned and operated by the Leonardini family since 1993, this winery gives you the classic Napa Valley style tasting experience, from the walk-up bar positioned as you first enter to the tour of the winery and grounds provided with every tasting. You can go big and taste their portfolio-headlining Cabernets in a modern setting that overlooks the vineyard in back of the winery, or you can settle in and sip some Sauvignon Blanc al fresco in the recently added garden pavilion surrounded by vines.

1563 St. Helena Highway S.

Chef and owner Elliott Bell comes from the French Laundry family tree, where he spent a decade as executive sous chef. Bell renovated the former Cindy's Backstreet Kitchen space for Charlie's (named after his son). Its airy, whitewashed setting is both loved by locals and sought out by destination diners. Food here is American brasserie in feel, elevated by high quality farm-to-table ingredients, some of which are grown just up the road at Spring Mountain Vineyard. While the menu changes seasonally, staples such as the Little Gems salad, with sour cream and onion dressing tossed with salt and vinegar potato chips, and the double-fried chicken stay in place. The wine list features a hefty dose of California, but a European presence too, including an ample Champagne section. Charlie's is one of the few places in the valley that stays open with a late-night menu (9 p.m. to 11 p.m.). Expect to see other hospitality folks filing in for a caviar bump or dirty steak after their shifts end. If Bell isn't in the kitchen himself (he almost always is), he's volunteering his time as a member of the St. Helena fire department or toting his children around town with his wife, Katy.

1327 Railroad Avenue

Chef and owner Jude Wilmoth arguably created the model that Charlie's Elliott Bell has employed around the corner: elevated comfort food and hearty portions combined with a vibe of convivial familiarity. Opened in 2004, Cook is always filled with locals, though the staff will likely remember you on your second visit too. Cuisine here is frankly Italian-centric, with the eggplant parmesan with béchamel or cavatelli all'arrabbiata with house-made spicy sausage vying for signature dish honors. Don't overlook the daily risotto, pasta and soup specials. The bar gets busy starting right at 5 p.m. The small dining room and close-quarter seating in the back hums with a din during peak dinner service, throughout which you'll see people getting up to go talk to friends or colleagues at other tables. Come hungry, start with the house barrel-aged negroni and enjoy a St. Helena Cabernet as you take in the scene. Note: Only open Monday through Friday (lunch and dinner), and you will need a reservation.

1310 Main Street

Christopher Kostow's ode to live-fire cooking and the valley's smash burger cult favorite—worth grabbing shaded patio seating when the weather cooperates.

831 Charter Oak Avenue

Bruce Marder's upscale Italian counterpoint to the valley's rustic trattorias—think polished room, deep Italian wine list and hearty pastas.

1320 Main Street

Long Meadow Ranch's flagship table for wine-country cooking sourced from the estate—classic Napa hospitality on Main Street.

738 Main Street

The ahi burger, fries and shakes institution—essential roadside fuel between appointments.

933 Main Street

Restaurant at Harvest Inn with valley views; handy for guests bedding down on the property or anyone wanting a refined meal near the highway's north end.

1 Main Street

Philip Tessier's Michelin-starred flagship—book well in advance for the full tasting ritual; pair with Under-Study next door for daytime casual.

587 St. Helena Highway S.

Mark Shoemaker's Cal-Italian tasting menus inside Hyatt's Alila—four- and eight-course journeys in a historic Georgian Revival setting.

1915 Main Street

Originally called St. Helena Bakery before the name was changed to Model Bakery in the 1930s, this is a local institution. Former caterer Karen Mitchell purchased the business in 1984 and was joined by her daughter Sarah in 2011. Along the way, they've expanded the business to other locations, including downtown Napa. Expect a line in the morning, but if you're there early enough, you never know what winemaker might pass through on their way to work. There are few better places to carbo load and caffeine up for the day.

1357 Main Street

Where Hermes meets Willy Wonka is how chef and co-owner Philip Tessier describes his culinary playground. While his PRESS, next door, provides the Michelin-experience, this place evokes hedonism and whimsy, from the baked goods on display right as you walk in to the lobster omelette offered on weekends. You can also put together an elevated grab-and-go picnic, with the likes of jarred duck rillettes or charcoal-roasted beets. There's a butcher counter in the back and a demonstration kitchen. You can pick up a bottle of wine here, too.

587 St. Helena Highway S.

A tap house/coffee/snack/ice cream stop all in one. The campfire-flavor ice cream is a big draw.

1234 Main Street

Just off Main Street, this gelato/coffee house will satisfy any sweet tooth. Try the salted speculoos crunch.

1336 Oak Avenue

Old-school Main Street deli counter for sandwiches and picnic supplies before heading up-valley.

1227 Main Street

Neighborhood provisions and wine-country gifts a stone's throw from Ad Vivum and other west-side tastings.

1400 Oak Avenue

Coffee and light bites in a compact shop perfect for resetting between Main Street strolls.

1153 Main Street

Owner Rick Kaufman purchased Harvest Inn in 2013 and he's been tweaking and improving it ever since, including adding rooms and new dining facilities. Harvest Inn has a bit of a throwback feel, as its Tudor-style buildings that house the guest rooms feature brick work and leaded-glass windows. The 8-acre property meanders through towering redwoods that provide cool shade and a respite from the bustle of the highway. It also borders the Leonardini Vineyard of Whitehall Lane, affording some rooms picturesque views (and most rooms have a fireplace). There are family and adult-only pools on site. While Kaufman is a wine and cigar lover, he embraces the idea that the valley should provide a complete vacation experience; to wit, his concierge can arrange for pheasant hunting, clay shooting, horseback riding, hot-air balloon rides and more.

1 Main Street

This 12-room boutique hotel occupies the historic Kibbler building (1886). The location is perfect, catty corner from Model Bakery and steps from the main shopping and restaurant section of town. The comfy, well-appointed rooms are spacious, featuring high ceilings, unique furniture items and curated decor. The place feels both cozy and tony; owner Mark Hoffmeister describes it as feeling like you're in a cool apartment. Named after Wydown Boulevard in Hoffmeister's native St. Louis, the hotel provides breakfast and afternoon tea. Guests also have complimentary access to Health Spa Napa Valley. Carol, the head concierge, knows the lay of the land and will help set you up with tasting appointments and restaurant reservations.

1424 Main Street

A historic setting, Alila's main lobby is located in the property's original, 1907 Georgian Revival residence. By 1911, the site was home to St. Helena's first tourist resort and after more than a few iterations along the way, it's now Hyatt's Alila, a 69-room and suites, adult-focused property (under 18 must be accompanied by a parent at all times). The modern architecture that was added adheres to the symmetry of the original Acacia House. The main restaurant, Violetto, features four- and eight-course tasting menus for dinner, while the Salvia Terrace offers à la carte options and an elegant setting for golden hour. A full spa and swimming pool fill out the grounds. The spacious vineyard-view rooms have a terrace for sunset-watching, and there's direct access to Beringer Vineyards, right next door.

1915 Main Street

• Phone: (707) 963-5105

Originally a New Yorker, Dr. George Belden Crane purchased more than 300 acres of land in St. Helena on which he built his home and planted European grape varieties in the 1860s. His 1879 Victorian house is now part of the Salvestrin family's estate, operating as a three-bedroom B&B amid their holdings in the Dr. Crane Vineyard.

397 Main Street