This Charming Small Town in California Wine Country Is Straight out of a Nancy Meyers Movie

Sunset’s Insider Guide series highlights seasonal diversions and secret travel tips from local experts. Follow along as we learn where to eat, drink, stay, and shop.

Photo by Leigh Ann Beverley.

Meet the insider: Sam Bilbro, managing partner and winemaker at Overshine Wine Co.

Location: Healdsburg, California

While it’s true that there’s no shortage of great winemakers in Sonoma County, Sam Bilbro shines in his own light, focusing on producing unique and esoteric Italian varieties not often seen amid the classics. Bilbro, a fourth-generation winemaker and Valley local, shares some of his favorite spots to enjoy in his hometown when he’s not busy managing the crushpad or overseeing the ever-expanding brand.

STAY

Matthew Millman

While this might be a bit of insider trading, the Overshine Collective’s small B&B Casa Comunità is about as beautiful, homey, and quaint as you can get. Don’t sleep on its stunning breakfast spread with house-cured bacon and French pastries. If you’re in town for a fancy weekend, The Madrona is such an amazing property full of history and charm. If you like things a little more rustic, AutoCamp Sonoma in Guerneville is a can’t-miss spot. Located in the redwoods, it’s close to hiking, swimming spots, and all the best that nature has to offer.

EAT

Courtesy of John Troxell

Diavola Pizzeria in Geyserville has long been a favorite. The menu is always changing, and I love the casual feel mixed with all the amazing food. You can’t miss the Sonja pizza! Guiso Latin Fusion is a rarity in our town. Chef Carlos does an amazing job showcasing his heritage in an innovative way through his Latin fusion menu. Bonus: The spot is so small and intimate in the best of ways.

DRINK

Courtesy of Stay Healdsburg

Lo & Behold Bar + Kitchen in Healdsburg has fantastic cocktails, a great atmosphere, and an amazing team. The Geyserville Gun Club is my go-to spot for a drink and a great bite of food. I suggest a martini and the spicy tuna hand roll.

DO

Brian Lima/Sonoma County Tourism

Besides visiting wineries and eating your way around town, be sure to check out Little Saint for a concert, and on Saturdays, be sure to stop by the new location of the farmers’ market located across the street at the recently built Foley Family Community Pavilion. Afterward, enjoy a hike out at Lake Sonoma, and stop for a beer at Dry Creek on the way back in.