Lo & Behold Bar + Kitchen

Nestled on 258 serene vineyard acres with stunning NorCal-modern bungalows, Montage Healdsburg blends luxe comfort, local cuisine, and rustic charm.

Molti Amici serves fresh handmade pastas and wood-fired Neapolitan pizzas in a breezy, bocce-lined patio that screams casual Italian cool.

SingleThread in Healdsburg melds three-Michelin-starred kaiseki elegance with Sonoma’s seasonal bounty, served in a luxe inn inspired by Japanese ryokan hospitality.

Healdsburg's Matheson serves refined farm-to-table California fare with standout seasonal dishes and an epic 88-wine self-serve wall—all in a sleek three-level space.

At Portalupi Winery in Healdsburg, sip expertly crafted Cal-Ital wines in a cozy tasting room where the friendly staff makes every visit feel like family.

Chalkboard offers stylish seasonal American small plates and local wines in a cozy, inviting atmosphere perfect for unwinding after a day of wine tasting in Healdsburg.

This chic boutique hotel blends modern design with local art, offering spacious rooms with balconies, a rooftop bar, pool, and central Healdsburg location.

Since 1881, this bustling market serves gourmet sandwiches, salads, local wines, and picnic-friendly bites in a charming, laid-back setting.

Luxe downtown Healdsburg spot mixing modern minimalism, spa bliss, a heated olive-tree pool, and chef-driven wine country dining.

KINSmoke serves up hearty, craveable BBQ with Southern sides in a casual, rustic spot that's perfect for chilling after wine tasting.