Healdsburg, California

The wine-country weekend for couples who would rather walk between tastings than drive. Restaurants, tasting rooms, galleries and shops ring the town plaza, and three wine regions meet here: Alexander Valley, Dry Creek Valley and Russian River Valley. That makes it an easy alternative to Napa, with the same grape-and-dinner rhythm in a smaller, more walkable town. Dinner can be as simple or as grand as you like: SingleThread, the farm restaurant and inn in town, kept its three Michelin stars in 2026, while plenty of tables around the plaza cost far less.