The Perfect Healdsburg Bed & Breakfast Weekend Itinerary
Nestled in the heart of Sonoma County wine country, Healdsburg is the perfect blend of small-town charm (it’s kind of like a Hallmark movie here!) and unique wine experiences. Whether you're seeking romantic vineyard views, local wines, or simply a peaceful retreat in wine country, Healdsburg always delivers.
Here's how to make the most of your Healdsburg weekend getaway with the perfect combination of rest, exploration, and wine tasting.
Where to Stay: Make a Healdsburg Bed and Breakfast Your Home Base
Begin your weekend at Casa Comunita, our serene Healdsburg bed and breakfast set on six lush acres. It’s intimate yet spacious—a place where modern comfort meets wine country hospitality. Wake up to a complimentary breakfast and freshly brewed coffee served next to the garden and take in a peaceful morning before going wine tasting in Healdsburg.
One major perk of staying at Casa Comunita? Guests receive complimentary tastings at two Overshine Collective wineries, giving you a built-in start to your weekend wine adventure.
Friday Evening: Arrive and Wander Downtown
Check in at Casa Comunita in the late afternoon, giving yourself time to settle into your room for a refresh, and then head to Healdsburg Plaza for an evening stroll. The town square, surrounded by boutique shops, two adorable bookstores, galleries, and restaurants, offers a charming introduction to the area.
For dinner, explore one of the plaza's celebrated restaurants. The Healdsburg food scene punches well above its weight, with options ranging from farm-to-table California cuisine to one of the world’s 50 Best Restaurants, SingleThread. After dinner, take a leisurely walk around the plaza to soak in the small-town atmosphere before returning to your suite at the bed and breakfast for a restful night's sleep.
Not quite ready for bed? Swing by the Martha Stoumen tasting room (one of Healdsburg’s newest wine tasting rooms) for a glass of wine after dinner. They stay open until 9pm on Fridays and Saturdays.
Saturday Morning: A Garden Breakfast or Go into Town
Start with a leisurely breakfast in the garden at Casa Comunita, or head into town for the iconic pastries at Quail & Condor, praised by the New York Times as one of the Best Bakeries in the US!
Saturday Afternoon: Vineyards + Vinyl at Overshine Wines
In the afternoon, make your way to Overshine Wines, the flagship of the Overshine Collective. Walking into Overshine feels like showing up at your cool cousin's house for an afternoon of sipping wines, listening to vinyl records, and taking in one of the best winery views in Sonoma County.
The vibe here is relaxed and welcoming, with a focus on wines that reflect California's soul—vibrant, diverse, and meant to bring people together. Browse the impressive record collection, settle in to your tasting, and let the staff (who genuinely feel like friends) guide you through the lineup.
Saturday Late Afternoon: Downtown Tasting at Comunità + Idlewild
Before returning to Casa Comunita, stop by the Comunità + Idlewild shared tasting room downtown. It’s equal parts wine bar, Italian inspiration, and casual hangout — an easygoing complement to your earlier vineyard visit.
Idlewild Wines highlights Piedmontese varieties like Nebbiolo, Barbera, Dolcetto, Arneis, and more, grown in the high-elevation hills of Mendocino or at Las Cimas.
Comunità Wines focuses solely on wines from Las Cimas Vineyard, offering modern takes on Northern Italian grapes. Expect aromatic white blends (Kerner, Ribolla Gialla, Malvasia) and energetic reds (Refosco, Schioppettino, and the beloved light red Poor Scholar, (a blend of Schaiva, Refosco, and Teraldego).
Both brands offer a chance to explore northern Italy's lesser-known varieties without leaving downtown Healdsburg.
Saturday Evening: Dinner + Plaza Glow
After a full day of Healdsburg wineries, you've earned a spectacular dinner. From Spanish food at Bravas, to the trendy Matheson, our concierge can help you make reservations at one of the town's restaurants. After dinner, take an evening stroll around the illuminated plaza - its pure magic at night.
Sunday: Slow Breakfast + Martha Stoumen Wines
Savor a final garden breakfast at Casa Comunita, then head to Martha Stoumen Wines for an intimate, thoughtful tasting. Martha’s wines are known for their minimal-intervention approach, purity of fruit, and captivating textures.
Our Martha Stoumen tasting room is one of Healdsburg newest wine tasting rooms, and it’s quickly becoming a local favorite.
Sunday Afternoon: A Last Wander + Departure
Before checking out of our Healdsburg bed and breakfast, take one final walk through downtown. Browse the boutiques, and be sure to stop by one of the local independent bookstores for something to read on the plane ride home.
Local Tips for Your Healdsburg Weekend
Book tastings in advance: While many Healdsburg wine tasting rooms welcome walk-ins, it’s always best to make a reservation, especially on weekends. Casa Comunita’s concierge can help you book your spots at Overshine, Reeve, and Martha Stoumen as soon as you confirm your bed and breakfast reservation.
Pace yourself: With complimentary tastings at two Overshine Collective wineries included in your stay, you can afford to be selective about additional tastings. A good rule of thumb is to stick to no more than 2 tastings per day.
Embrace the weather: Healdsburg is beautiful year-round, but each season offers something different. Summer brings warm days perfect for patio tastings, while winter offers cozy fireplace settings and fewer crowds.
Explore beyond wine: While Healdsburg wineries are the main draw, don't miss the town's art galleries, shops, and the Russian River for kayaking or hiking.
Ask questions: Winemakers and tasting room staff in Healdsburg are passionate about what they do. Don't be shy about asking about vineyard practices, winemaking techniques, or food pairing suggestions.
Buy at the source: Many small producers like those in the Overshine Collective have limited distribution. If you love a wine, purchase it at the tasting room, as certain bottles can be hard to find elsewhere.
