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Healdsburg, a charming town nestled in the heart of Sonoma County, invites you to spend a delightful weekend exploring its treasures. Whether the sun is shining or raindrops are falling, Healdsburg promises an unforgettable experience during your winter retreat. 

No matter if you’re a foodie, an art lover, a music enthusiast, or a wine connoisseur, Healdsburg offers a diverse range of activities to suit every taste. Let’s dive into a detailed itinerary that will make your weekend in Healdsburg truly special.

Friday FuN

Kickstart your weekend by venturing into town on Friday, where an assortment of enchanting activities awaits.

Experience Culinary Excellence at Molti Amici

Indulge your taste buds with a slice of perfection at Molti Amici, where the Margherita pizza reigns supreme. The aromatic blend of fresh ingredients will set the tone for a weekend filled with culinary delights.

Unwind with Complimentary Live Music in the Heart of Town

As the evening unfolds, head to Hotel Healdsburg, the heartbeat of the town. Immerse yourself in the rhythmic tunes of FREE live music, serenading the air with a melodic ambiance.

Coyote Comedy Night – Where Laughter Takes Center Stage

If laughter is what you seek, join the merriment at Coyote Sonoma’s Comedy Night for an evening of pure entertainment.

Saturday Exploration

Awaken on Saturday to the aroma of freshly brewed coffee and the promise of a day filled with exploration.

Artisanal Awakening at Troubadour Bread

Begin your morning at Troubadour Bread, where coffee and sandwiches offer the perfect fuel for a day of adventure.

Explore Healdsburg’s Shopping Haven on the Plaza

Dive into the heart of Healdsburg by strolling through its downtown, where local shops beckon with unique treasures.

Galleries, Jazz, and Inspiration Await

For art enthusiasts, the town boasts incredible galleries showcasing a diverse range of artistic expressions. Don’t miss the chance to visit Healdsburg Library and witness the magic of Ben Levin, presented by Healdsburg Jazz.

Sip & Savor – Wine Tasting Along Healdsburg’s Plaza and Beyond

As your weekend draws to a close, take a leisurely stroll along the plaza and indulge in some wine tasting. Healdsburg’s wineries offer a diverse selection of wines, each with its own unique charm and flavor profile. Enjoy the rich aromas and exquisite tastes as you sample some of the region’s finest wines, completing your weekend retreat with a toast to unforgettable memories.

Or, if you’re staying at Hotel Trio, elevate your experience with their convenient shuttle service. Explore the acclaimed wineries along the Dry Creek Valley Route or venture to Bacchus Landing for an immersive tasting experience.

Sunday Serenity

Before bidding farewell to Healdsburg on Sunday, take the opportunity to unwind and embrace the tranquility of the morning.

Relaxing Morning at Little Saint Healdsburg

Savor a cozy morning at Little Saint Healdsburg. Let the warmth of the surroundings and the inviting ambiance set the stage for reflections on the wonderful weekend you’ve experienced. Be sure to try one of their delightful cozy coffee cocktails, perfect for a chilly day, adding an extra touch of warmth to your farewell.

Embrace Winter’s Charm for Unforgettable Weekend Escape

Healdsburg, with its blend of culinary delights, cultural experiences, and scenic beauty, stands as a beacon for weekend getaways. Rain or shine, the town welcomes you to immerse yourself in a tapestry of flavors, sounds, and sights. Plan your next weekend getaway to Healdsburg, and let the memories of a perfect weekend linger long after you’ve left.