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Add a little holiday magic to your meal with Pizzando’s whimsical Christmas Tree Affogato—creamy Strauss organic vanilla soft-serve topped tableside with a shot of freshly pulled Italian espresso and a shower of colorful holiday sparkles. Watch your server trim your

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Bring a little extra sparkle to your holiday outing with Pizzando restaurant’s festive pairing: Mozzarella in Carrozza—crispy, mini, golden-fried mozzarella and anchovy sandwiches—served with a glass of fine Italian bubbly by Bisol, a Prosecco Superiore DOCG. A warm, cheerful treat

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Make the season sparkle at Montage Healdsburg, where the mistletoe is waiting for your picture-perfect holiday moment. Throughout December, gather loved ones, steal a kiss, and capture the joy of the season beneath this festive tradition. Share your snapshots using

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Before Santa makes his stop in wine country, Montage Healdsburg invites guests to share their holiday wishes the old-fashioned way. Little ones can pen heartfelt letters and slip them into the festive North Pole mailbox in the hotel lobby. Whether

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Throughout December, young guests at Montage Healdsburg can experience the magic of the season at Santa’s Workshop, a festive activity at the Paintbox. Children will decorate gingerbread houses, craft personalized ornaments, and flex their holiday creativity. LEARN MORE

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Hotel Healdsburg guests will enjoy complimentary gift wrapping by hotel staff, ensuring your treasures are beautifully packaged and ready to share. Shop your way through art galleries, imaginative jewelers, stylish boutiques, locally owned bookstores, toy shops, and more—and leave the

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Fall Foliage Hikes Hike the Valley this Harvest Season WITH KAREN AUSTIN LOCAL TRAIL GUIDE AND CERTIFIED HEALTH COACH Immerse yourself in the golden glow of fall in Sonoma Wine Country with a guided fall hike through the rolling hills

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En Plein Air: Vineyard Painting Class WITH NELLA RUBINSTIEN FOUNDER OF HEALDSBURG ART ATELIER Experience the beauty of Sonoma County en plein air(French for “in the open air”) with an intimate, outdoor painting class set in the scenic vineyards of

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Hands-On Harvest Adventure A Front-Row Seat to Wine Country’s Most Magical Season WITH ZIALENA WINERY Step into the sensory spectacle of Sonoma County’s grape harvest season. Hotel Healdsburg invites you to experience this extraordinary time firsthand through our Hands-on Harvest

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Day Drift Kayaking Tour WITH GETAWAY ADVENTURES & HARMON GUEST HOUSE Trade the rush of daily life for a slow-moving river and the company of tall trees. This guided kayaking experience invites you and your crew—be it family, friends, or

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Harvest In Wine Country: A luxurious Getaway at Camelia Inn with Diane Wilson & Wilson Winery OCTOBER 2 – 5, 2025 Escape to the heart of Sonoma County this summer for an unforgettable long Wilson Artisan weekend of wine, food

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Harvest Retreat at Calderwood Inn September 14-16, 2025 A Luxurious Getaway at the Calderwood Inn Hosted by Winemaker Chris Barrett of St. Anne’s Crossing & Pezzi King Wineries Escape to the heart of Sonoma County this harvest season for an