Best 30 things to do in Healdsburg, CA

Pick up a quality bike with helmet and lock from the Healdsburg shop and explore at your own pace.

Sip and cycle Dry Creek Valley with guided winery stops and a picnic lunch

Pick up a road or hybrid bike in Healdsburg and ride Wine Country your way

Bike Calistoga backroads to two wineries, with a picnic lunch

Paddle the Russian River and enjoy a picnic lunch at Wohler Bridge

Paddle a calm 5-mile Russian River stretch with an easy shuttle upstream

Taste your way through Healdsburg with food, wine, and a cocktail

Embark on a curated 6-hour journey through the picturesque landscapes of Napa and Sonoma Valleys.

Whether you’re marking a birthday, anniversary, or simply enjoying a sweet moment, these cupcakes are sure to make your stay unforgettable.

Delight in the flavors of the California Central Coast with a gourmet dining experience in the comfort of your vacation rental. Our expertly crafted menu celebrates the region's legendary recipes and fresh, local ingredients. Each dish offers a taste of California's culinary heritage, perfect for any special occasion.

Escape into the beauty of Sonoma County with a curated picnic experience along the stunning Russian River or Sonoma Coast.

Perfect for those looking to unwind or seeking a gentle thrill, our self-guided kayak package is the ideal way to explore the serene beauty of the Russian River.

Join us as we hike around the beautiful Sonoma Valley, exploring its picturesque trails and breathtaking landscapes. Led by a local expert, this guided tour offers a perfect mix of adventure and relaxation.

Small-group Sonoma wine tasting with pick-up, drop-off, and charcuterie

Private 5-hour Kendall-Jackson pairing plus La Crema seated tasting

Build a private Sonoma County itinerary for up to 14 guests

Build your own Sonoma County private tour with pickup and a 5–10 hour charter

Travel in style as our expert guides whisk you away on a bespoke 6-hour tour of three hand-picked wineries.

Glow on the go! Our In-Home Express Facials bring pro skincare to your rental—choose a 30-min refresh or 75 minutes deluxe session for any occasion.

Level up your celebration with our In-Home Glow Group Facial—professional skincare, relaxation, and fun, all in the comfort of your rental.

Elevate your stay with our In-Home Spa Massage Experience, designed to bring the luxury of a full-service spa directly to your vacation rental. Enjoy a 60-minute massage session enhanced with hot stones, a refreshing peppermint head massage, and a pampering hand and foot scrub treatment, all delivered by our experienced team of massage therapists.

Enjoy a private, sommelier-led wine tasting without leaving your stay.

Craft your own custom wine blend in California wine country

Shake, stir, and sip your way through a private cocktail workshop at your rental