Things to do in Healdsburg
Discover amazing Healdsburg activities and premium in-home experiences.
Healdsburg is a charming gem in the heart of Sonoma County’s wine country, where scenic vineyards meet a vibrant downtown brimming with boutique shops and farm-to-table eateries. Stroll historic streets, sip on award-winning vintages, and immerse yourself in a laid-back atmosphere that captures the true spirit of California living. Whether you’re a wine enthusiast, foodie, or weekend explorer, Healdsburg delivers an unforgettable blend of small-town charm and world-class experiences.
Popular Activities in Healdsburg
Healdsburg Bike Rentals for Wine Country Exploration
Pick up a quality bike with helmet and lock from the Healdsburg shop and explore at your own pace.
Healdsburg Sip 'N Cycle Wine Country Bike Tour
Cycle quiet back roads, visit two wineries, and enjoy a picnic with e-bikes and expert guides included
Calistoga Sip N' Cycle Bike and Wine Tour
Pedal quiet Calistoga backroads to two wineries with a picnic lunch included
The Rio Trip: Morning Paddle on the Russian River
Paddle a scenic 5-mile stretch with shuttle, swimming spots, and abundant wildlife
Gourmet Healdsburg Food, Wine & Cocktail Tour
Taste Healdsburg with up to 16 bites and sips across 5–6 stops, guided by a local expert
Healdsburg Wine Tour: Private Tour & Custom Itinerary
Embark on a curated 6-hour journey through the picturesque landscapes of Napa and Sonoma Valleys.
Sonoma County Gourmet Picnic with Private Chef
Escape into the beauty of Sonoma County with a curated picnic experience along the stunning Russian River or Sonoma Coast.
Russian River Kayaking with Shuttle Service
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.
Guided Sonoma Valley Hike with Champagne Toast
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.
Sonoma Wine Country Bike Tour with Tastings
Immerse yourself in the beauty of Sonoma with our Scenic Wine Country Bike Tour.
Small-Group Sonoma Wine Tasting Tour with Charcuterie
Relax while we handle the driving and visit three Sonoma wineries
Kendall-Jackson Food and Wine Pairing Experience
Enjoy a private 5-hour farm-to-table pairing at Kendall-Jackson plus a seated tasting at La Crema with pickup included
Large Group Customizable Private Tours
Craft your ideal wine country outing with included transport for groups up to 14
Small Group Customizable Private Tour in Sonoma County
Design your itinerary with included pickup, reservations help, and space for up to 8 guests
Sonoma Private Wine Tour with 3 Wineries
Travel in style as our expert guides whisk you away on a bespoke 6-hour tour of three hand-picked wineries.
8-Hour Private Fishing Charter in Bodega Bay
Embark on a memorable fishing adventure with our Private Bodega Bay Fishing Charter, designed to offer you an unrivaled fishing experience! Tailored to accommodate up to six people, this charter is perfect for families or a group of friends looking to create some memories while fishing.
Three-Hour Sailing Tour of Bodega Bay
Sail Bodega Bay for three hours and watch for sea lions, whales, and birds
50cm Trek Domane SL6 E-Tap Road Bike Rental
Ride a high-performance road bike with SRAM E-Tap to explore Napa Valley's scenic roads
In-Home Experiences
Celebration Cupcake Surprise
Whether you’re marking a birthday, anniversary, or simply enjoying a sweet moment, these cupcakes are sure to make your stay unforgettable.
Quintessential California Dining Experience
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.
In-Home Express Glow Facial in Santa Rosa
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.
In-Home Glow Group Facial in Santa Rosa CA
Level up your celebration with our In-Home Glow Group Facial—professional skincare, relaxation, and fun, all in the comfort of your rental.
In-Home Massage with Hot Stones & Spa Treatments
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.
Sommelier‑Led Wine Tasting Experience
Enjoy a private, sommelier-led wine tasting without leaving your stay.
Winemaker for a Day Experience
Craft your own custom wine blend in California wine country
Signature Cocktail Crafting Experience
Shake, stir, and sip your way through a private cocktail workshop at your rental
Blindfolded Sip Experience
Test your senses with a unique blindfolded wine tasting experience
Discover More in Healdsburg
Healdsburg isn’t just a pretty wine country town -- it’s an immersive destination where each turn reveals a new layer of discovery. Whether you’re here for a romantic weekend, a family getaway, or a solo retreat to recharge, Healdsburg delivers on depth, flavor, and experience.
Start your day with a slow coffee from a local roastery before venturing out on a guided e-bike tour through the Dry Creek Valley, where you’ll coast past olive groves, lavender fields, and centuries-old vines. Prefer something more hands-on? Join a farm tour and cooking class, where you’ll pick seasonal produce and turn it into a multi-course meal under the guidance of a local chef.
Downtown Healdsburg invites exploration with its blend of upscale boutiques, contemporary art galleries, and hidden gems like speakeasy-style tasting rooms tucked into alleyways. Around the plaza, Michelin-starred restaurants sit comfortably next to cozy cafes and wine bars serving small-lot vintages from just down the road.
For those seeking deeper connection to the land, Healdsburg offers a range of immersive experiences -- from forest bathing in the redwoods to private vineyard picnics, kayak excursions on the Russian River, and curated wellness retreats that blend wine, nature, and rest.
Whether you're planning a proposal, a girlfriends' getaway, or simply craving a weekend where everything feels just a bit more meaningful, Healdsburg delivers the perfect blend of luxury and authenticity. It's a place that invites you to slow down and savor, not just the wine -- but the moment.