Our Favorite Hidden Gems, Wine Spots, & Must-Do Adventures

Welcome to Healdsburg, California—our absolute favorite spot in Wine Country! 🍷✨ If you’re dreaming of a weekend filled with amazing wine, incredible food, and beautiful scenery, you’re in the right place.

This guide is packed with all our best tips, hidden gems, and everything you WON’T find on Google—because we’ve spent years exploring Wine Country and Healdsburg is hands-down our favorite spot in all of Sonoma & Napa!

Why Healdsburg?

Healdsburg is a quaint, charming town with a mom-and-pop feel that sets it apart from Napa. It’s the perfect mix of laid-back vibes, top-notch food, and world-class Pinot Noir.
✔ Easy to explore on foot (especially around the Healdsburg Square!)
✔ Amazing wineries specializing in Pinot Noir & Chardonnay
✔ Tons of great restaurants, wine bars, and tasting rooms
✔ Access to epic outdoor adventures like scenic coastal drives & kayaking the Russian River

Where to Stay

If you want to be right in the action, stay near the Healdsburg Square so you can walk to wine tastings and restaurants!

Hidden Gem Spot: Fairview Inn & Suites
74 Healdsburg Ave, Healdsburg, CA 95448
Phone: 707-433-5548

This spot is super basic but has the BEST location—just steps from everything! We only found it by being there (it’s NOT the googles), and it’s a much more affordable option compared to the expensive hotels around the square.

Where to Eat (AKA Where to Have the Best Meals of Your Life!)

Healdsburg is a foodie’s dream. These are our absolute go-to spots for delicious meals:

✔ Healdsburg Bar & Grill – Perfect for a casual outdoor lunch & drinks.
✔ Roof 106 – A rooftop bar with small plates, great cocktails, and a fun vibe.
✔ Barn Diva – Delicious farm-to-table food with an amazing outdoor space.
✔ Bravas Bar De Tapas – Spanish-inspired tapas & next-level paella!
✔ Willi’s Wine Bar – Small plates & an awesome wine selection.
✔ Willi’s Seafood & Raw Bar – Amazing oysters & fresh seafood small plates.

Where to Drink Wine on the Square

One of the BEST things about Healdsburg? You don’t have to leave town to do wine tastings. There are tons of tasting rooms right on the square!

Important Tip:
Wine tasting rooms close early! Most shut down around 5-6 PM, so plan accordingly.

Our favorite spots for tasting right in town:

✔ Roadhouse Winery – Our absolute fave! Laid-back vibe, incredible small-batch Pinot Noir.
✔ La Crema – A fun and stylish tasting room with great wines.

Wineries You HAVE to Visit

If you want to experience the best wineries, head out to Dry Creek Road—it’s where all the magic happens.

Pro Tip:
Hire a driver or book a tour so you can fully enjoy the wine without worrying about driving.

These wineries are our absolute favorites (great wine, epic vibes, and stunning outdoor spaces):

✔ Bella Winery – Has cool wine caves to explore.
✔ J Vineyards – Known for amazing wine & sparkling wines.
✔ Roadhouse Winery – Our favorite for next-level Pinot Noir.
✔ La Crema – Iconic winery with beautiful tasting experiences.

Fun Things to Do in Healdsburg

There’s SO much more to Healdsburg than just wine! Here are some of our favorite non-wine activities:

✔ Drive to the Coast – Our favorite thing to do!

Route:
Stop at Howard’s Cafe for breakfast → Drive through Bodega Bay → Head up the Pacific Coast Highway to Jenner.

✔ Explore Jenner – Where the Russian River meets the Pacific Ocean. 🌊
✔ Cafe Aquatica – Cute spot right on the river for coffee & relaxing.
✔ Go Kayaking on the Russian River – Perfect if you want an active adventure.
✔ Take a Food & Wine Tour – Check out Savor Healdsburg for an epic local experience!

Bonus Tips for Smarter Travel!

Getting There: Best Ways to Get to Healdsburg

✔ Fly into San Francisco (SFO) or Oakland (OAK) – Both are about 1.5-2 hours from Healdsburg.
✔ Fly into Santa Rosa (STS) – A smaller airport just 15 minutes from Healdsburg!
✔ Drive from San Francisco – Take the scenic route over the Golden Gate Bridge & through Wine Country.

Fun Facts About Healdsburg & Wine Country

✔ Sonoma’s specialty? Pinot Noir & Chardonnay—especially from Russian River Valley & Sonoma Coast.
✔ Best time to visit? Fall (Sept–Nov) is harvest season—perfect for wine tastings & epic fall colors!
✔ Healdsburg Square = Wine Lover’s Dream – So many tasting rooms, you can sip your way through town!
✔ Pacific Coast Adventures – Healdsburg is just an hour from the coast, making it perfect for a wine + ocean trip combo!

How to Get Around Healdsburg

Walking – The Best Way to Explore Downtown

If you’re staying near Healdsburg Plaza, you won’t need a car to explore the town! Downtown Healdsburg is very walkable, with amazing restaurants, wine tasting rooms, boutique shops, and cafés all within a few blocks.
✅ Great for: Exploring downtown, wine tasting rooms, and cute local spots.
✅ No need for parking hassles if you’re staying in the heart of town!

Renting a Car – Best for Winery Hopping & Day Trips

If you plan to visit wineries outside of town, go on scenic drives, or take day trips to nearby vineyards, renting a car is your best bet.
✅ Best for: Exploring Sonoma wine country, Russian River Valley, and scenic drives.
✅ Parking is easy (most wineries and hotels have free parking).
🚫 Downside: You’ll need a designated driver if you plan on wine tasting all day.

Uber & Lyft – Limited Availability

Uber and Lyft do exist in Healdsburg, but availability can be spotty, especially in the evenings or outside of town. If you’re relying on rideshares, expect longer wait times and higher prices than in a big city.
✅ Good for: Short trips within town, getting back to your hotel after wine tasting.
🚫 Not reliable for: Winery hopping—there may not be a ride available when you need one.

Wine Tours & Private Drivers – The Best for Wine Tasting

If you’re planning a full day of wine tasting, the best way to do it safely and stress-free is by booking a wine tour or a private driver.

Options:

✅ Healdsburg Wine Tours – Custom private wine tours with a driver.
✅ Pure Luxury Transportation – Chauffeured wine tours with set itineraries.
✅ Designated Driver Services – Some companies drive your rental car for you so you can enjoy the day worry-free.

Bike Rentals – A Fun & Scenic Option!

Healdsburg is bike-friendly, and there are some gorgeous rides through wine country! You can rent bikes (regular or e-bikes) and cruise between wineries at your own pace.

Where to rent:

✅ Spoke Folk Cyclery – Classic & e-bike rentals.
✅ Wine Country Bikes – Self-guided or guided bike tours to wineries.

Final Thoughts: The Ultimate Healdsburg Experience

✨ Drink world-class wine
✨ Eat incredible food
✨ Take in the stunning scenery
✨ Explore beyond the vineyards

Whether you’re here for a weekend or planning a longer trip, Healdsburg is pure magic.

👉 DM us @Kimanderrang & tell us: What’s your favorite wine country experience? 🍷🔥