Trip Itinerary / Fun Guide from Healdsburg to Calistoga

There is so much to see, do, and experience in wine country. With so many small towns and unique spots scattered throughout Napa and Sonoma, there’s always somewhere new to explore – all it takes is the perfect itinerary. And while you can easily drive directly from Healdsburg to Calistoga, isn’t it so much more fun to discover an adventure or two along the way?

Our trip itinerary from Healdsburg to Calistoga takes you through a few of our favorite local spots, with fun pit stops that are sure to make a road trip to remember.

Ready to hit the road? Keep reading to start planning out your trip through wine country.

Healdsburg to Calistoga: The Perfect Itinerary

You’ve got a full tank of gas, your favorite road trip snacks, and the open highway in front of you: it’s time to head out for your trip from Healdsburg to Calistoga.

Planning the perfect itinerary can be tricky if you don’t know an area well, so leave the planning to us, turn on the road trip tunes, and enjoy the ride. We’ve crafted a guide to all of our favorite stops along the way for an adventure you’ll never forget.

Healdsburg

We’re starting off the journey in Healdsburg, California – a charming small town in the heart of Sonoma County. Nestled along the Russian River, Healdsburg is one of Sonoma’s top wine tasting destinations, as it’s home to several of the most iconic wine appellations in the area.

Before you hit the road, here are a few of our favorite spots in Healdsburg:

Enjoy a Pastry at Quail & Condor Bakery

The best road trips always begin with pastries, and you won’t be disappointed when you stop by Quail & Condor Bakery. Listed in The New York Times as one of the 22 best bakeries in the US, you’ll be obsessed with Quail & Condor’s baguettes, croissants, and seemingly endless baked goods. Trust us – you’ll want to order extra for the road.

Visit Healdsburg’s Historic Plaza

Located in downtown Healdsburg, you can’t miss a visit to the historic plaza. You’ll feel like you’ve wandered into a film as you explore the picturesque area lined with shops and restaurants. It’s the perfect place to pick up some handcrafted souvenirs for friends and family back home, and we always have to pop into an art gallery or two while we’re there to enjoy the stunning local works.

Explore the Healdsburg Museum & Historical Society

History buffs will want to be sure to stop by the Healdsburg Museum and Historical Society, located in a former Carnegie library. This museum is listed in the National Register of Historic Places, and is a fantastic resource for anyone wanting to learn more about Healdsburg and Sonoma at large. The museum features rotating exhibits, so there’s always something new to see every time you stop by – learn about Native American customs, local Healdsburg lore, and more. The museum and historical society is free to the public, so it’s a great place to add to your travel list!

Windsor

From Healdsburg, it’s time to head to Windsor – a beautiful, family-friendly Sonoma town that’s known for abundant outdoor space and a whole host of free community activities throughout the year. Be sure to do a little research to see if anything fun is going on while you’re in Windsor – they’re always up to something new!

Visit the Town Green

When visiting downtown Windsor, you won’t be able to miss the Town Green – a beautiful open green space for locals and visitors alike to play, picnic, and enjoy the California sunshine. Wander downtown and pick up a delicious snack or meal from one of the many restaurants in walking distance, then bring it over to the green to people-watch and enjoy the quaint sights of downtown Windsor. Or, if you happen to be in Windsor on a Sunday, stop by in the morning to see the Town Green transformed into a local farmer’s market!

Windsor Bike ‘N Beer Tour

While you’re probably visiting California for the world-class wine around every turn, did you know that there are amazing craft breweries locally as well? Ride through the Windsor countryside, taking in the sights as you enjoy the stunning Russian River region, visiting some of the best beer-related destinations along the way. It’s a fun way to see the area and explore!

Santa Rosa

Next up on our itinerary: a stop in Santa Rosa, California. One of the more popular wine country destinations, Santa Rosa has so much to do and see while still hanging on to that wine country charm that we all love so much. With a thriving downtown, vibrant cultural scene, and outdoor adventures galore, it’s worth taking the time to explore. Plus, if you visit on a Sunday morning, you’ll have the opportunity to wander the Santa Rosa Farmers Market – the largest Farmers Market in Sonoma County!

Visit the Charles M. Schulz Museum

Who doesn’t love Peanuts? A true Santa Rosa hidden gem, the Charles M. Schulz Museum is such a fun spot to visit. View galleries that showcase how the Peanuts characters have changed and developed over the years and see the beloved cartoon come to life before your eyes. Keep your eye out as you explore Santa Rosa – Schulz called the area home for the last 30 years of his life, and there are fun Peanuts-related easter eggs scattered throughout the area.

Go for a Hot Air Balloon Ride

The only thing better than the beauty of wine country? Taking in those stunning views from the sky. See the rolling hills and towering redwood trees from above and gain a bird’s-eye view of this breathtaking region. Trust us – it’s an experience you’ll never forget.

Calistoga

Welcome to Calistoga: home sweet home, and our (only slightly biased) favorite place in wine country. With an abundance of shopping, dining, and spa amenities, there’s nowhere like Calistoga to relax and unwind.

Visit the Petrified Forest

One of the most fascinating spots in Calistoga, explore breathtaking petrified redwood trees in the Petrified Forest. There’s nowhere like it – created upon the explosion of a volcano millions of years ago, this beautiful grove was perfectly preserved and remains an incredible destination to visit.

Relax in the Hot Springs

Calistoga is famous for its abundant hot springs, which were thought by the natives to have magical healing qualities. The therapeutic effects of the springs are undeniable – providing deep relaxation, improving circulation, and alleviating tension and pain. Hot springs experiences are found all over Calistoga, and you’re sure to be amazed by how great you feel after experiencing them for yourself.

Conclude Your Journey With a Visit to Davis Estates

Of course, no visit to Calistoga is complete without concluding your journey with a visit to Davis Estates – the finest winery in the Napa Valley.

We offer daily tastings and tours, whether you want to explore our wine cellars or take in panoramic views of the valley from our beautiful terrace. Sip and savor as you taste your way through our array of Cabernet Sauvignon wines, or sample a variety of reds and whites for a holistic tasting experience at the Estate Wine and Food Pairing.

Experiences are available by reservation only – secure your spot today.