Healdsburg is an ideal destination for a short vacation or long weekend getaway. Just a few hours’ drive from some of California’s top cities brings you to this serene setting of Wine Country, where you’ll find beautiful vineyards, charming towns, and an atmosphere that makes it easy to unwind. Here’s our ideal three-day itinerary for a weekend getaway to Healdsburg:
Itinerary at a Glance
- Day 1: Arrival
- Day 2: Adventuring in Sonoma County
- Day 3: Soak Up Some Extra R&R
Day 1: Welcome to Sonoma County
Check into Your Healdsburg Vacation Rental with WC Lodging
Our Northern California vacation rentals allow for check-in at 3:00 PM. Unpack your bags, get settled, and then head to downtown Healdsburg for a stroll. Several of our Healdsburg vacation rentals are within walking distance to Healdsburg Plaza, so you’ll find it’s one of the best ways to stretch your legs after a long drive or flight.
WC Lodging Tip: Consider adding on our Concierge Service(available for select properties) when you book directly with WC Lodging. Add-ons include full-service grocery shopping and stocking, a charcuterie and wine welcome package, itinerary and activity planning, and household and comfort add-ons.
Dinner at Bravas Bar de Tapas
Considered one of the top 20 tapas bars in the US, Bravas is a must-visit during your Healdsburg getaway! Expect traditional Spanish and Spanish-inspired tapas and large plates, like paella. Reservations are recommended on the weekends.
For a quick and easy dinner, put in a to-go order at PizZando. Serving Napolitana and Romana-style pizzas, house-made pastas, and more, there is something for everyone on the menu. Pick it up, take it back to the rental, and turn on a movie for a cozy, restful night in.
Day 2: Adventuring In and Around Healdsburg
Day 2 is all about adventuring and exploring all that Healdsburg has to offer!
Hot Air Balloon Ride with Sonoma Ballooning
The day starts very early as your hot air balloon ride with Sonoma Ballooning takes flight at sunrise. Enjoy a 45-60 minute ride and take in the calmness of a morning in the sky. Flights come with pre-flight refreshments and a celebratory champagne toast post-flight.
Coffee & Light Bites at Quail & Condor
While you’ll get refreshments and light snacks with Sonoma Ballooning, treat yourself to a more hearty breakfast and delicious coffee at Quail & Condor. You can’t go wrong with an almond croissant or a parm onion biscuit. If you’re hungry, Quail & Condor’s breakfast menu includes items like a Turkish breakfast, veggie quiche, sourdough waffles, bagels, and toast.
Visit Orsi Family Vineyards
From Sangiovese to Schioppettino, experience a taste of Italy right here in Sonoma County. Just minutes from downtown Healdsburg, Orsi offers an intimate, serene setting where guests can savor limited-production wines crafted with exceptional care. The tasting room is open Thursday through Sunday from 10:30 AM – 4:30 PM (reservations recommended).
WC Lodging Tip: 🍷 Enjoy a complimentary tasting for up to 6 guests at the acclaimed Orsi Family Vineyards when you book with WC Lodging.* ($210 total value)
Dinner at Willi’s Seafood & Raw Bar
Book a table at Willi’s Seafood & Raw Bar for a blend of East Coast flavors and South American flair. Dive into New England-style rolls, a wide selection of raw oysters, and other seafood dishes. While mainly a seafood joint, there are a few options like crispy pork belly tacos, chicken, and steak available.
Day 3: Soak Up Some R&R
Day 3 is about slowing down and appreciating the stillness and beauty of Wine Country.
Yoga with The Yoga Van
Start your morning off with the Yoga Van – a mobile yoga and wellbeing studio designed to bring the essence of Wine Country Wellbeing into the most beautiful pockets of Sonoma and Napa Counties. The best part is that they’ll come right to your Healdsburg vacation rental, so all you’ll have to do is roll out of bed and meet them on the mat.
Breakfast at Acorn Cafe
After a zen morning with The Yoga Van, head to Acorn Cafe, where you’ll find a menu with everything you can think of. Fresh juices, classics like avocado toast and eggs Benedict, and Acorn specialties like lemon ricotta hotcakes and tiramisu French toast.
Visit Rancho Maria Winery
Next on the list is a visit to Rancho Maria Winery in Geyserville. Join Sebastian Juarez for a private tour & tasting at the family vineyard and experience a detailed journey through our 10-acre Dry Creek Valley estate, where Sebastian will guide you from grape to glass.
Go for a Dip in the Pool or Hot Tub Soak at Your Vacation Rental
After your winery visit, it’s time to head back home and take advantage of your Sonoma County vacation rental amenities. Several of our Healdsburg vacation rentals offer the choice of a private pool, private hot tub, or both! Make the most of your stay and utilize these luxurious amenities. If you’re visiting during the summer, a refreshing dip in the pool is a must, or if you’re visiting in the cooler months, a hot tub soak with a glass of local wine is the way to go.
Dinner at Single Thread
Experience Michelin-star dining at Single Thread in Healdsburg and make the last night of your Healdsburg vacation one to remember. That’s because chef Kyle Connaughton and head farmer Katina Connaughton have put together a one-of-a-kind experience that includes a 10-course Kaiseki-style menu that draws largely from the restaurant’s lush 24-acre farm in Dry Creek Valley.
WC Lodging Tip: Seatings at Single Thread are in very high demand, so we recommend booking in advance.