Itinerary: Healdsburg, Sonoma - A 3-Day Wine-Packed Trip
Overview
Healdsburg is a charming town nestled in Sonoma County’s celebrated wine country, perfect for a laid-back yet fabulous getaway. Whether you’re a wine lover, a foodie, or just someone who appreciates beautiful places and experiences, this 3-day itinerary blends it all together.
We’ve done some version of this trip annually for several years. There are a lot of ways to plug and play the towns, wineries, and restaurants mentioned, but this version is one of our go-tos.
For a deeper dive into the all the spots, check out my Healdsburg Guide here.
Day 1: Arrival & Wine Tasting
10:30 AM – Land at SFO and Pick Up Rental Car
The drive from San Francisco International Airport (SFO) to Healdsburg takes about 1.5 hours. Consider grabbing lunch en route to save time - local favorites like Amy’s Drive Thru offer tasty, vegan-friendly options to fuel your first day.
1:30 PM – Winery #1: Gary Farrell
Start your wine tasting adventure at Gary Farrell. You’ll enjoy a tastings of their fantastic Pinot Noirs - a Sonoma classic. The setting here is stunning and the wines are consistently delicious.
3:00 PM – Winery #2: Williams Selyem
Next up, Williams Selyem. This winery is a bit of a gem and if you’re lucky enough to secure an appointment (member access helps), it’s well worth the visit for their elegant Pinots and intimate setting.
Other good winery options along this route are Aperture (gorgeous tasting room), Flowers Vineyards and Winery, and MacRostie Winery
5:30 PM – Check-In to Your Hotel
Options like h2hotel, Harmon House, Best Western Dry Creek Inn, or The Madrona provide comfortable bases with easy access to downtown Healdsburg’s charm.
6:00 PM – Dinner & Exploring Downtown
Stroll around downtown Healdsburg and enjoy dinner at one of several fantastic restaurants. Little Saint is a plant-based spot that is worth a stop, whether it’s for dinner, breakfast, or all meals. Other excellent choices include Matheson, Roof 106, Bravas Bar, and Chalkboard - all with a variety of vibes and menus to suit your mood. If you’re feeling fancy, check out Michelin Star restaurants like SingleThread or Cyrus, which is just north in Geyserville and especially noteworthy for Top Chef fans with Chef Douglas Keane at the helm.
Day 2: Bikes, Wineries & Picnic Lunch
8:00 AM – Breakfast at Plank or Little Saint
Plank is a great, quick stop for breakfast, with plenty of vegan-friendly options and a cozy, welcoming vibe. Little Saint is also a must-stop - I usually end up here multiple times a trip since they offer breakfast, lunch, and dinner.
9:00 AM – Pick Up E-Bikes
Book early with Getaway Adventures to snag e-bikes and explore Healdsburg and the surrounding vineyards with ease.
10:30 AM – Winery #3: Reeve
Kick off the day’s tastings at Reeve winery down the long, winding drive to get to the tucked-in tasting room surrounded by cutie farm animals and great vibes.
11:30 AM – Pick Up Lunch
Stop by Dry Creek General Store to pick up a picnic-friendly lunch - think hearty build-your-own sandwiches and fresh local produce.
12:00 PM – Winery #4: Dry Creek Vineyard
This winery isn’t the flashiest, but their Zinfandels are solid, and the picnic grounds make it a perfect lunch stop. Bonus: BYO lunch is allowed, so you can enjoy your Dry Creek General Store haul while sipping on some wine.
1:00 PM – Winery #5: A. Rafanelli
Visit A. Rafanelli for a classic Sonoma experience - they offer rich, balanced wines in a beautiful setting.
3:00 PM – Winery #6: Lambert Bridge
Finish your tasting day at Lambert Bridge for elegant, estate-driven wines in a refined but approachable setting.
Other good winery options along this route are Quivira Vineyards, a standout for organic and sustainable wines with lovely garden worth strolling through and Bella Winery, for its wine caves.
6:00 PM – Dinner in Healdsburg
Relax and unwind over dinner. See options from Day 1.
Day 3: More Wine & Local Flavors
9:00 AM – Breakfast at Plank or Little Saint
Try Plank for a quicker stop or linger over breakfast at Little Saint
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10:00 AM – Winery #7: Ridge Lytton Springs
Spend your morning at Ridge, known for its elegant Zinfandels and hillside views.
12:00 PM – Lunch & Tasting at Jordan Winery
Jordan offers an exceptional lunch paired with wine tasting - a real treat and perfect for a leisurely midday break. Depending on whether it’s on offer when you visit, the 3-hour Estate Tour & Tasting is the single best experience in Sonoma IMO. If you have the chance, I’d skip other wineries to make room for this one.
1:30 PM – Winery #8: Stonestreet
Known for Cabernet Sauvignons and beautifully manicured vineyards, Stonestreet offers lovely views and a welcoming, relaxed tasting experience.
3:30 PM – Winery #9: Silver Oak Alexander Valley
Wrap up your wine tastings at Silver Oak, a Sonoma staple with excellent Cabernet Sauvignons.
6:00 PM – Final Dinner & Exploring
Enjoy your last evening in Healdsburg with a nice dinner, perhaps revisiting a favorite spot or checking out a new restaurant.
Notes & Tips:
Tasting pace: I usually recommend 2–3 wineries per day, but the full days include a fourth stop because one of the wineries doubles as a lunch destination. Doing 3 total tasting, with either one being over lunch or paired with a non-wine lunch, would also work great.
Plant-based travelers: Healdsburg has a growing scene of vegan and plant-friendly dining, but many omnivore-friendly restaurants have great plant-based options too. Don’t hesitate to ask - most kitchens are happy to accommodate.
Booking wineries: Many tastings require appointments, especially for members. Book ahead to secure your spots.
Getting around: Renting a car is essential for getting to the region and useful for winery hopping, but you may want to consider a driver if you don’t want to designate a sober driver. The e-bikes will be your mode of transportation on Day 2 and are great for exploring locally in and around Healdsburg.
This is a pretty full itinerary, but it’s a great way to get a feel for Healdsburg and the surrounding wine regions in a short window. The overall shape works well - good wine, good food, beautiful scenery - with enough flexibility to swap in different wineries or restaurants depending on what you’re most excited about. Use it as a starting point and adjust from there.
Please share any recommendations or feedback. Cheers!
