Exploring Healdsburg, California Wine Country's Best Kept Secret

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Advisor - Lindsay Rawitscher
Curated By

Lindsay Rawitscher

  • Domestic Travel

  • USA

  • California

  • Food & Wine

  • Luxury Travel

  • High-end

  • Relaxation

  • Vineyard

Sunrise in the wine country.
Curator’s statement

Healdsburg is the hidden gem of Sonoma County, with many incredible vineyards and a fabulous town square lined with restaurants and tasting rooms. Typically, wineries here have more availability and often have special meal and tasting menu pairings. The town and surrounding areas are also stunningly green. There is a strong eco-focus put forth by every hotel in the area to preserve the natural beauty of wine country. At night, you can sip wine and make s'mores on one of the many rooftop lounges in town while stargazing.

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Day 1: Arrive & Check Out Town

White and rose bubbly wine.

Watch Sunset & Sip Wine

Arrive in Healdsburg around 5pm (by car from any bay area city/airport or by flying directly into Santa Rosa STS) so that you have time to settle into your room and change for the evening. Head over to Scout Field Bar in the hotel lobby for a perfect view of sunset and some incredible cocktails.

Dinner in the Square

After drinks, take a complimentary shuttle downtown for dinner at Bravas. After dinner, walk over to the Matheson for wine, dessert or just a nice view. The square is adorably lit at night, so feel free to walk around and enjoy the evening.

Day 2: Wine Country Day

A girl with polished boots sitting at a winery.

Archery Lesson

Wake up early and head over to the bike center to begin your complimentary archery lesson! The guides are incredibly patient and helpful; you can have up to 4 people shooting at one time. After your lesson, head back to the room and get ready for a big day of wine tasting!


Head to Robert Young Estate Winery for an 11 am tasting reservation. Pricing varies but this location is quite reasonable and will comp a tasting if you buy any wine. They have a lovely outdoor tasting room too.

Next, head to Willi's | Seafood & Raw Bar for a 1 pm lunch. Everything is incredibly fresh and there are lots of options for non-fish eaters.

Wrap up a day of vineyards with one of the most scenic in the area: Ridge Vineyards. Head in for a 3:30 pm tasting and enjoy your secluded, comfy couch as you look out across the vines before heading back to the hotel.

Under the Stars

Give yourself time to relax and freshen up before a phenomenal dinner at Hazel Hill, the onsite restaurant of the Montage. This coursed menu will run about $150 per person, or $200 with wine pairings. They are very accommodating to any dietary restriction and are also happy to substitute seasonal flavors for traditional menu items at your request.

Finally, wrap up the night with some star gazing, a unique experience hosted by the Montage. You'll go from the restaurant, past the lobby and into the entrance to the vineyards (or ask the concierge for guidance) to find an elderly gentleman and his daughter polishing their 5' brass and gold telescope. They will guide you along various constellations, teach you about some of the stories behind the stars and allow you to view space through their telescope.

Day 3: Brunch & Relaxation

Rolling vineyards in Sonoma Valley.

Wine & Brunch

Wake up at your leisure and head to Capo Creek, an incredible boutique winery and restaurant. You'll have a 2-hour brunch tasting menu paired with wines and hear about the life story of Mary, the owner, and her many dogs.


After brunch, head back to the hotel and take advantage of the pool, spa and other amazing hotel amenities. You can also explore the expansive property by foot or golf cart to see the spaces deep in the vineyards.


For dinner on your final night, head into town using the hotel's shuttle service. For something more low-key, make a reservation at The Taste of Tea, a charming tea shop and restaurant. If you want to have a more upscale experience, visit Harmon Guest House's rooftop.

Need to Know

Looking for more travel inspo? Check out my guide The Best of Puerto Vallarta, Mexico.

Advisor - Lindsay Rawitscher

Travel Advisor

Lindsay Rawitscher

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