A Weekend in Healdsburg, CA: The Perfect Day on Repeat

October 15, 2018

If you could live one day over and over again (a la Bill Murray in Groundhog Day), what would it be?
For us, it goes like this:

  1. Wake up, usually pretty early for the sunrise (or before).
  2. Have a spectacular breakfast, ideally outside on a patio or rooftop.
  3. Take a walk while breakfast digests.
  4. Hop on our road bikes around 9:00 or 10:00.
  5. Ride through beautiful country roads (water, rolling hills and/or vineyards preferred).
  6. Find a lunch spot with a great selection of wine.
  7. Ride back to the hotel early-to-mid-afternoon.
  8. Shower.
  9. Nap.
  10. Happy hour.
  11. Sunset.
  12. Progressive dinner at 2-3 quality, casual, chef-driven places.
  13. After-dinner Amaro.
  14. Bedtime.

Where does such a day exist? Several places, actually: in Paso Robles at Hotel Cheval, in Carmel at L’Auberge, in Montecito at San Ysidro Ranch (currently under reconstruction after fires and floods), in the Gargas region of Provence at La Coquillade, in Yountville at Bardessono.
And Healdsburg.
We love Healdsburg. It’s California wine country at its finest (with perfect hot days and cool nights), but it still has a hint of a working-farm-town quality (the farms just happen to be wineries, preferable to us), and the side roads are more about pickup trucks and farm vehicles than wine-country tour buses and Maseratis, at least on weekdays.

First order of business: the perfect hotel. Single Thread Farms comes pretty close. Five rooms, thoughtful attention to detail, and spot-on service.
Side note: We always pay special attention to the in-room gear and tableware as a learning tool, so we can use the ideas appropriately. In this case, the sheets are RH (and they’ve gotten almost as good as Frette or Sferra), bath products are Aesop (extra points), and the towels and bath rugs are supremely fluffy, by Matouk and Frontgate, respectively. The rooms themselves boasted ultra-delicate, high-end Zalto wine glasses. Tableware was comprised of ceramics from Japan, and cutlery was the beautiful and delicate Cutipol we fell in love with in Portugal.
Stocked beverages and snacks are ready upon arrival—always a great idea in making a hotel stay into a true experience.
Since we were on the West Coast, we woke up silly early, but the in-room pour-over coffee system was ready to go. Breakfast was at 7:00, and it was nothing short of spectacular. About 10 small courses, all served at once. And a still-warm seasonal fruit scone with yuzu butter that hit legendary status.
Healdsburg is a great small town for walking through the neighborhoods and around the square, as the locals are getting up and walking to get coffee, trotting alongside their dogs with big smiles. If you lived in a place like this, you’d always be happy, too—especially if you bought your house long enough ago that it wasn’t yet stupid-expensive. If you walk through the neighborhoods, it’s fun to take in the scenes of people who actually live here: Neighbors are having coffee with each other on their front porches and kids are playing in the street. If it’s Saturday, we always hit the farmer’s market, where local fruits, veggies, cheeses, and meats are in abundance.
About 9:30, we got our biking gear on and walked downstairs, where our bikes and water bottles were ready to go in the lobby. Our first-day riding was out West Dry Creek Road, a quiet road filled with vines just starting to turn to fall colors. If you think it’s pretty from your seat in a car, it’s spectacular from the seat of a bicycle. You are missing the whole point of wine country if you’re driving in a car. (Seriously. Get some good bike shorts and get your ass on a bike already.)
We rode out to the junction of Dry Creek and opted to climb up to the dam and Lake Sonoma overlook to work off breakfast—and start earning lunch.

After our climb, we headed to Diavola in Geyserville for pizza and local wine. (Geyserville Gun Club is another great, more bar-like option.)
If you’re so inclined, you can even stop at a few of the abundant tasting rooms. Or you can walk around the town square and find many tasting rooms located here as well.
We stopped to check our emails (it was a workday) and blissfully found virtually no signal. That doesn’t even happen in Bhutan, but for some reason, Verizon is not welcome in this part of wine country.
After a carafe of wine and pizza for lunch, we rode the seven short miles back to the hotel. Shower, nap. Happy hour at 5:30 on the rooftop, with hummingbirds flitting in and out of abundant herb and flower gardens. (Brilliantly, Single Thread’s rooftop is stocked with both sunglasses for the bright sun and blankets for the evening chill.)
We watched the sunset, then headed to a progressive dinner (The Brass Rabbit, Barndiva Gallery Bar, and Amaro at Valette). Back to the rooftop for glimpse of the stars before sleeping in the blissfully comfortable bed.
In summary: 83 degrees, not a cloud in the sky. About 40 miles of riding, great food and wine. Perfect day.
Wake up and repeat, cuing a vacation montage to the tune of “I Got You Babe,” the song Bill Murray kept waking up to in Groundhog Day.
Healdsburg is the perfect weekend getaway, only about 75 miles from SFO (drive midday and don’t mess with rush hour). The town square still has a few cute shops, and many great restaurants.

Our favorites:

  • Shed for breakfast or lunch (if your hotel doesn’t have Single Thread’s breakfast). It’s retail meets food in one of the best examples.
  • Campo Fina. The best back patio, pizza, and meatballs.
  • The bar at Barndiva (or the even more casual Gallery Bar).
  • The porch at Madrona Manor (just outside of town) for a burger and drink.
  • Valette (also prefer the bar).
  • Duke’s (either the bar, or the next-door place with small bites).
  • The food at Chalkboard is pretty good, but the lights are too bright and the bar feels a little too connected to the adjacent hotel.
  • Oakville Grocery for lunch on the patio or to stock up on picnic-type snacks.

We also splurged for a dinner at Single Thread Farms during our visit. The multi-course, fine-dining meal isn’t really our speed, but even with eleven courses, this one didn’t feel like death by food. It was an extraordinary experience. Once.

To stay:

Hotel Healdsburg is a close second (and less costly) option to the hard-to-get-into Single Thread. H2 Hotel and the very private Duchamp are also great choices.

Favorite wineries:

  • Armida (location on the hill)
  • J (sparkling wine)
  • Copain (also a great property high on the hill; by appointment only)
  • Truett Hurst (live music on weekends)
  • Alexander Valley (one of our favorite everyday wines)
  • Iron Horse (also sparkling wine and a little further drive, but the hilltop location is worth it)

Want to Engage Shea for your upcoming project?

Get In Touch