San Francisco to Healdsburg and the Anderson Valley

Fuel up for the ride north with a Thai iced coffee and a croissant sandwich studded with egg and bacon. The owner sources all of her beans (arabica) from Northern Thailand and roasts them onsite. A menu of traditional Thai dishes includes khao soi and aroi mak mak, all packaged to go. Or try the hibiscus boba for a tongue-twisting treat.
Open 6:30 am - 4 pm, Monday to Friday, 7:30 am - 4 pm Saturday, closed Sunday.

Located on the southwest corner of Healdsburg Plaza, this is your go-to spot for picnic provisions needed at any point along your journey. The team here has been curating picnics for decades, so call ahead and they can put together the perfect assortment for your outdoor eating desires. Or just step up to the counter and order. You can't go wrong with a Wagon Wheel sandwich. Named for the Cowgirl Creamery cheese which forms its base, it's layered with Fra'mani rosemary ham and Dijon. Yum.

A hub of activity, Healdsburg is Sonoma's northern hub and its downtown plaza is one of the prettiest around with a wide green lawn and a gazebo. Bring a bottle of wine and the Wagon Wheel sandwich you just bought at Oakville Grocery and grab a seat on the grass and watch the world go by for a while. When sated, meander around the plaza, poking into the shops that ring the square.

Just north of Healdsburg, Jordan Winery is 1,200 acres of vineyards and open space. A Vineyard Tour and Tasting involves a short walk to a supreme vantage point where you can see the valley nearly in its entirety. Your guide pours four wines to be paired with Sonoma cheeses and artisanal salumi from Journeyman Meat Co. It's a great spot to have lunch. You won't want to leave.
Advance reservations are strongly recommended on the official website.

Though most of the wineries in the area will be closed by the time you start driving along the Wine Road, it is a lovely drive anyway, one of the most scenic routes in this part of California. Wind your way along the road and, if luck is in your corner, there will be a winery open for tastings in the late afternoon. Savor your good fortune!

Spend a few minutes walking around the quaint Anderson Valley town of Boonville. The community was once so remote from other towns that a unique dialect cropped up. Locals cherish their "outsider" status, as even most other Californians don't even known about this spot. You, however, are here for dinner from chef Perry Hoffman. The chef—who earned a Michelin star at étoile at Domaine Chandon in Sonoma, and went onto helm the kitchen at Healdsburg's SHED (where Little Saint now holds sway)—returned to his roots in the area and is cheffing at the Boonville Hotel. Chef calls the restaurant a roadhouse and in the current atmosphere of "anything goes" with restaurants, why not? Chef changes the prix fixe menu every week, so expect a seasonal and local focus when you arrive. Recent dishes have included halibut with green garlic broth and fiddlehead ferns and grilled lamb chops with Moroccan spiced kumquats, Swiss chard, and lovage.
Reservations for dinner can be made via Tock

Boonville is in the bucolic Anderson Valley where hotels are few and far between. Advanced booking is recommended whenever possible. At Boonville Hotel and Restaurant, there are just 17 rooms, some in the main building and the others unique cottages or other one-of-a-kind spaces around the hotel property. Some have private courtyards or patios.
Reservations for the Hotel can be made on their website in advance. Book Now