Fly into Santa Rosa’s Charles M. Schulz–Sonoma County Airport (Alaska has a direct flight under two hours) on a hump day in time for downtown to be taken over by the Wednesday Night Market (summer only), and then head to Stark’s for steak, Jackson’s Bar and Oven for delicious wood-fired pizza, or El Coqui for Puerto Rican cuisine. Be reminded Portland isn’t the only “rose” city with a visit to Luther Burbank Home and Gardens, where Burbank’s horticultural advances (and roses!) still astound 100 years later. (Burbank is also the namesake of Santa Rosa’s Rose Parade & Festival, in May.) Be close to it all at the historic Hotel La Rose in Railroad Square (hotellarose.com, rooms from $139).

For a Sonoma County tour, head west in a rental car on a route used by the Amgen Tour of California bicycle race (on hiatus in 2020, so don’t worry about running into it) and stop by Korbel Champagne Cellars. The bubbly maker might be best known for its $13 Brut, but the deli features some much nicer vintages to enjoy on the patio with salads and sandwiches.

Guerneville, a picturesque town submerged by major floods last February, is about three blocks long and best enjoyed on foot. Wander through art galleries and walk across its narrow, century-old bridge over the Russian River (which cars drove over into the ’90s, though now it’s pedestrian only). Eat at Boon Eat & Drink for incredible seasonal menus, or enjoy classic diner fare at Pat's, on Main Street since 1940. A walk through Armstrong Redwoods State Reserve, two miles north of Guerneville and home to an ancient stand of coast redwoods, is a must.

Depending on when you get to Occidental, hit the train-themed, cash-only Howard Station Café for its infamously hearty breakfast or a grass-fed-beef burger and classic shake (the diner also has a quinoa-heavy “healthy alternatives” section—it’s on the Bohemian Highway, after all), or grab dinner at Hazel for wood-fired fine dining paired with local wines. (Aim for the weekly Thursday free corkage night on wines from the county.) Stop at Hand Goods for local gifts, pottery to hand-knit sweaters.

Keep on the cyclists’ route out to the coast on Coleman Valley Road, and head south toward Bodega, where Bodega Head offers a beautiful trail around the peninsula, rife with whale-viewing opportunities and the sound of foghorns. Stop at Fishetarian for the best calamari you’ve ever had. Goat Rock is a star of many car commercials, but the best (and far less-crowded) beaches for combing on this stretch of Highway 1 are Portuguese and Schoolhouse.

Here you have a choice: Continue south on the 1 and make your way into Petaluma, home to incredible used bookstore Copperfield’s, a riverwalk designed around local coffee and fine bistros, and historical buildings that make you feel like you’re in the Old West. Or turn back toward Santa Rosa, stopping in tiny Freestone at Wild Flour for all you’ve ever dreamed bread could be. Get the fougasse loaf, then get another, and thank me later. Across the street is Osmosis Day Spa, if you’re in the mood for a massage or a cedar bath. You’ll drive through Sebastopol, where it’s easy to stop for just an ice cream cone at Mimi’s or to spend an entire day. The town’s Barlow district, which also flooded last February, is packed with wine tasting rooms, coffee shops, and restaurants.

Just want to drink? For an alternate itinerary, pick a designated driver and get ready for all wine, all the time. You can literally eat and drink all day around Sonoma Plaza, Napa’s Oxbow Public Market, or, farther north, Healdsburg’s tasting-room-packed central downtown. No winery around here will disappoint. Favorites include Bella, Harvest Moon, Iron Horse, Dutton-Goldfield, and Kunde in Sonoma County, and Chateau Montelena, August Briggs, Storybook Mountain, and Schramsberg in Napa. (Beer-wise, there are big names like Russian River in Santa Rosa, with a new outpost in Windsor, and Petaluma-based Lagunitas—but smaller breweries like Seismic, Moonlight, and HenHouse also shine.)

For a luxe all-wine weekend, consider making your home base in Calistoga, a half-hour northeast of Santa Rosa. Five-room Embrace Calistoga might be the friendliest B&B you’ve never wanted to leave (embracecalistoga.com, rooms from $269), while just up the road Indian Springs boasts 17 acres with a lodge, spa, cottages, houses, and four thermal geysers feeding an Olympic-sized mineral pool (indianspringscalistoga.com, rooms from $249). Napa County is studded with Michelin stars; in Calistoga, try Veraison for seasonal fare with an extensive wine list (and candy cap beignets!). Afterward, go to Susie’s bar to drink with the locals and get tips for how to spend your last day before flying home.