Your guides will meet you in San Francisco, and we’ll transfer you north across the Golden Gate Bridge to Marin County. Begin with the essentials: a bike fitting, safety talk, and map review before tasting cheeses at Marin French Cheese company. Our ride will take us past Sonoma’s rural ranches and pastoral farms. The biggest climb of the week comes early, but is rewarded with beautiful views of Tomales Bay. After lunch at a local cyclists’ hangout, we’ll continue to the sleepy town of Freestone, then choose a van transfer or continue a few more miles on the bike to the Bodega Bay Lodge. Tonight, we kick off the tour with an exquisite meal at Terrapin Creek. Accomplished: 34 miles / 55 km, elevation gain: 1,469 feet / 448 meters Longer Option: 43 miles / 69 km, elevation gain: 1,748 feet / 533 meters

Today’s ride highlights the variety of Northern California: start by pedaling past the rugged headlands of the Pacific coast and pause for a photo against a backdrop of rocky cliffs and dramatic, cresting waves. After a coffee stop, we veer east along the Russian River and arrive at a redwood forest. Marvel at these mystical 1,400-year-old trees, then picnic beneath their 300-foot canopy. En route to Healdsburg, we’ll stop on the historic West Side Road to taste crisp Chardonnays and velvety Pinot Noirs at a standout winery. Our favorite Healdsburg restaurant hosts us for dinner this evening. Accomplished: 47 miles / 75 km, elevation gain: 2,066 feet / 630 meters Shorter Option: 38 miles / 61 km, elevation gain: 1,902 feet / 580 meters

This morning, ride West Dry Creek Road in a region replete with welcoming vineyards. As we cross into Alexander Valley, quiet backroads reveal dreamy views of the Mayacamas Mountains, and we’ll stop for a coffee amidst acres of vines. Lunch is served at a favorite outdoor sandwich shop before we return to the hotel for an afternoon by the pool. Tonight is your free night—take advantage of the 30+ tasting rooms lining Healdsburg’s historic square, and turn to your guides for a dinner recommendation to suit your tastes. Accomplished: 38 miles / 61 km, elevation gain: 1,519 feet / 463 meters

Bid Healdsburg farewell this morning as we pass once more through the Russian River Valley. This time, we’ll continue east on Chalk Hill Road, an eight-mile stretch lined with pastures, stables, and celebrated vineyards. Turn towards Napa Valley where the road opens up with views of Mount St. Helena, and finish the ride with an epic lunch. This afternoon, settle into your next hotel—a stunning spa property in Calistoga—with a well-deserved massage, or explore the perfectly manicured town before dinner on your own. Accomplished: 34 miles / 55 km, elevation gain: 1,574 feet / 480 metersLonger Option: 37 miles / 59 km, elevation gain: 2,020 feet / 616 meters

The focus of our day is discovering a side of Napa that remains relatively untapped. Begin by riding the Silverado Trail, a road with a dedicated bike lane running its entire length, then climb out of the valley into a classic Northern California chaparral. After a lovely local lunch, there’s a bit more climbing before we break into a downhill past Lake Hennessy and into St. Helena. Perhaps our favorite surprise of the week is the beer tasting hosted by Nile in his St. Helena brewery, Mad Fritz. With your palate primed in both olive oil and beer, choose to keep riding, transfer back to the hotel, or explore the shops and tasting rooms of St. Helena. This evening’s epic final dinner is an affair to remember at Solbar, the hotel’s Michelin-starred restaurant. Accomplished: 41 miles / 66 km, elevation gain: 2,214 feet / 675 meters Longer Option: 53 miles / 85 km, elevation gain: 2,755 feet / 840 meters

On your final morning, join your guides for an invigorating morning ride or sleep in and linger over one last poolside breakfast. Around mid-morning, your guides will drive you back to San Francisco via Napa Valley for a final, sweeping overview of some of the region’s most famous vineyards. Or, we can help with alternate transportation if you plan to stay a little longer in Napa.