FIVE MILES: Sausalito + Cavallo Point
Stellar sushi, holistic makeovers, and a Michelin-starred restaurant in the village across the bay.

9 am Cross the Golden Gate and overshoot Sausalito by a few miles for breakfast at the Dipsea Café, just off the Stinson Beach/Mill Valley exit from 101 North. Marinites worship at this brekkie altar because of the nonstandard offerings, like a homemade gravlax platter, cheese blintzes, and a sinful chorizo-tortilla scramble. 200 Shoreline Highway, Mill Valley, 415-381-0298.

10 am Head over to Sea Trek in Sausalito for some bay kayaking. Your options are many: Take a guided paddle under the Golden Gate Bridge, or stay closer to shore in the Sausalito harbor. You can also rent a beginner’s sit-atop kayak and take it out on your own, skipping the intro class. Schoonaker Point Marina, Sausalito, 415-332-8494.

1 pm Dry off and head to town for a well-earned lunch at Sushi Ran. There’s a simple reason city dwellers cross the bridge for a fix at this sushi institution: the fish. Shark-skin flounder flown in from Tokyo’s Tsukiji market sits alongside a spicy tuna roll that even purists salivate over, and you can’t go wrong with the omakase lunch special. Reservations are recommended for the main dining room. 107 Caledonia St., 415-332-3620.

2 pm Spend a long afternoon at Cavallo Point, the otherworldy, sprawling lodge nestled within Fort Baker. The simple but luxurious design blends into the national park setting, making the 3-year-old resort somewhat of a hidden gem. The Healing Arts Center & Spa offers more than just the usual facials and massages. There’s also acupuncture, herbal consultations, and nutritional counseling. Better yet, get an internal makeover with Cavallo’s resident doctor, Brad Jacobs, who runs Cavallo’s Integrative Medicine program. Sit down with him for an hour or two, and Dr. Jacobs will design a personalized health regimen, including diet, exercise, supplements, and mind-body relaxation techniques. Afterward, relax by the roaring fire, and order from the tea bar. 601 Murray Circle, Sausalito, 415-339-4700.

6 pm Though the vibe at Cavallo’s bar, Farley’s, is laid-back, there’s an air of old money, and they make a mean negroni that goes nicely with it. Afterward, settle in for dinner at Murray Circle, where executive chef and Michael Mina alum Joseph Humphrey has earned himself a Michelin star for his imaginative yet restrained take on fresh and local. You’ll find Devil’s Gulch rabbit (with prosciutto, celery root, chanterelles, smoked dates, and braised romaine), Liberty Farms duck (with roasted foie gras and turnips cooked in caramel, fennel, and licorice), and Drakes Bay oysters from Inverness served three ways. Save room for the wine-paired chocolate tasting at the end.

10 MILES: Lake Merritt + Piedmont
Pastries, rowboats, and a hidden hot springs in Oakland’s urban enclave.

9 am Take the Bay Bridge to 580 East to Lake Merritt, Oakland’s 3.4-mile-round lagoon just outside downtown. To the north of the lake, stop at Berkeley’s Cheeseboard offshoot, Arizmendi Bakery, for coffee, sticky pecan rolls, corn-cherry scones, or a sweet brioche knot. 3265 Lakeshore Ave., Oakland, 510-268-8849.

10:30 am Drive 5 minutes to the Lake Merritt Boating Center to rent a rowboat. The boats are classic (and make for a romantic floating picnic), but if you want something easier to steer, the center also rents out pedal boats and kayaks. Make stops along the beaches and parks on the shore where fishermen are casting, or head straight

out to the center of the lake, bring your oars into the boat, and then relax in the sun as you drift back. 568 Bellevue Ave., Oakland, 510-238-2196.

1 pm After you drop off the boat, drive clockwise around the lake to the other side. Opposite the boating center is Lake Chalet, owned by Gar and Lara Truppelli of Beach Chalet and Park Chalet in Golden Gate Park. For a satisfying lunch with a view, grab a table or couch at the end of the dock, and order sweet potato fries or calamari with a pint of one of the house-made ales, such as a crisp Lady of the Lake pale with a hint of hops. You deserve it. 1520 Lakeside Drive, Oakland, 510-208-5253.

2:30 pm Spend the rest of the afternoon on quaint Piedmont Avenue, just two miles north of the lake. Between Pleasant Valley Avenue and West MacArthur Boulevard, you’ll find a row of restaurants, coffee shops, bookstores, and boutiques, plus the Piedmont Landmark Theatre, a tiny three-screener that shows (mostly) quirky independent films and cult classics. Hidden behind a glass storefront on the same stretch of sidewalk is Piedmont Springs. The spa is great for soothing aching muscles with a massage, quick steam, or time in one of the private “combination” rooms with an outdoor hot tub and cedar-lined sauna room, for just $22 an hour. 3939 Piedmont Ave., Oakland, 510-652-9191; 
4186 Piedmont Ave., Oakland, 

7 pm For the past two years, Oakland’s been buzzing over chef James Syhabout’s Commis. The white, open-kitchen dining room is minimalist and anything but pretentious. The four-course menu ($68), based on California seasonal cuisine, keeps it simple with just nine dishes including desserts. Think rich sunchoke soup; roasted chicken with braised garlic, potato, and caramelized onions; and a creamy panna cotta punched up with citrus, pomegranate, and coriander. 3859 Piedmont Ave., 510-653-3902.

30 MILES: Woodside + Half Moon Bay
Power breakfasts, towering redwoods, and big red wines half an hour south of town.

10 am Drive down Interstate 280 to Woodside for breakfast at Buck’s, which looks like a kitsch-splattered diner owned by a crazy man (that would be Jamis MacNiven, father to the local MacNiven brothers who run Woodhouse Fish Co.), but it’s actually a gathering spot for Silicon Valley power brokers. You’re here for the legend more than the food—though French toast made with croissants is definitely worth a try. 3062 Woodside Road, Woodside, 650-851-8010.

11:30 am Head inland on Skyline Drive to Purisima Creek Redwoods Open Space Preserve, a little-known piece of nature in the Santa Cruz Mountains. Its 21 miles of groomed hiking trails take you through redwood groves, canyons, and hilltops with sweeping views of the coast. Skyline Boulevard, 650-691-1200.

3 pm Continue north on Skyline Boulevard toward Half Moon Bay. Just a few miles before its downtown, stop at La Nebbia Winery. Don’t let its down-home tasting room fool you. The winery produces well-regarded Sangiovese, Cabernet, and Muscat. Tastings are only $8, there are light snacks on hand (or you can bring your own), and you’re encouraged to wander out to the bocce court for a leisurely game. On the second and fourth Sunday of the month, the winery hosts local musicians. 12341 San Mateo Road, Half Moon Bay, 650-726-7074.

5 pm Just north of HMB on Highway 1, Sam’s Chowder House is the definitive place to be come dinnertime. Have drinks on the deck’s Adirondack chairs overlooking the ocean, and warm up by the heat lamps and fire pits. On Saturdays 4–8 pm and Sundays 1–5 pm, there’s live music outside, everything from rock to jazz, blues, reggae, and more. Afterward, go inside for crab cakes, cioppino, clams with linguini, or a decadent Maine lobster roll. True to its East Coast roots, Sam’s serves both both New England and Manhattan-style clam chowder. There’s homemade soft-serve or a root beer float for dessert. With home a mere half hour away, you can stay as long as you like. 4210 N. Cabrillo Hwy., Half Moon Bay, 650-712-0245.

By 7×7 Editors

This is our weekly guest post from our friends at 7×7, a site that keeps you up on the best of SF. We’ve teamed up for an exciting partnership to bring you a fantastic Date Night idea each week. Be sure to check out their blog for hourly doses of the best of SF.