Your roadmap to one epic Bay Area weekend
When it comes to fun, the Bay Area has everything—surfing, mountain biking, wine tasting, hiking … the list goes on. But when the weekend rolls around, this wealth of possibilities can lead to a decision-making crisis. With so many options, how do you choose?
Our solution: don’t limit yourself. Do them all. We’ve planned an itinerary packed with adventures that will let you sample the Bay Area’s riches all in one seriously epic weekend.
Start the weekend off right by flying in a plane over the bay. Head to Oakland International Airport and get up high in a Cessna 207. You'll get gorgeous aerial views of San Francisco, Oakland, Alcatraz, and the Golden Gate Bridge.
Next up, take a 30-minute drive to Half Moon Bay Brewing Company for lunch on the patio. Snag a seat by the water and order a dungeness crab roll or baja tacos along with a pint of one of their award-winning beers. Half Moon Bay Kayak Company
After lunch, head to Half Moon Bay for stand-up paddleboarding. An instructor will show you the basics before sending you off to explore Pillar Point Harbor or the open ocean. If paddleboarding isn’t your thing, rent a kayak instead. Either way, you’re bound to see some seals and sea lions.
Next, take a leisurely drive up Highway 1 to Point Reyes Station and check in at the Black Heron Inn, which sits on the edge of 70,000 acres of protected seashore. Explore the natural beauty around you or take a five-minute drive into town to sample cheese at Cowgirl Creamery. For dinner, there’s Italian food made with local ingredients at Osteria Stellina. The menu ranges from oysters to gourmet pizza to Rossotti Ranch braised goat with herbed polenta.
Getting up with the sunrise is worth it for a half-day safari by Point Reyes Gone Wild. Local guide Daniel Dietrich will lead you on the five-hour trek through Point Reyes National Seashore, looking for bobcats, coyotes, elk, otters, or any other animal that decides to show itself that day.
“It’s totally customized for whatever experience people want,” he says. “I had a gentleman from Southern California who said, ‘I don’t care about anything except seeing a bobcat.’ So that’s all we did all day, look for bobcats. We saw three bobcats that day.”
After working up an appetite wandering through the wilderness, treat yourself to a three-hour food tour with Savor Healdsburg. Stops include tapas at Bravas, artisan bread at Costeaux French Bakery & Cafe, and sips of small-lot vino at Stark Wine Company.
Afterwards, explore downtown Healdsburg and its many Sonoma County wine-tasting opportunities. There’s also Copperfield’s Books if your stomach needs a rest. Later on, have dinner at Barn Diva—the “frisèe lardon” crispy pork belly is excellent. Then check into Hotel Healdsburg for the night. The design is sleek and modern, but the atmosphere is relaxed.
The next morning at 6:30 or 7 a.m., grab a coffee at Flying Goat and some sandwiches to go at Oakville Grocery. Hop in the car and drive down to Hallcrest Vineyards in Felton, near Santa Cruz, for a beekeeping demo with Honey & Wine Tastings.
For two hours, you’ll learn about beekeeping, see a live frame of bees, and taste honey made from black sage, wildflowers, star thistle, and other pollinating plants. Each plant’s pollen produces a different flavored honey. Finish up with wine tasting in the vineyard.
Once your glass is empty, hoof it to nearby Gramhill Store for your next activity: Horseback riding in the Santa Cruz Mountains. For an entire afternoon, you’ll ride through redwood forests filled with old growth trees that are thousands of years old and 300 feet tall.
Don’t worry if you’ve never ridden a horse before. “You just have to have a little heart and a little bit of courage,” says tour guide Steve Roth.
Heart and courage. One thing’s for sure: you’ll definitely use both of those on this action-packed weekend. Wind down with a drive over to Santa Cruz for pizza at La Posta followed by watching the sun set over the ocean—and your adventure—at Lighthouse Point Park.