San Francisco Bay Loop

With towers soaring 746 feet/227 meters into the sky, its span arcing across the mouth of San Francisco Bay, and all of it painted fire-engine red, the iconic Golden Gate Bridge makes a dramatic destination.

Yes, you can simply drive across the bridge, but it’s more fun to walk (even for just a portion of the spa). It can get a bit cold and windy, especially when the fog slips in (common in summer), so dress in layers. Biking across the bridge is another fun option—rental companies abound (two favorites are Blazing Saddles and San Francisco Bicycle Rentals); most bikes come with route maps detailing where to ride from San Francisco across the bridge to towns like Sausalito and Tiburon, in neighboring Marin County. Back in the city, there’s a nice gift shop and a café, and paths let you wind down to historic Fort Point, completed in 1861 as a military outpost.

Follow the coast, past broad Stinson Beach and the sparkling Bolinas Lagoon (a great place for kayaking and birding) to this extraordinary peninsula. Jutting dozens of miles out into the sea, Point Reyes is loaded with amazing discoveries, including remarkable wildlife, deep forests, dramatic sea cliffs, and remote beaches.

No matter what time of year you visit, there’s something extraordinary to see and do. In winter, travel to the tip of the point (a shuttle takes you the last few miles) to look for migrating gray whales passing remarkably close. (It helps when you just out into their swimming lanes). In spring, walk the trail to Chimney Rock to see countless wildflowers (look for puffins nesting on oceanfront cliffs), or follow a trail lined with irises into a rare Bishop pine forest. In summer, watch the cool fog tumble in, then have a cup of cocoa in the cozy village of Point Reyes Station. And in fall, listen for the eerie bugle of tule elk bulls; can usually spot individuals or small herds of these native elk in the Tomales Point preserve area, at the tip of the park.

To get yourself oriented, stop by the outstanding Bear Valley Nature Center, with kid-friendly displays, maps, and helpful rangers. The fairly flat, stroller-friendly Bear Valley Trail makes a popular leg-stretch or bike ride.

Your road trip now heads inland to explore some of the finest wine country in the world.

This quaint fishing village has an interesting past and a vibrant present. Alfred Hitchcock shot his 1963 classic The Birds here and in nearby Bodega, and tourists flock to the area to see familiar locations from the film, including blufftop Bodega Head, which offers sweeping views of the Pacific Ocean. Bodega Bay is big on birds in general, offering three separate ways to spot our feathered friends, including the Bird Walk Coastal Access Trail. Looking to the skies is a bit of theme here: Bodega Bay boasts two kite shops, Second Wind and Candy & Kites—how many towns with a population of around 1,000 can say that? Pro tip: Be sure to take advantage of the ultra-fresh seafood options in Bodega Bay, and if you see an open table at the Spud Point Crab Company, grab it.

Much of Sonoma County has a small-town feel to it—the many independently run wineries, restaurants,and boutiques contribute to that—but it’s actually a huge place. Bordered by San Pablo Bay in the south, the Mayacamas Mountains in the east, and the Pacific Ocean to the west, Sonoma Cover covers 1,768 square miles, a significant portion of that comprising farm land and vineyards. The wine scene is truly exceptional: More than 425 wineries operate here, offering breathtaking diversity in terms of varietals, styles, price points, and terroir. You probably won’t be able to experience all 18 American Viticultural Areas here, so start with a few. Consider exploring the Carneros region, a charming appellation straddling the Napa and Sonoma Valleys and producer of some of the region’s best Chardonnay, Pinot Noir, and sparkling wines. (Bubbly fans should pay a visit to Gloria Ferrer—for the Blanc de Blancs and the epic views.)

A haven for backyard artists and coffee-shop philosophers, Berkeley has deep roots in the Flower Power movement of the 1960s and ’70s. But while California’s spirited city of free speech still stands strong, Berkeley can also boast of a booming food, wine, and craft-brew scene—this is, after all, the home of the legendary Chez Panisse—sprinkled throughout with arts and culture. Add an easy-to-use public transit that makes San Francisco a quick light-rail ride away, and Berkeley rates high on any Bay Area must-see list. Top-notch University of California, Berkeley, gives the city an energetic jolt, and students from around the world add an international and intellectual flair. How diverse is Berkeley? Along the main drag of University Avenue, you can buy an exotic outfit at Sari Palace, sample Indonesian food at Jayakarta, and enjoy house-roasted beans at Algorithm Coffee Co.Stop by the visitor information center a block north of the downtown Berkeley BART station (the hub for the local light-rail system that accesses San Francisco and other Bay Area towns).

Diverse, dynamic, artsy, edgy—Oakland has seen an influx of young locals, drawn by the vibe, move into downtown lofts and condos. With them came the single-pour coffee bars, cafes, galleries, and clubs. Lower costs in the East Bay have also lured chefs—both established big names and new-gen kitchen whiz kids—to open restaurants here, in settings ranging from splashy Art Deco (Flora) to sleek hipster chic (Plum).

Jack London Square, an inviting complex perched on the edge of San Francisco Bay, mixes outdoor fun with indoor diversions. The square is named after the intrepid adventurer and author of Call of the Wildand The Sea Wolf, a book allegedly inspired by tales told by folk who frequented the legendary—and still open—Heinhold’s First and Last Chance Saloon. Near the sloped entrance to the historic watering hole, the wall hands on the wall clock haven’t budged since April 18, 1906—the moment a massive quake struck the Bay Area, and jolted the building so much the timepiece stopped ticking. Settle in and talk to your elbow-mate at the bar; you never know what tall tales you might here.

But save your visit to this historic bar until later in the day. When the sun’s up and shining, paddle a kayak around the adjacent Oakland Estuary, especially lively during the fall bird migration. Post paddle, stroll the square to visit shops, or tour two historic vessels: the Lightship Relief, a floating lighthouse which aided navigation along various U.S. coastlines from 1951 to 1974, and the USS Potomac, President Franklin Delano Roosevelt’s historic yacht (ask about bay cruises). Dine at inviting options like Baia for organic pasta, or have crab cake benedict for brunch at Oakland Grill. Farmers’ markets and outdoor movies add to Jack London Square’s neighborhood-y appeal.

Famous for grand-dame Victorians, classic cable cars, dynamic diversity, trend-defining, Michelin-starred cuisine, a beautiful waterfront, and a soaring crimson bridge, San Francisco, aka the “City by the Bay”, truly has it all and stands out as an ultimate must-see.

Pedal bikes across the Golden Gate Bridge and back, then explore the lush Presidio, a former military base that’s now a park, or head into Golden Gate Park to visit museums and row across a secret gem, Stow Lake. Continue along the flat Embarcadero to the bustling Ferry Building Marketplace, the Exploratorium science and learning museum, and colorful Fisherman’s Wharf.

Take a cable car ride to the high-end shops in bustling Union Square, with a stop for Italian pastries and cappuccino at Emporio Rulli right in the square. At night, catch a show in the theater district. For more nightlife and dining, stroll Valencia Street in the Mission, a trendy and eclectic hotbed of restaurants and bars, and awesome late-night scoops at Bi-Rite Ice Cream.