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Often referred to as America’s most European city, regularly topping travel magazine favorite cities lists, and famed for its postcard-perfect vistas, San Francisco is indeed, as John Steinbeck described, “a golden handcuff with the key thrown away.” But it’s more than topography that makes the City by the Bay one of the top places for 25.5-million-plus visitors to leave their hearts each year. Molded politically, socially, and physically by its history, and refined by a variety of natural and manmade events, the city’s character is like no other.

San Francisco Today

During the past 2 decades, California’s fourth-largest city has weathered the wild ride of two boom-or-bust economies. The first, in the late 1990s, was the famed “Dot-com boom,” which, when it went bust in the early 2000s, left the city’s residents, businesses, and real estate market reeling from economic whiplash. The second, which is underway now, has seen even more growth and influx of new wealth, and it seems there’s no end in sight. The Bay Area is the epicenter of the now-established Internet industry, and San Francisco has become the most compelling crash pad for young entrepreneurs and tech workers (who have access to big luxurious private buses that shuttle them to Silicon Valley). All this has made the face of the city change at wireless Internet speed. 

Already the state’s most densely populated city, with 864,000 residents (it’s also the second most densely populated in the nation, behind New York), San Francisco has been strained even further by a nearly 10% population increase in the last 7 years—while ethnic diversity has diminished. Teardown homes in nice neighborhoods are selling for upward of $2 million. Room rentals in shared homes regularly go for more than $1,200. Once-desolate industrial areas are now being developed into multi-use communities teeming with glistening new luxury condos, chic restaurants, and trendy businesses. 

In updating this guide, I repeatedly ran up against shocking evidence of just how ritzy our city has become. You can see it most clearly in the restaurant scene, which mirrors the great divide our city and nation is experiencing: While there are lots of expensive new restaurants opening, where entrees cost $30 or more, and there are plenty of supercheap grab-and-go places to eat, there are fewer and fewer “middle class” restaurants—which used to be one of our most abundant attributes—and those that survive seem very much like relics from another time.

Not surprisingly, there’s backlash. Reports show that middle-income residents are moving out of San Francisco at rates much faster than others are moving in. Not only is this a problem for restaurants, hotels, and other businesses, who struggle to find and keep lower-pay-grade workers, it has also meant fewer of the colorful, offbeat residents that used to be a significant part of the city’s bohemian culture. In the fall of 2011, the Occupy SF movement—itself part of Occupy Wall Street—brought the city’s economic struggles front and center, as hundreds camped out and protested in San Francisco, Oakland, and throughout the Bay Area. (A legitimate question heard from the encampment in Justin Herman Plaza: Why can’t everyone who works in San Francisco afford housing in or near San Francisco?) 

And, of course, there are still the typical big-city problems: While crime is generally down over the past couple of years, drug abuse is up, and despite efforts to curb the ubiquitous problem of homelessness and panhandling, it’s still a thorny—and shockingly visible—issue.

Still, you can’t help but feel San Francisco is the place to be right now. Its convention halls are fully booked, hotels and restaurants are opening around every corner, and San Franciscans eagerly line up for hot clubs and nightspots, theaters and film festivals. It’s hard to predict just how much the continued flood of privileged new residents will affect its tolerant, alternative soul, but so far, San Francisco continues to embrace diverse lifestyles and liberal thinking. While it may never relive its glory days as King of the West Coast, San Francisco will undoubtedly retain the title of Everyone’s Favorite California City.

California’s New Cannabis Laws

In November 2016, California voters passed Proposition 64, legalizing the sale and possession of recreational marijuana (for persons age 21 or older) after January 1, 2018. But before you jump on a plane and head to the Golden State looking for a quick legal high, know that each locality still has to decide on how much local tax to impose and how to license cannabis retailers and distributors, not to mention regulating cannabis growers. You won’t find the streets of San Francisco lined with pot boutiques for a while. Until then, the only marijuana that can be legally sold is medical marijuana, to holders of a medical marijuana card. Which, in practice, is not that hard to obtain, but still. . . . 

A Brief History of Wine Country

Like most everything else around San Francisco, the Northern California wine industry began with the 1849 Gold Rush. It took a bunch of European immigrants—most of whom originally came seeking gold—to discover that the hilly countryside north of San Francisco offered a perfect climate for viticulture. Hungarian nobleman Agoston Haraszthy imported some 300 different vines from Europe for his Buena Vista winery, founded near the town of Sonoma in 1857; the next year, 1858, Bavarian winemaker Jacob Gundlach opened another winery nearby which is still in business today. Meanwhile, in Napa Valley to the east, Englishman John Patchett began planting vines in 1854, opening a winery in 1858; Prussian immigrant Charles Krug, who’d worked for both Patchett and Haraszthy, founded his own winery in St. Helena in 1861. (Today it’s owned by the Mondavi family.) Fellow Germans quickly followed—Jacob Schramsberg with his winery in 1862, and former Krug cellarmaster Jacob Benziger in 1876—along with Finnish-born Captain Gustave Niebaum, who began making Bordeaux-style wines at his Inglenook Winery in 1879 (now part of Francis Ford Coppola’s wine empire). In 1862, Gold Rush millionaire Samuel Brannan launched Napa Valley tourism by building a spa town around the natural hot springs of Calistoga. 

Through the 1870s and 1880s, the American wine industry burgeoned, surviving an invasion of the native phylloxera bug (accidentally introduced to Europe in the 1860s, where it nearly wiped out the continent’s vineyards—giving American wines an edge in the market for a couple of decades). In 1889, when Inglenook wines won gold medals at the Paris World’s Fair, the American wine industry really became a world player. 

All of this came crashing to a halt in 1920 when Prohibition made alcoholic beverages illegal. Production fell by a whopping 94%, with only a few winemakers hanging on by making communion wines, which were exempt. By the time Prohibition was repealed in 1933, the California wine industry had collapsed. For various social and cultural reasons, Americans had switched from wine to cocktails and beer. The few wineries that survived flooded the market with cheap, low-quality wines.

A new wave of California winemakers in the early 1960s, however, began to focus on quality. Led by Robert Mondavi, who opened his Oakville winery in 1965, these vintners began marketing their wines with varietal names (Pinot Noir, Chardonnay, Chablis) instead of the place names of European wines (such as Burgundy or Bordeaux). As gourmet chefs like Julia Child and James Beard promoted fine dining in the later 1960s, Americans aspired to drink wine again—but not domestic wines, which still were considered inferior. All that changed in 1976, when a highly publicized blind taste testing in Paris—presided over by French wine experts—stunned the world by awarding top honors to two California wines, a Chardonnay by Chateau Montelena and a Cabernet Sauvignon by Stag’s Leap Wine Cellars, both from Napa Valley. The stigma of California wines vanished seemingly overnight. Between 1980 and 1989 in Sonoma County, grapes went from being the fourth-largest agricultural product to being its top crop.

And along with the wine boom came something new: enotourism. Napa Valley began to market itself as a tourist destination for wine lovers in 1975. Spurred by their efforts, wineries opened sleek tasting rooms and developed tours of their cellars and wine-making facilities, while luxury resorts opened all around the valley. By the mid-1990s, it had become a culinary destination as well, with Thomas Keller’s famed French Laundry restaurant in Yountville opening in 1994 and a branch of the Culinary Institute of America opening in 1995 in St. Helena. Neighboring Sonoma County, with more small, family-owned wineries, was quick to jump onto the enotourism bandwagon as well, offering a more laidback alternative to Napa. 

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.