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Union Square -- is the commercial hub of San Francisco. Most major hotels and department stores are crammed into the area surrounding the actual square, which was named for a series of violent pro-union rallies staged here on the eve of the Civil War. A plethora of upscale boutiques, mediocre restaurants (soon to be improving), and galleries occupy the spaces tucked between the larger buildings. A few blocks west is the Tenderloin neighborhood, a patch of poverty and blight brimming with drug addicts and homeless people. While most keep to themselves, this is definitely a place to keep your wits about you. The Theater District, also populated by down-on-their-luck residents, is 3 blocks west of Union Square.

The Financial District -- East of Union Square, this area sometimes referred to as Fi-Di—bordered by the Embarcadero and by Market, Third, Kearny, and Washington streets—is the city’s business district and home to many major corporations. The pointy Transamerica Pyramid at Montgomery and Clay streets is the district’s most conspicuous architectural feature. To its east sprawls the Embarcadero Center, an 8 1/2-acre complex housing offices, shops, and restaurants. Farther east still at the water’s edge is the old Ferry Building, the city’s pre-bridge transportation hub. Ferries to Sausalito and Larkspur still leave from this point. However a renovation in 2003 made the building an attraction all its own; today it’s packed with outstanding restaurants and gourmet food—and wine-related shops, and surrounded by a farmers’ market a few days a week that attracts residents and top chefs looking to fill their fridges.

Nob Hill & Russian Hill -- Bounded by Bush, Larkin, Pacific, and Stockton streets, Nob Hill is a genteel, well-heeled district occupied by the city’s power brokers and the neighborhood businesses they frequent. Russian Hill extends from Pacific to Bay streets and from Polk to Mason streets. It contains steep streets, lush gardens, and high-rises occupied by both the moneyed and the bohemian.

Chinatown -- A large red-and-green gate on Grant Avenue at Bush Street marks the official entrance to Chinatown. Beyond lies a 24-block labyrinth, bordered by Broadway, Bush, Kearny, and Stockton streets, filled with restaurants, markets, temples, shops, apartment buildings, and a substantial percentage of San Francisco’s Chinese residents. Chinatown is a great place for exploration all along Grant and Stockton streets, Portsmouth Square, and the alleys that lead off them, like Ross and Waverly. Chinatown’s incessant traffic and precious few parking spots mean you shouldn’t even consider driving around here.

North Beach -- This Italian neighborhood, which stretches from Montgomery and Jackson streets to Bay Street, is one of the best places in the city to grab a coffee, pull up a cafe chair, and do some serious people-watching. At night, the restaurants, bars, and clubs along Columbus and Grant avenues attract folks from all over the Bay Area. Down Columbus Avenue toward the Financial District are the remains of the city’s Beat Generation landmarks, including Ferlinghetti’s City Lights Booksellers. Broadway Street—a short strip of sex joints—cuts through the heart of the district. Telegraph Hill looms over the east side of North Beach, topped by Coit Tower, one of San Francisco’s best vantage points.

Fisherman's Wharf -- North Beach runs into Fisherman’s Wharf, which was once the busy heart of the city’s great harbor and waterfront industries. Today it’s a popular tourist area with little, if any, authentic waterfront life, except for a small fleet of fishing boats and some noisy sea lions. What it does have going for it are activities for the whole family, with honky-tonk attractions and museums, restaurants, trinket shops, and beautiful views everywhere you look.

The Marina District -- Created on landfill—actually rubble from the 1906 earthquake—for the Panama Pacific Exposition of 1915, the Marina District boasts some of the best views of the Golden Gate, as well as plenty of grassy fields alongside San Francisco Bay. Elegant Mediterranean-style homes and apartments, inhabited by the city’s well-to-do singles and wealthy families, line the streets. Here, too, are architectural wonder the Palace of Fine Arts, the artcentric warehouses of Fort Mason, and dog and jogger-lover’s paradise, Crissy Field. The main street is Chestnut, between Franklin and Lyon streets, which abounds with shops, cafes, and boutiques. Because of its landfill foundation, the Marina was among the hardest-hit districts in the 1989 quake.

Cow Hollow -- Located west of Van Ness Avenue, between Russian Hill and the Presidio, this flat, graze-able area supported 30 dairy farms in 1861. Today, Cow Hollow is largely residential and largely post-colligate young professionals. Its two primary commercial thoroughfares are Lombard Street, known for its relatively cheap motels, and Union Street, an upscale shopping sector filled with restaurants, pubs, cafes, and boutiques.

Pacific Heights -- The ultra-elite, such as the Gettys and Danielle Steel—and those lucky enough to buy before the real-estate boom—reside in the mansions and homes in this neighborhood. When the rich meander out of their fortresses, they wander down to the neighborhood’s two posh shopping and dining streets—Fillmore or Union—and join the pretty people who frequent the chic boutiques and lively neighborhood restaurants, cafes, and bars.

Japantown -- Bounded by Octavia, Fillmore, California, and Geary streets, Japantown shelters only a small percentage of the city’s Japanese population. At its epicenter is Japan Center, a dated but fun 2-block indoor mall featuring Japanese knickknack shops, bookstores, noodle restaurants, and more. Duck inside one of the photo booths and take home a dozen Hello Kitty stickers as a souvenir.

Civic Center -- Although millions of dollars have gone toward brick sidewalks, ornate lampposts, and elaborate street plantings, the southwestern section of Market Street can still feel a little sketchy due to the large number of homeless people who wander the area. The Civic Center at the “bottom” of Market Street, however, is a stunning beacon of culture and refinement. This large complex of buildings includes the domed and dapper City Hall, the Opera House, Davies Symphony Hall, the new SFJAZZ building, and the Asian Art Museum. The landscaped plaza connecting the buildings is the staging area for San Francisco’s frequent demonstrations for or against just about everything.

SoMa -- This expansive flatland area within the triangle of the Embarcadero, Hwy. 101, and Market Street is characterized by wide, busy streets and old warehouses and industrial spaces with a few scattered underground nightclubs, restaurants, and shoddy residential areas. But over the years the addition of the Museum of Modern Art, Yerba Buena Gardens, the Jewish and African Diaspora museums, Metreon, and AT&T Park, and later offices for major companies like Twitter have infused the gritty area with multimillion-dollar lofts, fancy high-rise residences, and a bevy of new businesses, hotels, restaurants, and nightclubs.

Mission District -- Mexican and Latin American populations made this area home, with their cuisine, traditions, and art creating a vibrant cultural area, but more recently, the Mission is home to San Francisco’s hipsters and hippest restaurants. Some parts of the neighborhood are still poor and sprinkled with the homeless, gangs, and drug addicts, but young urbanites have declared the place their own, lured by the endless oh-so-hot restaurants and bars that stretch from 16th and Valencia streets to 25th and Mission streets. Less adventurous tourists may just want to duck into Mission Dolores (San Francisco’s oldest building), cruise past a few of the 200-plus amazing murals, and head back downtown. But anyone who’s interested in hanging with the hipsters and experiencing the hottest restaurant and bar nightlife should definitely beeline it here.

The Castro -- One of the liveliest districts in town, the Castro is practically synonymous with San Francisco’s gay community, who moved here back in the 1970s, turning this once Irish working-class neighborhood into a bustling hotbed of shops, bars, and restaurants. Located at the top of Market Street, between 17th and 18th streets, the Castro offers a thoroughly entertaining dose of street theater, and while most businesses cater to the gay community, it’s more than welcoming to open-minded straight people.

Haight-Ashbury -- Part trendy, part nostalgic, part funky, the Haight, as it’s most commonly known, was the soul of the psychedelic free-loving 1960s and the center of the counterculture movement. Today, thanks to a never-ending real estate boom, the gritty neighborhood straddling upper Haight Street on the eastern border of Golden Gate Park is more gentrified, but the commercial area still harbors all walks of life. But you don’t need to be groovy to enjoy the Haight—the ethnic food, trendy shops, and bars cover all tastes. From Haight Street, walk south on Cole Street for a more peaceful neighborhood experience.

Richmond & Sunset Districts -- San Francisco’s suburbs of sorts, these are the city’s largest and most populous neighborhoods, consisting mainly of small homes, shops, cafes, and neighborhood restaurants. Although they border Golden Gate Park and Ocean Beach, few tourists venture into “the Avenues,” as these areas are referred to locally, unless they’re on their way to the Cliff House, zoo, beach, or Palace of the Legion of Honor Museum.

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.