Long overshadowed by its dolled-up big sister across the Bay, Oakland is its own town. Even as its status as one of the most diverse cities in the country is threatened by tech-boom-era gentrification, its thrilling cultural heterogeneity remains its greatest strength. The city’s rather dull skyline belies its architectural splendor — from glamorous movie palaces to the Kevin Roche-designed midcentury-modern Oakland Museum of California to the 135-acre Mills College campus, where Beaux-Arts and Spanish Colonial Revival buildings are set among eucalyptus trees. The western terminus of the Transcontinental Railroad and a thriving port, Oakland remains a proud working-class town even as new developments, like the huge Brooklyn Basin project, remake its waterfront.
1. GET HAPPY, 3 P.M.
For a California-centric selection of more than a dozen craft beers on tap and a human scale game of Jenga, head to Portal. Its backyard patio, ringed with sparkling white lights, has a view of Lake Merritt. The line for the fabulous brunch here is almost always long. So skip it and try the restaurant’s “garbage bread,” made from pizza dough, proofed overnight and rolled into a burrito-Stromboli mash-up stuffed with either pepperoni and sausage, herbs and ricotta, or vegetables ($14) at happy hour. Afterward, walk north around the lake, a wildlife refuge established in 1870. Look for rare white pelicans, including one year-round resident named Hank.
2. FIRED UP, 6 P.M.
For dinner, splurge at Camino, where the food is cooked by wood-fire, the seating is communal and tips are not accepted — an effort its husband-wife owners, Russell Moore and Allison Hopelain, have helped spearhead nationally. The restaurant (its prices, mainly) has its detractors, but as a direct descendant of Chez Panisse, where Mr. Moore, the chef, worked for two decades, it’s hard to find more emblematic Northern California cooking in its purest, casual-yet-refined form. With one fireplace and one wood oven continually burning, each night’s menu features three entrees: typically one meat (rib-eye steak and slow-cooked short ribs with grits, green beans and fried sunchokes, $42, for example), one fish (like local ling cod with green beans, tomato confit, cilantro and saffron broth, $37) and a vegetarian offering. Camino’s new cookbook, “This Is Camino,” makes a fine souvenir.
3. GET ARTSY, 8 P.M.
Once a month, the decade-old Oakland Art Murmur takes over the Uptown neighborhood. A First Friday art walk (6 to 9 p.m.) includes dozens of galleries and venues and a street party that embodies the spirit of this changing city. (Quieter afternoon “Saturday Strolls” are held every week.) In Uptown’s Fox Square, seek out the “Remember Them: Champions for Humanity” sculpture, a four-piece, 25-foot-tall bronze work that honors 25 humanitarians. The landing-place for generations of black migrants from the American South, Oakland has a storied jazz tradition. The Sound Roomhosts local blues and soul singers, Big Band and West Coast Latin Jazz groups and international acts. Tickets start at $10.
4. INTERNATIONAL BREAKFAST, 9 A.M.
By Cesar Chavez Park in a tiny orange stucco building in Fruitvale, Taqueria Campos feels like a modest Mexican home, where the tortillas are fresh and stockpots are simmering with the Jalisco specialties of pozole, menudo and goat birria — three meaty soups that provide a warming winter breakfast. Another East Side option is Saigon Deli Sandwich & Taco Valparaiso. With co-owners from Vietnam and Mexico, respectively, this banh mi shop and taco stand in one serves everything from pork combination sandwiches with pâté and head cheese to fish or lengua (tongue) tacos and Mission-style burritos. A meal at either cash-only restaurant runs less than $10.
5. MORBID MORNING, 10 A.M.
The Frederick Law Olmsted-designed Mountain View Cemetery prides itself on “transcending the division between man and nature” with a parklike landscape of California live oak, Italian cypress, Lebanese cedar, Italian stone pine and palm trees in the Piedmont Hills. The cemetery, which dates to the 1860s, has tombstones of some of the state’s most influential residents, including Julia Morgan, who designed the nearby Chapel of the Chimes as well as Hearst Castle. On the second and fourth Saturdays of each month, there are free docent-led tours at 10 a.m.
6. TEMESCAL ALLEY, 11 A.M.
Tucked away in the Temescal neighborhood, two pedestrian alleys are home to shops that feel as if they jumped off Etsy’s home page. Along with boutiques selling twee teapots and handmade coat racks, there’s Book/Shop, a tiny store and print design studio that treats its texts like art objects. At Marisa Mason Studio, the designer Marisa Haskell riffs on the hippie-era appropriation of indigenous jewelry, creating pieces that embrace bohemian California’s unselfconscious borrowing from Southwestern and Mexican folk art. Stop at the Kickstarter-funded Curbside Creamery, where five of the dozen or so varieties — from traditional mint chip to the wonderful Thai tea flavor — are vegan, made with cashew milk (scoops start at $3).
7. IN THE SWING OF IT, NOON
Trapeze Arts is one of a handful of circus schools in the United States. Founded in 1994, students have gone on to Cirque du Soleil and Ringling Bros. and Barnum & Bailey Circus. The 13,000-square-foot warehouse space is open to the public to try their hand at trampolines and trapezes, hoops and ropes, tight wire and unicycle. Single classes start at $35, reservations required. Nearby, the Crucible teaches three-hour “taster” classes ($135), offering introductions to industrial arts like welding and sand casting.
8. SOMETHING UNEXPECTED, 3 P.M.
On a West Oakland sidestreet with graffiti and industrial lots, the sophisticated Korean restaurant FuseBoxopens at 2 p.m. on Saturdays for what the owners call an “extended happy hour” (through 5:30 p.m.). Try the spicy, rice-flour-battered “KFC” — Korean fried chicken — and a beer for $8, or the pig ear fries and beer or wine for $7. The beans used in the house tofu come from the nearby Hodo Soy Beanery. In the winter, FuseBox offers blankets and hot sake for those who sit outside beside fire pits.
9. THE NEW OLD TOWN, 5 P.M.
At Umami Mart, a sublime Japanese kitchen and barware shop, food, drink and design intersect. Its Bottle Shop, which focuses exclusively on Japanese beer, sets it apart. Umami Mart’s sake club, Sake Gumi, delivers two bottles of sake, along with tasting notes and pairing suggestions ($29, or $75 monthly). Afterward, head to Swan’s Market, a historic “housewives’ market,” with an exceptional food court, from the Japanese set lunches at B-Dama to The Cook and Her Farmer’s mind-blowing oyster po’ boy. Miss Ollie’s is an Afro-Caribbean restaurant where the jerk shrimp are big and scorchingly spicy ($12.50) and the skillet-fried chicken (a generous portion for $17.75) is among the best in the Bay Area.
10. ON (AND OFF) BROADWAY, 8 P.M.
In a city with an abundance of Art Deco-era movie palaces, the Paramount has transformed itself into a multipurpose venue for everything from classics like “The Wizard of Oz” to performances of “The Nutcracker” and the Oakland Interfaith Gospel Choir. Alternatively, head to the New Parkway Theater, where there are love seats and vintage chairs and a cafe with local wine and beer. Shows ($8) range from blockbusters like “Straight Outta Compton” to viewings of the presidential debates.
11. VINTAGE NIGHT LIFE, 10:30 P.M.
The Alley is a well-worn piano bar with decades of business cards papering its walls and the famous (some might say notorious) Rod Dibble playing a selection of some 4,000 standards and show tunes. Mr. Dibble has been at his station since 1960, making him an Oakland institution. The crowd is as eclectic as they come, and all are invited to sing, making it karaoke meets cabaret in a time capsule. Then consider making a pilgrimage to Cafe Van Kleef. Its owner and namesake, known as the “Uptown godfather,” died in September, but his bar and its famed greyhound cocktails survive. Van Kleef’s location — walking distance from City Hall — made it a hangout for politicos, including the former mayor and current governor Jerry Brown. On weekends, live music ranges from Oakland Dub to folk to R&B.
12. HIT THE HARBOR, 9 A.M.
Calling it brunch might be pushing it. Starting at 9 a.m., the Fat Lady serves breakfast with booze. Dimly lit, with dripped-wax-draped candelabras, mismatched paintings and a long bar, this 1970s-era Jack London Square institution is housed in a former (circa 1880s) brothel and built on myth and a mean corned beef hash ($14). After breakfast, walk to the waterfront to Sunday’s farmers’ market. You can take a docent-led dockside tour ($10) of the 1934 U.S.S. Potomac, Franklin Delano Roosevelt’s 165-foot “Floating White House.” Then drive through the industrial maze of shipping containers, idling trucks and towering cranes to Middle Harbor Shoreline Park, where the views of San Francisco’s skyline are unbeatable.
With a prime location in Jack London Square, steps from the ferry to San Francisco, Joie de Vivre’s Waterfront Hotel (10 Washington Street, 510-836-3800; jdvhotels.com) has a retro nautical theme, a complimentary wine and cheese hour each evening and prices starting at $209.
Despite the rapid change in recent years, Oakland’s hotel offerings remain relatively meager. Just across the border in neighboring Berkeley, the Claremont Hotel Club and Spa (41 Tunnel Road, 510-843-3000; claremontresort.com) is an East Bay institution. Opened in 1915, the resort has two heated lap pools, tennis courts and a recently renovated 20,000-square-foot fitness center. Rooms start at $191.