You got the date. That’s the easy part. Now comes time to figure out where to go. It’s a torturous exercise that sends many a guy and gal scouring Yelp for hours like grandpa sweeping the sand with a metal detector. But fear not! We’ve compiled a list of all-in-one date nights that’ll allow you to pop in for a pre-dinner drink, take a short stroll to a neighboring restaurant and then escort the sweetheart to a sweet treat, all without stepping foot inside a vehicle.

Los Gatos

Enoteca La Storia
Oak and Rye
Dolce Spazio Dessert Cafe

With more than 200 types of wine to choose from, starting the night off at Enoteca La Storia is sure to impress—unless you don’t know your pronunciations. Then we suggest playing it cool and sticking with helpful staff suggestions. After a glass, head over to Oak and Rye to continue the Italian theme with their creative pizzas—the Scotty 2 Hottie (crushed tomato, mozzarella, basil, sopressata, pepperoncini oil and honey) is a must try—before completing the night with a rich gelato and sorbetto at Dolce Spazio.

Palo Alto

La Bodeguita Del Medio

Spice up the usual pre-dinner drinks by sampling the sparkling and wine flights at Calave. Then head two blocks up California Avenue to La Bodeguita Del Medio. It may be a mouthful to say, but the taste buds will appreciate dishes like Tierra y mar-marinated skirt steak, coconut crusted shrimp, sofrito mashed potatoes, grilled asparagus and avocado-cilantro pesto. Check out Baume, still fresh off of last year’s 2 Michelin star win, for desserts with a molecular twist.

San Jose

Black Sheep Brasserie

Aqui is a staple for any night out in Willow Glen, which is perhaps why the famous Swirl and Industrial Strength Margarita are made in bulk. (Warning: We recommend sticking to one if drinks will be served with dinner.) A quick stroll down Lincoln Avenue leads to the Black Sheep Brasserie, Metro’s most recent Best New Restaurant winner. A night in Willow Glen is not complete without a stop at the hottest new dessert trend that’s part-treat, part-art: Icicles.


Rock Bottom Brewery
Orchard City Kitchen
Sugar Butter Flour 

Craving a cold one for date night? Head out to Rock Bottom Brewery in the Pruneyard for a choice of award-winning brews including the Bottom’s Up Kolsch, only available for a limited time. What goes better with beer than bacon? Nothing. Start off dinner at Orchard City Kitchen with the addictive Triple B—biscuits, bacon and honey butter—and sample as many shareable plates as possible before finishing up at Sugar Butter Flour.

Santa Clara

Mission City Grill
Copenhagen Crown Bakery & Deli

Taplands has made a name for itself as a must-visit destination for local beer lovers, with its 24 taps constantly rotating like a tasting roulette. Whet the appetite with some charcuterie, which comes heaped on a cutting board with gherkins, marmalade and a dab of stone-ground mustard. But resist the urge to polish it off because the dinners at Mission City Grill come hearty and hale, including prime rib on the weekends. By the time it’s time for dessert, there’s only room for a bite or two, so finish the night off with a puff pastry from Copenhagen Crown Bakery.


The Patio Bar
House of Pho

El Camino Real offers a wild time by starting at The Patio Bar, a laid-back dive with, as the name implies, plenty of outdoor seating. Known for its stiff cocktails, keep things casual but delicious with dinner at House of Pho. The eponymous broth, fried chicken and rice plates don’t disappoint. For dessert, head over to Cocohodo to sample its signature walnut pastry (ho do gwa ja) along with a sweet-and-steamy green tea latte. A mug of sea salt coffee can also provide a little pick-me-up before the drive home.


East Coast Alice
Café Pink House

If there’s time to kill before a dinner reservation, pass the time with a proper wine tasting at Uncorked, whose friendly staff guides customers through the store’s global wine selection. Nothing goes better with a bold red than traditional Italian fare, and East Coast Alice guests have their pick of a culinary repertoire that includes gooey Burrata, pan-fried veal parmesan, house-made gnocchi and thin-crust pizzas. Try and hold off on dessert until nearby Café Pink House, where the night can end with panna cotta or creme brulee while listening to live jazz.

Mountain View

Stein’s Beer Garden
Alexander’s Patisserie

The corner of Villa and Castro streets provides an anchor for this night. Start with Stein’s, whose impressive beer list features 31 craft and import beers from around the globe, including 16 house staples and 15 rotating taps. A must-try for the future is Firestone Walker Opal. Pokeworks takes an elegant twist on the poke trend, as craft bowls are filled with the typical assortment of ahi tuna and salmon along with unique options such as wasabi shrimp and scallops, and sweet chili tofu. Alexander’s Patisserie offers a variety of sweet endings for any night, but look out for their 15 macaron flavors.