The Best Date Ideas in San Jose
Ten date ideas in San Jose, from a mansion with doors that open onto walls and a night of pinball to a hillside wine tasting, a drive-in double feature, and a canyon hike.
A good date in San Jose can mean pinball, a drive-in double feature, wine on a hillside, or a few hours on the trail. These ten ideas give you plenty to do together, whether you want something hands-on, outdoors, or a little unexpected.
Winchester Mystery House

Explore the Winchester Mystery House together, a 160-room mansion in west San Jose known for doors that open onto walls and stairways that lead to the ceiling. The 65-minute Mansion Tour takes you through 110 rooms, and your ticket also includes access to the gardens.
Buy tickets online ahead of your visit. In October, Halloween Haunt decorations are set up in the house and may show on tours.
Tickets online
Topgolf San Jose

Take swings together at Topgolf San Jose, where clubs are provided and the balls score themselves. The complex has three floors with 120 all-weather bays, a rooftop terrace, a bar and restaurant, and an arcade.
Booking a bay online through Book a Bay can cost less than walking in. Bays stay open until midnight Sunday through Thursday and until 1am on Friday and Saturday.
Book a Bay online
$
West Wind Capitol Drive-In
Catch a double feature from your car at West Wind Capitol Drive-In in south San Jose, a fun night out. First-run films play on huge digital screens, and you can bring your own food or use the snack bars.
Pick an evening other than Tuesday for a quieter night, since Tuesday is billed as family fun night.
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Alamitos Vineyards
Alamitos Vineyards in New Almaden pours its tastings outdoors from a 1964 Silver Streak trailer, facing Quicksilver Park and the Almaden Reservoir across the hillside. The flight covers four seasonal wines. Dinner at La Foret in Almaden Valley makes a natural next stop.
Tastings run Saturday and Sunday from 11am to 4pm, by reservation only through the website. Guests must be 21 or older, and seating shrinks in fall and winter, with bookings filling several weeks ahead.
By reservation on the website
$$$$
Plantlush

Build a terrarium together at Plantlush, a Willow Glen plant shop that runs beginner-friendly workshops. You leave with a living piece of your own making.
Open terrarium workshops run 90 minutes, and the Date Night Terrarium Workshop is for two. Book your seats online.
Workshops booked online
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Rosicrucian Egyptian Museum

Step into a building inspired by the Temple of Amon at Karnak, where the artifacts on display make up the largest ancient Egyptian collection in Western North America. Outside, the Peace Garden and Labyrinth are open from 8am to sunset.
The museum is open Friday through Sunday. Buy tickets online for timed admission.
Tickets online
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Miniboss

Challenge each other at Miniboss, a downtown arcade bar with 32 arcade machines and 12 pinball machines. We'd split the Miniboss Combo pizza, with mushrooms, olives, pepperoni, sausage, and bacon jam, and add a Piccolo or Die cocktail, made with dark rum, ube, milk tea, and matcha whipped cream.
Miniboss is open Wednesday through Sunday, opening at 5pm most nights and at 2pm on Sunday.
$$$
Left Bank - Santana Row

Wander Santana Row, an open-air district in west San Jose with more than 50 shops and 30 restaurants. The parks and plazas host live music and outdoor yoga, and the CineArts theatre is there for a movie. The boutique Hotel Valencia is also on the Row.
$$$
The Tech Interactive

Explore more than 100 hands-on experiences and an IMAX Dome Theater at The Tech Interactive, a science museum downtown. The weekly LASERS! shows pair lasers with hit music.
Admission includes one IMAX film. Check the daily schedule before you go, since hours vary by season.
Alum Rock Park

Hike through a 720-acre canyon park in east San Jose with about 13 miles of trails. The Creek Trail is an easy 4-mile route, while the South Rim Trail is a moderate 3 miles with views of the valley. On the valley floor you will also find the historic mineral baths and grottos.
Bring a picnic, since tables and barbecue pits are in the park.
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